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14 Essential Travel Tips for the Florida Keys You NEED Before You Go

Here are my top travel tips for the Florida Keys to help you plan and make the most of your holiday in Florida. It’s an amazing place to be, but it helps to be prepared!

The Florida Keys offers beautiful beaches and lots of adventures. There’s so much to do and see in the Keys though, that you need to read my travel tips for the Florida Keys before you go.

I’ve answered all the main questions about the Florida Keys I’ve been asked over the years, and a few I’ve just made up that I thought you’d like to know. I want to help you have the best trip to the Florida Keys possible!

So, here are all my travel tips for the Florida Keys for you to enjoy.

Travel tips for the Florida Keys

If the answer to your question isn’t here, just let me know in the comments below. I love to give travel advice for the Florida Keys!

1. Where are the Florida Keys?

The Florida Keys are a series of tropical islands that are located off the southern coast of Florida. The islands begin about 15 miles south of Miami and continue for over 120 miles. Key West, Marathon, and Key Largo are a few of the most popular islands found in the Florida Keys.

2. How do I get to the Florida Keys?

The fastest way to get to the Florida Keys is definitely flying to the islands from one of the Florida airports – either Tampa, Fort Lauderdale or Miami. However, there is another option…

One of the most unique things about the Florida Keys is that it is possible to drive to the islands via the Florida Keys Overseas Highway which stretches 113 miles from the mainland of Florida well into the Keys.

Travelling on the Overseas Highway from Miami to Key West will give you the opportunity to see some of the most varied and beautiful scenery in the state of Florida. The highway includes 42 bridges that cross the ocean between each island. It also travels through an area of water-rooted mangroves and another area populated by grand pine trees. 

This would be great as part of a longer Florida road trip – click the link to find out the top spots to visit. If you want travel tips for the Florida Keys, then driving there would have to be the number one!

3. What are the Florida Keys known for?

The Florida Keys are located on a coral cay archipelago. This makes the Keys an excellent place for diving and snorkelling. Hundreds of thousands of people travel to the Florida Keys every year to partake in the diving and snorkelling among the abundant wildlife in the coral reefs surrounding the Keys.

You’ll easily find diving companies and schools on almost every island in the Florida Keys. Each island offers its own unique underwater attractions that you can dive amongst including extraordinary reef formations and a variety of shipwrecks to explore.

In addition to recreational water activities, the Florida Keys are home to lots of unique attractions. Each island has its own arts and culture to experience but there is no shortage of arts, theatres, museums, and activities to check out in the Keys. 

4. Can I go diving in the Florida Keys?

Yes! Diving and snorkelling in the Florida Keys is also a great opportunity to get up close and personal with a variety or marine wildlife. These activities are some of the most popular in the Keys.

Divers in the area encounter angelfish, barracudas, groupers, moray eels, grunts, and damselfish as well as a plethora of other wildlife species. 

Activities like this 3-hour Key West Catamaran and Snorkelling tour are a great way to experience snorkelling in a safe way, with a company who knows what they’re doing.

“Enjoy a day exploring the beautiful waters of the Florida Keys on a luxurious catamaran. Go snorkelling in tropical waters, and try jet skiing, parasailing, kayaking, and paddle-boarding. – CATAMARAN TOUR ON GETYOURGUIDE (click for prices)

The most important travel tip for the Florida Keys is to get out on the water!

Watch my video for more fun ideas and travel tips for the Florida Keys

5. Can I go fishing in the Florida Keys?

The Florida Keys are also famous for the fishing opportunities that you can find on the islands. In fact, Islamorada is known as the Sport Fishing Capital of the World. Islamorada’s location uniquely creates a wide diversity of fish that can be caught for sport.

In addition, the powerful Gulf Stream is located about ten to twenty miles off the shores of most of the islands in the Keys. This current brings seasonal fish to the islands such as sailfish, marlin, and tuna. 

There are a number of companies that provide fishing tours throughout the Keys. You can also use similar companies to engage in deep sea fishing outside of the Keys. If you’re fishing with one of these companies, you will not need a fishing license. However, a saltwater fishing license if required to fish independently in the Florida Keys.

READ MORE: The Best Festivals in Florida

6. What is the ‘Dry Tortugas National Park’?

Key West is home to lots of parks but probably the most famous is the Dry Tortugas National Park . The US National Park is made up of seven small islands surrounding Key West. Within the park is the historic Fort Jefferson which served as a prison during the Civil War.

Take the time to tour the fort and learn about the history of the area. The beaches in Dry Tortugas National Park are breathtaking with powdery white sand and crystal blue waters. They’re the perfect place to spend an afternoon on the beach. 

You can see the rest of the best beaches in the Florida Keys here .

7. How can I experience nature in the Florida Keys?

A variety of eco tours are offered throughout the Florida Keys, and there are some great tours available. Almost the entirety of the Florida Keys lies within the Everglade National Park. The tours offered through Garl’s allow for hiking, fresh water paddling, and saltwater paddling. It is one of the best ways to really see the wildlife and beauty in the everglades.

There are multiple locations throughout the Florida Keys that offer dolphin tours so that you can watch dolphins in the natural habitats. In some places you may even be able to touch, swim, and interact with dolphins. 

Check out these eco tours in the Florida Keys for more ideas…

• Key West Dolphin Watch and Snorkel Eco Tour
• Key West: Eco Safari Tour with Snorkelling
• Key West Island Adventure Eco Tour

If you want to know more about what to do in the Everglades National Park , click that link!

8. What should I eat in the Florida Keys?

Since the Florida Keys are islands, plan to eat lots of seafood. The Keys have some specific seafood varieties that they are known for.

– Key West pink shrimp is one the most popular options in the Florida Keys. It is often described as sweeter than other varieties.

– Stone crabs are also popular in the Keys during the stone crab season which lasts from October 15 to May 15 every year.

– Fresh fish is also available year around.

There is no lack of amazing seafood restaurants throughout the Keys, in fact I’ve nailed down some of the best restaurants in the Florida Keys for your trip. Also, Key Lime Pie is a BIG deal here. Check out this Key Lime Piebicycle tour to make sure you get the best ones!

You want my travel advice for the Florida Keys? Eat as much as possible!

9. Are water sports available in the Florida Keys?

There are a variety of water sports and activities in the Florida Keys.

Boating, sailing, and kayaking are popular choices. There are designated areas where you can jet ski and ski. Parasailing is very popular in the Florida Keys as well. Whether you are fishing, diving, kayaking, or parasailing, there are tons of options for an adventure on the water throughout the Florida Keys.

Key West and Key Largo offer the widest variety of options to choose from.

10. What other activities in the Florida Keys are there?

Key West is one of the most popular and well-known islands in the Florida Keys. With lots of free and family-oriented activities, this island is a popular destination for family groups. 

You can spend a day in Key West , a month, or just do as some do, and go and live there!

There are loads of fun things to do in the Florida Keys .

Most people visit the Sport Fishing Capital of the World, the island is Islamorada, to partake of the fishing opportunities. However, Islamorada has a lot more to offer than just fishing. Check out the Theater of the Sea when you visit Islamorada. The Theater of the Sea is a unique marine mammal park that is made up of lush lagoons and beautiful tropical gardens. It is home to dolphins, sharks, sea turtles, sea lions, stingrays, and alligators. The park is designed to let visitors get up close and personal with wildlife native to the Florida Keys. You’ll have the chance to swim with dolphins and sharks and meet sea turtles and alligators face to face.

The African Queen Canal Tour in Key Largo is a great choice. The African Queen is a historic vessel used in the 1951 movie of the same  name. Fans can now take a tour aboard the vessel through the Port Largo Canal and enjoy the views.

In addition to recreational water activities, the Florida Keys are home to lots of unique attractions. Each island has its own arts and culture to experience but there is no shortage of arts, theatres, museums, and activities to check out in the Keys. You can check  allcruisehotels  for accommodations if you’ll be staying to visit the sights before hitting the road.

READ MORE: Fascinating Florida Keys Facts to Know Before You Go

11. What can you do at night in the Florida Keys?

If you’re looking for Key West nightlife then click on that link to be taken to all the best options for your evening entertainment.

If you’re looking for something a little different, then this two-hour sunset sail with live music in Key West would be a great thing to do in the evening, and give a unique perspective on Key West.

“Experience the magnificent Key West sunset from the water on this all-inclusive sailing trip. Indulge in spectacular views, unlimited drinks and appetizers, and live music. Enjoy the perfect end to your day in the Keys.” –  TWO HOUR SUNSET SAIL on GET YOUR GUIDE (click to check prices)

12. Which island should I stay on in the Florida Keys?

Each of the islands that make up the Florida Keys is beautiful and have their own unique offerings. Choosing where to stay will be influenced on the kind of vacation you are seeking.

If you are looking for a safe, family friendly location, Key West is a great option and has a wide variety of accommodations to meet every budget.

Key Largo is also a great choice for families. Both islands have lots of attractions and activities.

If you are looking for a more leisurely stay, try Marathon which is home to multiple golf courses, marinas, and tennis clubs. Many of the most popular accommodations on Marathon are golfing and tennis resorts. Marathon is not quite as active and fast-paced as Key West and Key Largo but traveling to the other islands for a quick adventure is very easy.

While Islamorada does not have any golf courses, it is home to several small, intimate resorts. This island would be a perfect stay for a couple looking to get away for a while.

Read my post on where to stay in the Florida Keys for more tips and advice on where to be.

13. What else do the Florida Keys have to offer?

While the watersports, fishing, diving, and nature tours will fill the majority of your days, there are also several other options in the Florida Keys. Throughout the keys you will find beautiful spas where you can rest and relax. What better way to finish off an active day than with a relaxing hot stone massage? Whether you’re looking for body treatments, facials, or massage, there is no shortage of spa offerings on almost all of the major islands of the Florida Keys. 

Fitness is also a priority in much of the Keys. If you want to maintain your fitness routine while you are on vacation, you will be able to book yoga sessions on the beach, spin classes, or even pilates. There are fitness centres Key West and Key Largo where you can purchase daily or weekly memberships as well.

While shopping is not the first thing that comes to mind when you think about the Florida Keys, locally-owned artisan shops offer lots of unique, hand-crafted shops. Throughout the Keys you will find beautiful jewelry, shell shops, and a plethora of souvenirs. Spend an afternoon perusing the local shop and see what kind of treasures you can find.

14. Buy some souvenirs

When you’re in Florida, you’ve got to pick up some souvenirs. Here are some of the best things to buy in Florida to remember your trip by. You’ll find them all across the Sunshine State.

The Florida Keys – something for everyone !

Whether you just want to relax on the beach or spend the day on the water, the Florida Keys has something for everyone. With a wide range of water activities, eco tours, beautiful scenery, and flavourful seafood, it is the perfect vacation spot to visit  this summer. 

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Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

10 Comments

Can’t wait to go to Florida Keys! Your travel tips, best restaurants and so much more are great! Would appreciate any and all Florida Keys travel info links you have. I am planning to go in late summer or fall of 2022. Thanks, keep me posted on your travel links!

Oh that’s great to hear. I’m glad to be of service! As you can see there’s loads of advice for the Florida Keys on this site – I’ve put it all out there, so enjoy!

Please send info of places to stay…the best!

Hi Sandy, ok, I will get on to that ASAP! There are some really great places to stay in the Keys!

@VickyFlipFlop, @LooeKeyReefResort is great!

Oh, thanks for letting me know. I’ll have to try it one day!

Excellent article. Planning a trip to the Keys with my daughter and granddaughter next year.

Don’t forget the Key West Express from Fort Myers to the bight in Key West.

Great company, beautiful trip by boat and you’re relaxed when you arrive.

Ok, good shout! I hope people read the comments and get your tip off!

There’s a food tour called Florida keys Food tour in Islamorada. Takes you to several of the best local restaurants, and art gallery, Fl Keys Brewery, and provides lots of history.

Oh that sounds like a great idea. I love a food tour to show a bit more of a destination. Also a great way to just eat a little bit of everything!

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The Ultimate Travel Guide for the Florida Keys: Insider Tips for the Perfect Getaway

The Florida Keys offer a captivating adventure through a chain of tropical islands that stretch about 120 miles off the southern tip of Florida. As a world-renowned destination, they provide a unique blend of natural beauty, historical sites, and cultural experiences. Embarking on a road trip along the Overseas Highway, travelers thread their way from Key Largo to Key West , and in doing so, discover the distinct personality of each individual key.

Each island in the Florida Keys serves up its own flavor of paradise. Key Largo is often celebrated as a diver’s haven, home to the only living coral barrier reef in the United States. Further down the highway, the Lower Keys are famous for their laid-back atmosphere and the opportunity to see the petite Key deer in their natural habitat. At the end of the island chain, Key West exudes a vibrant energy that has attracted writers, artists, and vacationers for decades.

Along this drive, the sparkling waters of the Atlantic Ocean and Gulf of Mexico frame the horizon, inviting travelers to indulge in a variety of water sports, from snorkeling and fishing to sailing. Offshore excursions to the Dry Tortugas National Park reveal a secluded world of marine life and the impressive 19th-century Fort Jefferson. With the right itinerary, a journey through the Florida Keys can be both exhilarating and relaxing, tailored to any traveler’s desire to find their own joie de vivre.

Exploring the Florida Keys

The Florida Keys offer an enchanting array of islands each with distinct features, beckoning travelers to explore a variety of activities and natural wonders. The chain starts with  Key Largo , popular for its diving opportunities, including the John Pennekamp Coral Reef State Park .

Moving south,  Islamorada claims the title of the sportfishing capital, providing not just thrilling deep-sea excursions but also peaceful beaches and charming seafood eateries. For those captivated by marine life, the Theater of the Sea offers intimate dolphin and sea lion encounters.

Marathon  lies further along the route, a family-friendly harbor providing access to both the Atlantic Ocean and the Gulf of Mexico. The island is perfect for ecological explorations in the Dolphin Research Center and the Turtle Hospital, which emphasize conservation and education.

In the  Lower Keys ,  Big Pine Key  features the National Key Deer Refuge, safeguarding the adorable Key deer. This island grants visitors a quieter slice of the Keys’ life and invites onlookers to pristine natural habitats.

Key West  embodies the quintessence of the Keys’ spirit. Known for its lively Duval Street, historic architecture, sunset celebrations at Mallory Square, and Ernest Hemingway’s residence- now a museum. Warm, crystal-clear waters invite snorkeling, and the beaches pave the way for a quintessential vacation experience.

Lastly, the remote  Dry Tortugas National Park  — accessible by ferry or seaplane from Key West — presents a unique fusion of history and unspoiled nature. Here, the 19th-century Fort Jefferson and undisturbed coral reefs await the avid explorer.

The array of activities available in the Florida Keys ensures a vacation filled with unique experiences, set against the backdrop of an expansive water landscape. From underwater adventures to beach relaxation, each island contributes to the theme of discovery within the enchanting Florida Keys.

Travel Essentials

When planning a trip to the Florida Keys, travelers should consider the optimal season for their visit, the transportation methods available, and the diverse accommodation options to enhance their experience.

Best Time to Visit

The Florida Keys are a year-round destination, but  the best time to visit is between March and May . The weather during these months is warm and pleasant with less rainfall, making it ideal for exploring the islands and soaking in the sun. Visitors should be aware that  June to November marks the hurricane season , which may affect travel plans.

Transportation Tips

Traveling to and within the Florida Keys often involves a scenic road trip along the iconic Overseas Highway (U.S. Route 1), which connects the chain of islands. It’s essential to plan  stops according to the mile markers , which serve as handy references. Renting a car provides the freedom to explore at one’s own pace, but visitors can also consider shuttle services, especially if they intend to partake in activities that might preclude driving, like snorkeling or enjoying the local nightlife.

Accommodation Options

Accommodations in the Florida Keys range from luxury resorts to budget-friendly motels. Key West offers a variety of  hotel  options, including the well-reviewed Margaritaville Beach House for a mid-range budget and the Blue Marlin Motel for a more affordable stay downtown. For those on a road trip, planning  an itinerary with pre-booked hotels  is recommended to ensure availability, especially during peak travel seasons.

Travelers can choose accommodations based on their  trip itinerary  and desired experiences, ensuring a comfortable stay while making the most of their Florida Keys journey.

Iconic Attractions and Activities

The Florida Keys offer an array of iconic attractions and activities, from the storied past of Ernest Hemingway to the sun-soaked shores of Bahia Honda State Park . This guide highlights historical landmarks, natural wonders, and thrilling water sports adventures that define the Keys.

Historical Landmarks

The Keys hold a rich history etched into its many landmarks.  The Ernest Hemingway Home and Museum  in Key West pays homage to one of America’s most iconic writers. Visitors can explore the rooms where Hemingway penned some of his most famous works.  Fort Zachary Taylor Historic State Park  is another must-visit site, offering a glimpse into a fort that played a pivotal role in U.S. history, dating back to the Civil War.

Natural Wonders

Natural beauty abounds in the Keys.  Bahia Honda State Park  features some of the most beautiful beaches in Florida, complete with palm trees and clear waters, ideal for swimming or sunbathing. For wildlife enthusiasts, the National Key Deer Refuge on Big Pine Key provides a sanctuary for the endangered Key deer, a species unique to the Keys. The Everglades, to the north, offers a vast ecosystem teeming with extraordinary flora and fauna.

Water Sports and Adventures

The Keys are synonymous with water activities.  John Pennekamp Coral Reef State Park  is the first undersea park in the U.S., where visitors can  snorkel  or  dive  to explore vibrant coral formations. Boating and fishing are staples in the region, with the warm waters offering ample opportunities for both. Additionally,  Mallory Square  provides an ideal launching point for water sports and is known for its spectacular sunset celebrations.

With the Overseas Highway connecting the islands, travelers can experience panoramic views of the Atlantic Ocean and Gulf of Mexico, making the journey between Key West’s Duval Street and other destinations part of the adventure. Whether by land or sea, the Keys promise unforgettable encounters with their most celebrated attractions and adventures.

Florida Keys’ Culinary Journey

The Florida Keys offers a remarkable culinary scene that entices food lovers with its unique blend of flavors. From delectable seafood to traditional desserts, visitors can embark on a gastronomic adventure that mirrors the islands’ cultural diversity and maritime heritage.

Local Cuisines

Seafood reigns supreme in the Florida Keys, with the freshest catches gracing the tables of many local restaurants.  Conch fritters , a beloved local delicacy, are a must-try for anyone seeking an authentic taste of the region’s culinary tradition. These savory fritters are typically accompanied by a tangy dipping sauce that complements the conch’s mild flavor perfectly.

Another quintessential experience for any visitor is sampling the famous  Key lime pie , a creamy and tart dessert that the Florida Keys claims as its own. Its unique taste comes from the Key lime, a citrus fruit that is smaller and more aromatic than the more common Persian lime.

• Seafood:  shrimp, fish, lobster
• Local Specialty:  conch fritters, served with dipping sauces
• Dessert:  Key lime pie, characterized by its tangy flavor and graham cracker crust

Best Dining Spots

The Florida Keys boast an array of restaurants catering to every palate, from casual seafood shacks to gourmet dining establishments.

• Lazy Days Restaurant:  Offers a picturesque ocean view and a diverse seafood menu.
• Louie’s Backyard:  Serves Caribbean-American seafood in an elegant outdoor setting.

Coffee enthusiasts  should not miss the opportunity to visit  Cuban Coffee Queen , synonymous with Key West. The café is renowned for serving up rich and robust Cuban coffee, a bold drink that reflects the island’s Cuban influences and is the perfect pick-me-up at any time of day.

Accommodations and Lodgings

Travelers seeking to experience the Florida Keys can find a range of accommodations, from lavish resorts to cost-effective hotels . The region offers various options whether one desires luxury amenities or is looking for a budget-friendly stay.

Luxury Resorts

Hawks Cay Resort  is a prime choice for those in search of a luxurious retreat. It provides a blend of relaxation and adventure with amenities such as a saltwater lagoon, multiple pools, and a full-service marina.  Cheeca Lodge & Spa , located in Islamorada, is known for its classic charm, featuring a private beach, a golf course, and oceanfront accommodations. 

The Moorings Village  offers spacious and private beachside living within their lush coconut palm grove, making it an oasis of tranquility. Another notable mention is  Tranquility Bay Beachfront Hotel and Resort , which boasts beach houses and tropical gardens, coupled with dazzling waterfront views. For those venturing near Key Largo,  Baker’s Cay Resort offers a picturesque setting nestled within hardwood forestry on the Gulf of Mexico. 

Budget-friendly Stays

For an economical approach without compromising on the experience, affordable hotels and inns are available throughout the Florida Keys. Visitors can enjoy clean, comfortable accommodations that provide easy access to local attractions and dining options. These budget-friendly lodgings enable travelers to save on stay expenses, allowing them to allocate more towards exploring the abundant recreational activities available in the Keys.

Cultural Experiences

The Florida Keys offer a rich tapestry of cultural experiences ranging from the arts and historical museums to vibrant festivals and daily events that showcase the area’s unique heritage and artistic flair.

Arts and Museums

The  Hemingway Home and Museum  is a must-visit for literature enthusiasts. Located in Key West, this historic house was once the residence of the famed American writer Ernest Hemingway. Visitors can explore the rooms where Hemingway wrote some of his most notable works and learn about his life and time spent on the island.

Another highlight is the  History of Diving Museum , situated in Islamorada. Here, diving aficionados can dive into the world of underwater exploration with exhibits that span the history of diving, including rare diving equipment and artifacts connected to the aquatic world of the Keys.

Theater of the Sea , on Islamorada, is not only a marine mammal park but also a delight for art lovers with its tropical gardens and lagoon-side theater that offers a picturesque backdrop for various artistic representations.

Local Festivals and Events

The Keys are home to a variety of  festivals  that celebrate everything from the maritime history to the local cuisine and arts scene. Signature events include the Fantasy Fest in Key West, an extravagant 10-day party with costumes, parades, and libations, and the Key West Lobsterfest celebrating the start of the lobster season.

The daily  Sunset Celebration  at Mallory Square in Key West has become an iconic event. Artists, musicians, and performers gather to celebrate the end of the day, providing an eclectic cultural experience against the backdrop of a spectacular Key West sunset. This tradition reflects the Keys’ spirit and offers visitors a taste of local life and culture.

Adventure Planning

When exploring the Florida Keys, travelers have the option to craft unique experiences through custom itineraries or simplify their adventure by choosing tour packages. Each approach offers distinct ways to engage with the Keys’ remarkable activities and sights.

Custom Itineraries

For those who prefer a tailored travel experience, constructing a custom itinerary allows for flexibility and personalization. Visitors often target specific attractions such as the iconic  Key West Lighthouse  for historical insight or  Robbie’s Marina  for a mix of local culture and wildlife encounters.

• Historical Landmarks : Including the Key West Lighthouse offers a glimpse into the maritime history of the Keys.
• Wildlife Interaction : A stop at Robbie’s Marina provides the opportunity for  tarpon feeding , a thrilling activity for wildlife enthusiasts.
• Water Sports : Incorporating locations like  Keys Cable  injects excitement with wakeboarding adventures, appealing to those seeking an adrenaline rush.

It’s advisable to consider travel time between destinations and book activities like wakeboarding in advance to ensure availability.

Tour Packages

Tour packages streamline the planning process by pre-selecting a combination of experiences tailored to diverse interests.

Tour operators typically arrange the logistics, including transportation and tickets, allowing visitors to enjoy a hassle-free adventure.

By choosing a strategy that resonates with their travel style, visitors can ensure their journey through the Florida Keys becomes a well-curated adventure.

Souvenirs and Shopping

The Florida Keys offer a treasure trove of unique souvenirs and shopping experiences that capture the essence of this tropical paradise. From charming boutiques on Duval Street to iconic Florida Keys keepsakes, shoppers can find a special memento to treasure long after their visit.

Unique Keepsakes

The Florida Keys are not only a destination for sun and relaxation but also a place where visitors can find distinctive souvenirs. The  Key West Hammock Company  is a notable spot where vacationers can purchase colorful hammocks, a practical yet decorative reminder of their time in the Keys.

The creatively named  Pelican Poop Shop  offers a variety of whimsical and island-themed gifts. Moreover, for lovers of sweet flavors, Key Lime products from local shops like  Kermit’s Key West Key Lime Shoppe  serve as a tasty and authentic keepsake to bring the taste of the Keys back home.

Shopping Destinations

Duval Street  in Key West is a hub for shoppers looking for a diverse shopping experience. Along this famed street, visitors will discover a mix of gift shops, galleries, and fashion boutiques. Here are a few notable stops:

• Conch Tour Train Depot : Souvenirs galore and a treat for those looking for a variety of memorabilia.
• Margaritaville Store : This store celebrates Jimmy Buffett’s laid-back island lifestyle, offering themed apparel, accessories, and of course, anything related to margaritas.

Furthermore, just south of Miami, the entire stretch of the Florida Keys is dotted with villages boasting unique shops and local art. One such place is  Casa Mar Village , where a once worn-down row of buildings has been transformed into a delightful array of gift shops and galleries that glisten under the Florida sun.

Things to Be Aware Of

Travelers should prioritize understanding the nuances of health, safety, and local regulations to ensure a seamless experience while exploring the Florida Keys.

Health and Safety

The Florida Keys are known for their warm, sunny weather with relatively low humidity, making for pleasant conditions year-round. However, sun protection is critical under the Florida sun. Visitors should consistently apply a broad-spectrum sunscreen and wear a hat and sunglasses.

It’s essential to stay hydrated and recognize the signs of heat-related illnesses, especially during outdoor activities or along the scenic drives on the Overseas Highway (US-1). The area has well-equipped medical facilities ready to assist with any health concerns.

Traveling along US-1, drivers must exercise caution. The highway, particularly famous for its stretch known as the Overseas Highway, connects the islands of the Florida Keys and often has only two lanes, which requires attentive driving. Mile Marker 0 is a famous endpoint in Key West, signifying the end of US-1 and a spot not to be missed for its celebratory signage, especially favored at sunset.

Local Regulations

Visitors should be aware of local regulations that aim to protect the unique environment of the Keys. Fishing regulations are strict, and one must be informed about the permissible sizes and species before engaging.

Parking regulations in popular areas like Key West are enforced, and tourists should pay close attention to signage to avoid fines. Lastly, various zones within the Keys might have specific speed limits to protect local wildlife, which also includes enforcement with cameras, especially as the road crosses many wildlife habitats along its route.

It’s advisable to keep a schedule that accommodates unplanned delays or detours, as the Overseas Highway, being the only main road, can experience frequent congestion, particularly during peak travel seasons or around notable viewpoints for sunsets.

Jerry Joyce

Jerry Joyce has been a Florida resident since 1988 and has lived in a variety of places in the South Florida area. Jerry is an avid boater & water sports enthusiast, beach aficionado, a lover of great food, muscle car fan and a theme park annual passholder for many years. Some of his favorite places in Florida include the Florida Keys, Walt Disney World, Cedar Key, the Loxahatchee River, St. Augustine and Ten Thousand islands.

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Florida Keys Travel Guide: Must-Read Tips for First Time Visitors

By: Author Leslie Harvey

Posted on Published: March 2, 2023

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When most travelers think of travel to the Florida Keys, a Jimmy Buffett song probably springs to mind. Lazy days, gorgeous white sand beaches, and colorful tropical drinks are definitely the stuff of a Keys vacation. Margaritaville indeed.

Despite its laid back vibe, a successful Florida Keys trip definitely requires a fair bit of planning. The learning curve for the Keys is surprisingly steep. There are a number of logistics to plan around to experience all the area has to offer, especially in a single visit.

My family spent a full week visiting the Florida Keys for a Thanksgiving vacation a few years ago. The Keys had been on our bucket list for awhile, but they are a long way from where we live in California. It took awhile to make a trip happen, and our plans to visit were delayed by the destruction wrought upon the Keys by Hurricane Irma in September 2017.

We learned a lot of tricks along the way and made a few mistakes, so I decided that a Florida keys travel guide for other newbies might be helpful to other travelers venturing to this destination for the first time too. Here is what other first time travelers – families as well as travelers without kids – to the Florida Keys need to know.

(Trips With Tykes uses affiliate links which means I may earn a small commission if you purchase through links in this post. See our full disclosure policy linked in the menu at the bottom of this site.)

Where are the Florida Keys?

I know the answer to this question may seem painfully obvious to many of you. When I was planning our own trip, however, I can’t tell you how many people I spoke to who didn’t really understand where the Keys were! Perhaps that’s because I live in California, and it’s not a place that many West Coasters are likely to visit.

Obviously, the Florida Keys are part of the state of Florida. They are an archipelago – a chain of islands – that start near the tip of Florida not far from Miami . The islands form a long curving arc south and west, dividing the Atlantic Ocean from the Gulf of Mexico. The southernmost inhabited island connected by road is Key West which is less than 100 miles from Cuba.

The famous Florida Keys “Overseas Highway” also known as Highway 1 connects the mainland to most of the inhabited Keys all the way to Key West. Highway 1 is one of the most popular drives on a Florida road trip , spanning 42 bridges.

Sub-Regions, Major Cities, & Layout of the Florida Keys

What many new visitors to the Florida Keys don’t understand is just how big of an area the Keys are. To drive all of Highway 1 from the mainland to Key West takes 2.5-3 hours. The Overseas Highway is mostly two lane, very dark at night, and highly trafficked during peak tourist periods. Don’t expect to seamlessly hop from one area to another without some effort.

If you plan to explore the entire region, you definitely need at least a week to do it justice. If you only have 2-3 days, I’d recommend picking a sub-region and sticking close to a single home base. Otherwise, you are simply going to be doing too much driving and missing out on the R&R that is the major reason to visit the area.

The Keys are comprised of many towns , roughly divided into the following three regions:

Upper Keys : Stretching from Key Largo into Islamorada, the Upper Keys is an area that can be most easily experienced as a day trip or weekend getaway from Miami and other South Florida destinations.

Middle Keys : The Middle Keys are separated from the Lower Keys by the famous 7 mile bridge and are decidedly less populated. My family stayed in this region, which was the area hardest hit by Hurricane Irma. The biggest city is Marathon, where there are a number of inexpensive but delicious restaurants and tour and dive operators.

Lower Keys : The lower keys start south of the 7 Mile Bridge in Big Pine Key. The hub of activity for the lower Keys is the city of Key West, the most inhabited city in the region.

What are the Best Airports for Flying to the Florida Keys?

Given their remote location at the very south of Florida, the Florida Keys aren’t within reasonable driving distance for many visitors. A lot of travelers need to fly in to experience a vacation there. The best airport choices for a Florida Keys trip are:

Key West International Airport (EYW) : Key West Airport is the only airport with commercial service located within the Florida Keys. The airport is just 15-20 minutes from the main tourist areas of Key West and is served by Delta, American Airlines, United, JetBlue , Allegiant, and Silver Airways. Flights are limited and often very pricey so this may not be a viable option for many travelers. That said, service to EYW has expanded the last few years, so check routes again anew in 2023 if it has been a few years since you’ve investigated flight options. If you do fly into this airport, Uber and Lyft are alive and well in Key West (although not always reliable elsewhere in the Keys). So it’s possible to go without a car if your plans will keep you in only Key West.

Miami International (MIA) : Many more visitors coming to visit the Keys start their trip at the major airport in Miami and rent a car to drive down the rest of the way. Miami to Key West is a 160 mile drive. Miami has a bit of a reputation for being a beast of an airport with long lines and challenging logistics (much like LAX and ATL), so be sure you leave plenty of time in your travel plans in both directions to deal with that.

Fort Lauderdale-Hollywood International Airport (FLL) : Another very viable option for travelers to the Keys is Fort Lauderdale. FLL is a larger airport with plenty of service from many cities and on multiple airlines (its largest carriers are Spirit and JetBlue and it’s also a Southwest Airlines mini-hub). It’s ultimately logistically easier than Miami even though its location adds about 30 extra minutes to the drive time down to the Keys. We used FLL for our trip and found the process quite seamless in terms of lines, rental cars, and more.

What do I Need to Know about Visiting the Florida Keys by Cruise Ship?

A lot of visitors to the Keys arrive via cruise ship. In fact, that was how I visited myself for the first time pre-kids. Cruise ships dock exclusively in Key West, so you really will only have a chance to explore the city proper if you come in via ship. The three Key West cruise ship piers (Mallory Square, Pier B, and Outer Mile) are all highly walkable to most of the major attractions in Key West. It’s a very easy cruise port to navigate for anyone, but especially for families.

Even if you aren’t coming in via cruise ship, it’s smart to keep an eye on the cruise ship schedules into Key West. They can dramatically affect crowd levels. If you want to have a mellower experience on a Key West day, try to visit on a day when ships aren’t in port (hard to do in the winter high season but easier to do in spring/summer/fall). The check out the cruise calendar several months in advance here .

Are the Florida Keys a Good Destination to Visit with Kids?

Yes! The Florida Keys is an ideal family vacation destination. My family found a ton of kid-friendly things to do on our week there – so much so that we didn’t feel like we had enough time. We spent most of our time in the middle Keys where our resort ( Hawks Cay Resort ) was located, taking a day trip down to Key West to experience all the city had to offer there. We didn’t even get to see much of the Upper Keys and Key Largo in the time we had.

One thing to be aware of – Key West after dark definitely has its bachelor and bachelorette party adult party vibes. And some of the fanciest resorts of the Central Keys are definitely more couples getaway destinations. But the vast majority of things to do and see in the Keys are incredibly family-friendly. Just pick your home base carefully.

How Has Hurricane Irma Affected the Keys?

Hurricane Irma made a direct hit on the Florida Keys in September 2017, which understandably has dramatically reshaped the landscape and tourism to the Keys since. Key West mostly escaped without major damage, but the Middle Keys were especially hard hit. Many of the homes and resorts there were completely destroyed.

Rebuilding took a very long time, made all the more difficult by the fact that a large percentage of the labor force left the Keys in the immediate wake of the hurricane. The tourism industry took another blow during the pandemic closures of 2020. Many businesses closed during this period and the labor market was impacted yet again.

Thankfully, the area has emerged from this one-two punch stronger than ever. Interest in the Florida Keys has only grown, and the area is bustling once again. That said, demand sometimes exceed supply. This means prices are higher than ever, even while some business operators (resorts, restaurants, etc.) are still short staffed.

Visitors should be aware of these challenges, especially when combined with the fact that the Keys are very much already on island time. If you can embrace your inner Jimmy Buffett, you will likely have a blast. But if you demand impeccable luxury hotel level service, it’s going to be harder to be satisfied, even at resorts charging luxury level prices.

Best Things to Do in the Florida Keys

Because we were only in the area for a week, we didn’t even begin to comprehensively do everything the Keys have to offer. Here are the top activity highlights that we enjoyed that I’d recommend to other visitors:

Conch Train (Key West)

It’s touristy and expensive, but it’s worth it. The Conch train is a vehicle that takes you to various sites all around Key West, from the Ernest Hemingway Museum to the Southernmost Point of the United States. Guides share a bit of history and humor as you see the city’s most famous stops. You can ride it multiple times and hop on and off so you may be able to use it as both transportation and as an attraction.

Snorkeling & Scuba Diving (Multiple Locations)

My husband and I both scuba dive and we didn’t want to leave the Keys without seeing beneath the surface. We found a dive operator that let us take turns diving while the other of us stayed on the surface and snorkeled with the kids.

The amazing scuba operator we used sadly shuttered its doors for good, but there are a number of top notch dive operators all over the Keys. Some of the top snorkeling spots include: John Pennekamp Coral Reef State Park in Key Largo, Sombrero Reef near Marathon (where we dove), right off the beach in Key West at Fort Zachary Taylor Historic State Park, or in the Dry Tortugas.

If you have younger kids not ready to snorkel, consider doing a glass bottom boat tour as an alternative way to view marine life.

Morada Bay Beach Cafe (Islamorada)

This restaurant on the beach is affiliated with the resort where Netflix’s Bloodline was filmed, so my husband and I had to do a date night there. It’s kid-friendly as well, so feel free to bring the whole family. If you plan to have dinner there, arrive well before sunset to grab a table with a view. The fresh seafood is to die for and definitely don’t miss the Key Lime pie.

Mallory Square Sunset Celebration (Key West)

Every evening before sunset, street performers flock to Mallory Square in Key West and perform for the crowds right as the cruise ships are boarding for the evening.

Lagerheads Beach Bar (Key West)

While we were in Key West, we headed to Lagerheads for lunch. This open air restaurant is little more than a beach shack, but what makes it fun for families are the tables on the beach. Our kids played in the sand and surf with other kids while my husband and I enjoyed a margarita!

For even more in-depth recommendations of what to do (especially with kids) in the Florida Keys and all over the state of Florida, check out these guides from some fellow travel bloggers I personally know and trust:

• 26 Things to Do in Key West from Crazy Family Adventure
• 29 Perfect Things to Do in Key West for Every Type of Traveler  from 365 Atlanta Traveler
• 49 Things to do in Florida from 365 Atlanta Traveler
• Planning a Florida Keys Road Trip from We3Travel
• Key West Girls Trip from Your Time to Fly

Tips & Tricks for First Time Visitors to the Florida Keys

Here are few additional tips and tricks we picked up in our Keys travel:

• Plan for cell dead spots : You are in the middle of an ocean. It might not surprise you that cell coverage can be spotty in various places in the Keys. Input directions into your cell phone before you leave the WiFi at your resort. (Maps in a guidebook can come in handy too!)
• Really do your resort research : Given the volatility of the last several years, be sure the Keys resort you book is ready to deliver the travel experience you seek. Read recent reviews on sites like TripAdvisor that can really give you a sense of the situation on the ground at a given time.
• Pre-book excursions : Because of increased interest in the Keys, a lot of tour operators have more demand than they have employees. If you want to scuba dive, snorkel, or do other similar excursions, I highly recommend booking ahead. If you wait to call until you get to the Keys, you may find many activities fully booked.
• Have a parking strategy for Key West : Parking in the main part of Key West is a bit of a beast (and is pricey). If you are headed to the many attractions in Mallory Square on a day trip from elsewhere in the Keys, I recommend parking once and then using Uber or Lyft or the Conch Train to get around.
• Combine the Keys with an Everglades trip : If you are flying into Miami or Fort Lauderdale, a Florida Keys trip can really be combined with a few other destinations. We decided to stay one night in Fort Lauderdale and spend the better part of a day in Everglades National Park before driving down to the Keys. It was a huge hit with both the kids and adults in our family – who can resist seeing alligators up close? (If you are new to national parks travel, check out my beginners guide to visiting national parks and be sure to know how to get a free national park pass if you have a 4th grader in the family!)

Disclosure : This post was originally published in partnership with by Moon Travel Guides. It has been updated independent of that relationship since that time. Check out Moon’s Florida Keys guidebook for more. As always, all opinions are my own.

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Saturday 10th of December 2022

I just got back from the keys. Went all the way down to Key West. It was in November and was very beautiful. I would tell anyone that they should see it at least one. Love it.❤️

Monday 7th of February 2022

Thanks for the wonderful info. Our family will be in the Keys for a week in April. Looking for the best places to snorkel in the Keys. What Key has the best chance of seeing fish and healthy reefs? What company does a good job with kids 10 and 12, and a family of 7? We are staying in Key Largo. Marathon, Key West, and Homestead. Thank you again.

Tuesday 4th of May 2021

Is the weather still warm and able to swim in the ocean during Thanksgiving time?

Thursday 14th of January 2021

Thank you so much for sharing this. We have a trip with my family next week on Florida and I’m going to visit there. Thank you so much. You are the best!

Wednesday 9th of December 2020

Anyone have any nanny recommendations in the Keys? Thank you!

Ultimate Florida Keys Travel Guide (+ A Map of the Florida Keys)

Wondering how to plan a trip to the famous Florida Keys ? With its crystal clear water, delicious seafood, and a multitude of activities, the Florida Keys are a must-visit destination in the USA!

The Florida Keys are truly my happy place, and I want everyone to experience them too. I was lucky enough to grow up visiting the Keys. My dad is from Islamorada (part of the Upper Keys), so he made sure we visited a lot and experienced all the Keys have to offer. And they have A LOT to offer!!!

From Key Largo to Key West , there are so many incredible hotels, restaurants, and activities to experience in the Keys. In this post, I cover everything you need to know about visiting the Florida Keys , including the best time to visit, places to stay, where to eat, and the top activities in each major Key.

Plus, I’ve put together a complete map of the Florida Keys with all of the highlights! So keep reading to help plan your perfect trip to the Keys!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you!

The Ultimate Florida Keys Travel Guide (+ A Detailed Map of the Best Spots)

Complete florida keys map.

If you’ve never been to the Keys, it’s important to know the Florida Keys are not just Key West . The Florida Keys are actually made up of over 200 islands! Of course, not all of these are inhabited, but there are still quite a few Keys to choose from.

Make sure to check out my blog post How Many Keys Are in the Florida Keys? for more FL Keys fun facts!

To help you plan your trip, this travel guide breaks down the Keys into three main areas: The Upper Keys, The Middle Keys, and The Lower Keys . For each area, you’ll find a mini guide, including where to stay, where to eat, and things to do!

I’ve also put together a Florida Keys map that includes all of my favorite stops throughout the Keys, including restaurants, hotels, shops, breweries, and more! Make sure to save this map of the Florida Keys before your trip!

Best Time to Visit the Florida Keys

In my opinion, there is no “bad” time to visit the Keys.. You can pretty much guarantee that it’ll be warm year round, as is the norm in southern Florida! However, there are a few different things to consider when planning your trip to the Keys depending on the time of year.

For a detailed breakdown on when to visit the Keys, including a list of seasonal events, make sure to check out my full guide: Best Time To Visit The Florida Keys !

Winter is the “high” season in the Keys. Snowbirds flock to Florida to escape the brutal winter weather up north – which means busy restaurants, higher hotel rates, etc.. While cold fronts can happen, it’s uncommon for the temperature to drop below 55 degrees in the Keys.

So even though it’s winter, you can still partake in the standard Florida Keys activities. The ocean might be a little chilly (but not unbearable), and there are always wet suits if needed! Overall, plan for crowds and inflated costs if you’re visiting in the winter months, but gorgeous weather!

Spring is personally my favorite time to visit the Keys. The winter crowds start to die down around late February, and the weather starts to warm up, with highs in the upper 70s and lows in the 60s. Plus, blue skies are the norm during this time, with very low precipitation rates.

The only downside of visiting the Keys in March/April is the possibility of spring break crowds. This will be most noticeable in Key West, but if you’re going to Key West to have peace and quiet, I’d re-think your plans..

No matter what, the Keys are extremely enjoyable in the Spring and a perfect time of year to visit!

As temperatures rise in June and July, the crowds decrease, along with hotel prices. Most people avoid the Keys in the summer because, let’s face it, Florida summers can be brutal . The mosquitos come out. It rains every afternoon. It’s HOT.

As a Floridian, this is the norm for me, so I don’t avoid the Keys in the summer by any means. In fact, it’s a good time to visit if that type of weather doesn’t bother you, because hotels are cheaper and there’s way less people!

We used to visit the Keys every July 4th and it was still incredible.. but if you’re not a fan of 90 degree weather, I would plan to visit during another time of year!

The biggest thing to consider when planning a trip to the Keys in the fall is hurricane season , which runs from June – November . However, the peak of the season is August & September. During this timeframe, expect hot days and frequent rainfall in the afternoons.

If you’re planning a trip to the Keys during hurricane season, plan for the worst and make sure everything is refundable . Hurricanes can pop up out of nowhere and lead to canceling your vacation within a week’s notice (or less!)

How to Get to the Florida Keys

So, you’ve picked a time of year to visit.. Now let’s talk about how you will get to the Florida Keys! How you arrive in the Keys will depend on a few factors, including your budget, your timeframe, and your departure city.

For example, if you live in Florida, you can probably drive to the Keys , unless you live in North Florida, which would be a long adventure! If you’re traveling from any other state, you are probably going to be flying in.

Flying to the Florida Keys

Flying into key west.

You have a couple different options for flights to the Florida Keys. If you’re traveling to Key West and only Key West, you can fly directly into Key West International Airport (EYW) . Some US cities even have direct flights to Key West, like Asheville, New York City, Tampa, and Indianapolis. Check out the flight prices below!

Flying into Fort Lauderdale or Miami

If you are planning to visit other Keys besides Key West, don’t limit yourself to the Key West airport only, because it can get expensive!

I recommend flying into Fort Lauderdale airport (FLL) or Miami airport (MIA) and then renting a car and driving down to the Keys. If you’re staying in one of the Upper Keys, driving from these airports will be relatively painless (only 1-2 hours depending on which you choose)!

If you want to go all the way to Key West, and flights to Key West airport are super expensive, it is totally doable to drive to Key West from Fort Lauderdale or Miami airport! The drive from Miami to Key West takes less than 4 hours, and there are plenty of places to stop along the way to break up the drive! In fact, I highly recommend it 🙂

You can also consider booking one way flights: one into Miami/Fort Lauderdale and one out of Key West. This way, you only have to do the drive through the Keys one time!

Renting a Car in the Florida Keys

As mentioned above, if you plan on visiting multiple Keys, you’ll need to rent a car ! You can pick up a rental car from any of the 3 airports mentioned above.

I highly recommend  RentalCars.com . They allow you to compare prices across all of the major rental car companies. Plus, they have a great cancellation policy (typically free cancellation up to 48 hours in advance). Oh, and they price match!

For your trip to the Florida Keys, I recommend getting a car with good fuel economy to save money! If you are driving up and down the length of the Overseas Highway, that’s over 300 miles! With gas prices the way they are, you are going to want to save where you can!

TIP: Avoid arriving for your trip on a Friday afternoon if flying into Fort Lauderdale or Miami. Not only will you hit rush hour traffic in Miami, but you will also hit traffic getting into the Keys. There is only one main road in and out of the Keys, and it can get backed up quickly!

Florida Keys by Boat

So we covered air and land.. another option for visiting the Keys is by sea! A lot of South Floridians take their own boats down to the Keys. Of course, if you’re traveling from out of state or don’t have a boat, this isn’t an option, but a cruise is!

Many cruise lines include a stop in Key West on their Western or Eastern Caribbean cruises. You can cruise from New Orleans, Galveston, Mobile, or other parts of Florida.

However, I really think you have to spend more than just a day in Key West to truly appreciate the beauty of the Keys! That’s why I highlight all the different areas in this Florida Keys Travel Guide, not just Key West!

Where to Stay in the Florida Keys

Below I will breakdown the main 3 areas of the Keys and provide hotel recommendations for each area based on different budgets! However, I wanted to note that you are not limited to just hotels in the Keys.

Vacation rentals are very common in the Keys! You can check out options on VRBO or Airbnb . It’s worth noting that some parts of the Keys do not allow vacation rentals for less than a 28-day stay, so depending on the area, options might be limited. 

Looking for something unique? Consider renting out a sailboat or houseboat to stay on!

If you decide to go the hotel route, there are tons of options, from seaside motels to luxurious resorts. In each section below, I’ll give some hotel recommendations for each area of the Florida Keys!

The Upper Keys

The two main towns that make up the Upper Keys are Key Largo and Islamorada . Key Largo will be your first stop on your journey south through the Keys, followed shortly by Islamorada.

The Upper Keys are very popular among Floridians due to their proximity to the rest of the state. In fact, many people from south Florida often do a Miami to Key Largo road trip , since the drive only takes an hour!

In addition, the Upper Keys have some of the best snorkeling and scuba diving, thanks to the Florida  Keys  National Marine Sanctuary , so it’s a very popular area for boaters. (Make sure to check out my Key Largo Snorkeling Guide and my Islamorada Snorkeling Guide for more info!

What Is There to Do in the Upper Keys?

My favorite part of the Upper Keys is there is SO much to see and do. I have a list of Free Things to Do in Key Largo and Things to Do in Islamorada , but here’s a quick overview of both!

• John Pennekamp Coral Reef State Park (the first undersea park in the United States!)
• Sunset cruise in Key Largo (full guide here !)
• Snorkeling at Alligator Reef Lighthouse
• Islamorada Beer Company
• Dolphins Plus Encounter
• Sports Fishing Charter
• Feed The Tarpon At Robbie’s
• Kayaking In The Bay
• Have a Rum Runner at the Tiki Bar

Where Should I Stay in the Upper Keys?

All of my favorite Florida Keys hotels are located in the Upper Keys! If you’re on a budget, you can’t go wrong with Drop Anchor Resort or La Jolla Resort .

If you have a moderate budget, my absolute favorite resorts are the Islander Resort and Postcard Inn !

For luxury travelers, you can’t go wrong with The Caribbean Resort or Playa Largo Resort !

For more suggestions, make sure to check out my detailed guides on the Best Hotels in Key Largo and the Best Hotels in Islamorada !

Where Should I Eat in the upper Keys?

There’s no shortage of incredible restaurants in the Upper Keys. Islamorada is the sports fishing capital of the world, so the seafood here is unbelievable. In fact, not one but TWO restaurants in Islamorada have been featured on Diners, Drive-Ins, and Dives!

Luckily, I’ve put together two full guides on this exact category: the Best Restaurants in Islamorada and the Top 10 Key Largo Restaurants !

The Middle Keys

Next up are the Middle Keys.. a little bit further south and a little less people than Key Largo or Islamorada. Marathon is the heart of the Middle Keys and encompasses many little keys within its limits. There is also Duck Key, home to the famous and luxurious resort, Hawk’s Cay!

What Is There to Do in the Middle keys?

There is a ton to do in the Middle Keys, especially for younger children and those who love getting outdoors. The Middle Keys are also home to the Seven Mile Bridge , one of the longest bridges in the world!

• The Turtle Hospital
• Dolphin Research Center
• Sombrero Beach & Reef
• Bahia Honda State Park
• Seven Mile Bridge
• Crane Point Nature Center

Where Should I Stay in the Middle Keys?

There are quite a few hotels and VRBOs to stay in in the Middle Keys. In my opinion, none as great as in the Upper Keys, but still some wonderful hotels! For budget travelers, check out the Rainbow Bend Resort . Other options that are a little higher priced are Isla Bella Beach Resort and Faro Blanco Resort .

For luxury travelers, there’s really nothing better than Hawk’s Cay Resort . This resort takes up an entire Key itself (Duck Key), and it does not disappoint! It has its own lagoon, dolphin sanctuary, and more!

The Lower Keys

Last but definitely not least.. let’s talk about the Lower Keys – the highlight of which is Key West! Key West truly has something for everyone to enjoy.. beaches (rare for the Keys), bars, museums, shops, gardens, and more.

For this reason, Key West is extremely popular for families, spring breakers, snow birds, and more. You can arrive by cruise ship, flight or car (reference the beginning of this travel guide!)

Aside from Key West, there’s also Big Pine Key and No Name Key, which are perfect for that off-the-beaten-path feel. If you’re looking for a real adventure, make sure to visit Dry Tortugas National Park , which is located on  a small archipelago about 70 miles from Key West!  

What Is There to Do in the Lower keys?

Most people think Key West is just bars, but there is plenty of other things to do! In fact, I wrote a list of 10 FREE Things to Do in Key West AND 25 Epic Things To Do in Key West , but here’s a quick overview!

• Duval Bar Crawl
• Mallory Square
• Sunset Cruise (read my full guide here !)
• Southernmost Point of the Continental United States
• No Name Pub
• Key Deer Refuge
• Dry Tortugas National Park
• Sunset Key 
• Ernest Hemingway Home

Where Should I Stay in the Lower Keys?

The range of places to stay in the Lower Keys is extremely impressive! If you want to be within walking distance of the main sites in Key West, you’ll need to stay in Old Town . There are TONS of small BnBs and vacation house rentals in this area.

The hotels in Old Town, like Ocean Key Resort and the Mansion on the Sea sell out quickly but are worth the cost! If you’re looking for the ultimate luxury, Casa Marina Resort is a beautiful property right on the beach!

However, don’t rule out Old Town if you are visiting Key West and are looking for a more traditional hotel experiences. Places like the Hilton Garden Inn and Margaritaville Beach House are very nice hotels and are more reasonably priced than the fancy hotels in Old Town! Plus, most New Town hotels have free shuttles to Old Town.

P.S. If you can only visit ONE Key and can’t decide which one to choose, make sure to check out my guide comparing Key Largo vs Key West !

Where Should I Eat in the Lower Keys?

One of the best parts about visiting the Lower Keys is the amount of incredible restaurants! For breakfast or brunch, you have to go to the famous Blue Heaven . Make sure to get a giant slice of key lime pie!

For a one of kind experience, make a reservation at Latitudes , a decadent restaurant located on Sunset Key.

My other favorite spots around town are Hot Tin Roof , Santiago’s Bodega , and Black Fin Bistro !

Packing Essentials for the Florida Keys

Your packing list for a trip to the Florida Keys will be very similar year-round, as there’s no harsh winters here! For most of the year, you can get away with shorts, tshirts, and flip flops.. what a life right?!

There are some essentials, however, that I recommend for your trip to the Keys, whether you’re visiting in the summer, the winter, or somewhere in between!

Make sure to check out my guide on What to Wear in Key West for even more details!

1. Sunscreen : I will scream this from the mountain tops until I am blue in the face! If you are going to be outside, you need to wear sunscreen. I highly recommend Supergoop! Their unseen suncreen is amazing!

2. Snorkel Gear : If you have your own gear, I highly recommend bringing it on your trip to the Keys!

3. Underwater Phone Pouch : An underwater case for your phone like this one is perfect for capturing photo and video of all the incredible coral and wildlife you will see when snorkeling!

4. Polarized Sunglasses / Hat : To protect yourself while you’re in the sun and out on the water! Polarized glasses will also help cut the glare on the ocean so you can see the wildlife! I love this inexpensive two pack from Amazon! 

5. Water Shoes : Okay by water shoes, I mean shoes that can get wet! not those dorky tourist shoes…lol! I have these Reef sandals that are totally waterproof and are great for outdoor adventures like kayaking, taking on a snorkel boat, etc. 

Final Thoughts

As you can see, the Florida Keys are an epic vacation destination for all types of travelers. On this famous island chain, you’ll find world-class restaurants, hotels, and activities, plus gorgeous weather year round!

Whether its catching fresh fish in Islamorada, camping under the stars in Bahia Honda State Park, or partying the night away in Key West, – there is truly something for everyone in this slice of paradise!

Don’t forget to pin this post for future planning!

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How to Take the Ultimate Florida Keys Road Trip

The best beach bars, hotels, restaurants, and places to visit on a drive down Florida’s Overseas Highway from Key Largo to Key West.

A drive down Florida's Overseas Highway from Key Largo to Key West offers the perfect blend of eccentric bohemia and chic joie de vivre . As the mile markers decrease, Old Florida charm sharpens into focus. Strip malls hawking beach sundries and snorkeling tours along the upper reaches of U.S. 1 give way to dazzling turquoise flashes as the road becomes more bridge than highway. The route south is festooned with the Keys' ubiquitous kitsch — a giant, spiny lobster presides over a local arts village, lipsticked manatees clutch mailboxes, and hand painted mermaids tempt passersby with the promise of sunset cocktails.

You could drive the 113-mile stretch in a little over three hours, but why would you want to? Road trips , especially one as iconic as this, are all about the stops along the way. So put the top down and cue Jimmy Buffet. Here's our guide to the best the Florida Keys has to offer.

Ease yourself into the Keys' laidback vibe just south of Homestead with a detour onto Card Sound Road. A stop into Alabama Jack's is a must, especially if you're a first-timer. The scrappy, waterside seafood shack has been the Keys' unofficial welcome wagon since 1947 and serves some of the best conch fritters around. Live music and the line of Harleys outside add to the honky-tonk scene.

With your internal clock synced to island time, cruise over Card Sound Bridge and into Key Largo where you'll find John Pennekamp Coral Reef State Park at mile marker 102.5. Explore the park's prolific marine life and a portion of the 360-mile Florida Reef Tract — North America's only living coral barrier reef — on a guided snorkeling tour . Or rent kayaks and head out for a paddle through miles of mangrove-lined wilderness trails.

Key Largo is at the epicenter of sustainability efforts in the Florida Keys, especially when it comes to reef health. At the Coral Restoration Foundation , researchers are rearing and planting corals in undersea nurseries. For a unique experience, snorkelers and divers looking to add an eco-tourism stint to their travels can assist scientists with outplanting and reef monitoring at active restorations sites.

After a day of sea and sun, check into the breezy Baker's Cay Resort , a lush retreat tucked into a secluded setting with gorgeous Florida Strait views. The resort partners with local environmental organizations to create eco-friendly guest programming. It was also the first resort in the Keys to join Reef Relief's " Skip the Straw " campaign.

You could easily spend a few days hopping around the string of tiny islands that make up Islamorada and while you do, The Moorings Village is the perfect place to call home.

Built on a former coconut plantation, the resort is home to eight private cottages nestled amidst tropical landscaping just steps from the Atlantic. Eight-hundred palm trees dot the property, and there's no shortage of hammocks for lounging beneath the verdant fronds.

Grab a paddleboard and head out for an ocean jaunt, watch the world go by from the cool shade of your porch, or while away a few hours by the gorgeous pool. If you can tear yourself away, single-speed beach cruisers are available for a pedal around town. Check out the galleries around the corner in the Morada Bay Arts and Cultural District — every third Thursday is the district's evening art walk — or pop into the beer garden at the Florida Keys Brewing Company for a hyper-local tasting flight.

Robbie's Marina , one of the Florida Keys' most iconic landmarks, sits on the tip of Lower Matecumbe Key, about five miles south at mile marker 77.5. The epitome of the archipelago's barefoot affability, Robbie's is a waterside shantytown of sorts that includes an outdoor marketplace, a marine sports outpost, and the Hungry Tarpon restaurant, named for the school of enormous silver fish that have been circling the docks for decades. Seven bucks will get you a bucket of bait and admission to the dock, and feeding the leaping, thrashing creatures provides a memorable diversion.

Afterwards, head out for an eco-tour through Islamorada's pristine waters with Captain Sam Zeher or just chill dockside with one of Robbie's Trailer Trash Bloody Marys, complete with a beef-jerky straw.

When the dinner hour beckons, shake the sand from your toes and head to Pierre's , an elegant plantation-style house with a wide verandah overlooking Florida Bay. A few miles north at Marker 88 , the chef serves the kind of super-fresh seafood one would expect to find in the sportfishing capital of the world. Tuck into cracked coconut-crusted shrimp and fresh Florida lobster on the outdoor patio with a glass of fruity Chardonnay — for a relaxed joint, Marker 88 has an excellent wine list. At either spot, the famous Keys sunset is guaranteed to put on a memorable show.

Even before Hemingway's old man took to the sea, the Keys were a saltwater angler's paradise, legendary for big game like sailfish, wahoo, and blue marlin. Though pulling a trophy fish from the ocean can be a thrill, sometimes the best part of casting a line is eating your catch later.

One of the best ways to do so is on a hook-and-cook adventure at Hawks Cay Resort on Duck Key, a pocket-sized island about 20 miles south of Islamorada. When it comes to relaxation, the resort offers a stunning adults-only enclave called Oasis Cay.

Get out onto the water with lifelong conch (i.e., Florida Keys native) Captain Dave Perry , who has been fishing the Keys for decades and runs charters out of the Hawks Cay Marina with Captain Justin Brunk. In addition to blue water hunting, the two specialize in fishing the reef for snapper and grouper, fish that can later be blackened, grilled, or fried for a hyper-local meal at Angler and Ale , the resort's dockside restaurant.

Connecting Marathon to the Lower Keys, the Seven-Mile Bridge is a highlight of any Keys road trip and driving it feels like being immersed in an ocean-themed movie. But before you do, take a ferry out to picturesque Pigeon Key for a dose of Keys history.

In the early 1900s, Florida tycoon Henry Flagler envisioned an Overseas Railroad linking mainland Florida to Key West. The project was nicknamed Flagler's Folly — no one believed his ambitious plan would come to fruition — yet, despite naysayers, the rail line was finished in 1912 complete with the engineering marvel that became the Seven-Mile Bridge. During the railroad's construction, more than 400 workers lived on Pigeon Key, which is now listed on the National Historic Register. Tours of the tiny island leave three times daily from the Pigeon Key Visitor's Center and offer a deep dive into the story of the railroad, its ill-fated demise, and the scenic highway travelers drive today.

The Lower Keys

Take a detour for some beach bliss at Bahia Honda State Park , a 524-acre swath of nature tucked between the Atlantic and the Gulf. Don't forget to drop by Sandspur Beach, long considered one of the best in the Keys.

On Big Pine Key, stop into the new Florida Keys National Wildlife Refuges Nature Center, which features exhibits spotlighting the Keys' four wildlife refuges including the nearby National Key Deer Refuge . Established in 1957, the refuge protects approximately 9,200 acres of land on Big Pine and No Name Keys that serves as habitat for endangered Key Deer. Stick to the speed limit around here — the diminutive creatures have been known to dart into the road, especially at dawn and dusk.

About 30 minutes south, you'll find authentic, Old Keys spirit on the docks of Geiger Key Marina at The Fish Camp . Founded by local restaurateurs Michelle and Bobby Mongelli, also behind the well-loved Hogfish Bar and Grill on nearby Stock Island, this open-air tiki bar and seafood joint claims to be on "the back side of paradise," which certainly feels accurate when you're sitting waterside with a plate of succulent Key West pink shrimp and a cold beer. The Sunday afternoon barbecue is legendary.

Head out to explore the labyrinth of waterways around Stock Island on a guided kayak tour with Lazy Dog Adventures . Trips leave from a tiny inlet on Cow Key Channel and wind through the mangrove tunnels and saltwater creeks hugging the edge of the Atlantic. The vibrant ecosystem provides a habitat for manatees, sea stars, tropical fish, and all kinds of shorebirds — many of which you'll encounter while paddling through the Keys' backcountry wilderness.

Key West exudes the same anything-goes bonhomie it did back in the day of rumrunners and speakeasies — only now it's infused with a shot of modern flair. Colorful conch cottages line the streets of Old Town, swank cocktail salons mingle with celebrated watering holes on Duval, and feral fowl give new meaning to free-range as they strut along the sidewalks crowing with carefree abandon. It also has an eclectic mix of top-rated hotels to suit every traveler.

Find respite from the downtown bacchanalia at the Parrot Key Hotel and Villas . The entire property breathes Old Key West charm. Walkways edged with white-picket fences wind through tropical gardens past hidden swimming pools and quaint, two-story clapboard bungalows. Bright-blue Adirondack chairs sit on covered porches, hammocks swing beneath shady palms, and ceiling fans spin lazily overhead at The Grove, the resort's new open-air restaurant. Parrot Key's complimentary shuttle delivers guests throughout the day to either a private beach club at Smathers Beach or to the heart of Old Town. For a DIY adventure, a fleet of single-speed beach cruisers invites exploration.

At four miles long and two miles wide, Key West is made for biking. Pedal through dappled sunlight along Whitehead Street to the Ernest Hemingway Home and Museum . Inside, passionate docents supply a glimpse into the profound yet tragic genius of one of the Lost Generation's most colorful characters. Pay further tribute to Papa at the Hemingway Rum Company , which produces the award-winning Papa's Pilar, named for the author's beloved fishing boat. The company's flagship headquarters, housed in a former tobacco warehouse, is part distillery, part tasting room, and part museum. Find a spot at the bar and sample delicious, dark and blonde Solera-blended rums amidst all variety of Hemingway-themed ephemera.

When the sun starts to set, climb aboard Danger Charters ' elegant, three-masted schooner for a wine-tasting sail that offers a polished alternative to the nightly circus — think fire juggling acrobats and hoop-jumping cats — at Mallory Square. Or take a quick jaunt on the private ferry to Sunset Key for a gastronomical adventure overlooking the Gulf of Mexico at Latitudes , the signature restaurant at Sunset Key Cottages . There, you'll dine on yellowtail, grouper, or cobia by the light of tiki torches with your toes in the sand. Innovative cocktails, crisp white tablecloths, and dreamy island views round out a memorable evening.

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The Perfect 5 Day Florida Keys Itinerary for First Timers

In this article, I’m sharing the perfect 5 day Florida Keys itinerary, ideal for first time visitors. The Florida Keys are a pretty epic American road trip destination. You’ll find yourself driving along an overseas highway, hopping between different tropical islands.

I’m basing this itinerary off my most recent trip to the Florida Keys, in which I road tripped from Miami Airport to Key West and back again with my friend Mary, exploring multiple keys along the way.

Highlights of this 5 day Florida Keys itinerary include:

• Snorkeling in the USA’s first underseas park
• Key lime pie… lots of key lime pie
• Beach resorts and bed & breakfasts
• Fishing (and then eating your fish for dinner!)
• Sunset sailing
• Exploring a tropical fruit grove
• Driving the Seven Mile Bridge
• Touring a sea turtle hospital
• Visiting Key West classics like the Ernest Hemingway House

Let’s get to it.

5 Day Florida Keys Itinerary: An Introduction

This 5 day itinerary is designed for first time visitors to the Florida Keys to give you an overview to each of the main keys. Maybe you have been to Key West before, but this is your first time exploring the keys as a whole.

Did you know that the Florida Keys are made up of about 1,700 islands, all connected by a 113-mile overseas highway? Yep, you’ll be road tripping over water in this epic itinerary.

This 5 Day Florida Keys Road Trip Itinerary:

Miami > Key Largo > Islamorada > Key West > Marathon > Miami

How Many Days Do You Need in the Florida Keys?

In my experience, five days is the minimum amount of time required to road trip the Florida Keys, if you’re planning to visit more than just Key West.

Below I’m sharing the ideal Florida Keys itinerary for first timers, spread across five full days. Note that I say five full days, because this itinerary does involve travel in and out of Miami Airport on days 0 and 6.

Here is a quick day-by-day breakdown of my recommended way to spend 5 days in the Florida Keys:

• Day 0 : Fly into Miami
• Day 1: Miami > Islamorada
• Day 2: Islamorada
• Day 3: Islamorada > Key West

Day 4: Key West

• Day 5: Key West > Marathon
• Final Day: Marathon > Miami

You can read my itinerary in much more detail below. I’ve designed the itinerary with general activity lists, rather than restricting you hour-by-hour, because I think that’s more helpful (and digestible, as a reader!).

Let’s get to it!

Car Rental for a Florida Keys Road Trip

You’ll need to rent a car for this Florida Keys road trip, unless you live in Florida or are driving down!

Reserve your rental car at least a few weeks in advance, to avoid any car shortages. Then, pick it up at the rental car counter at Miami Airport.

I recommend Discover Cars for car rental in the Florida Keys, because they show you the best deal from many different companies. You can filter by your personal preferences, such as size of car or insurance level.

Day 0: Fly to Miami

Highlights: Arrival to Miami, pick up rental car.

Your task for “day zero” is just to fly into Miami (or Fort Lauderdale) and pick up your rental car. Of course, you could do this early on your first full day instead, but personally I enjoyed doing this the night before so we had a fresh start for our road trip in the morning!

Where to Stay

Stay somewhere close to the Miami Airport. We stayed at the AC Hotel Miami Airport West for one night and I recommend it. It was a quick drive from the Miami Airport, and the hotel itself was sooo nice and comfortable with some high tech amenities.

Where to Eat

Have a quick dinner. For your first night, I recommend you just grab a quick meal before the adventure starts tomorrow.

Mary and I actually popped by Chipotle for takeout, which we ate in our room at the AC Hotel!

Doral City Place is another option very close to the AC Hotel Miami Airport West. It’s a large shopping center with lots of restaurants.

Fly into Miami. Obviously!

Pick up your rental car. This took us a surprisingly long time (1 hour) with the lines at the car rental station, so be sure to account for that possibility.

Relax in hotel. Mary and I actually ended up watching The African Queen (which we were able to play via Youtube on the massive TV in our AC hotel room ). This was as “research” for our steamboat ride on day 1 – read about that below!

Day 1: Miami to Key Largo to Islamorada

Highlights: A steamboat tour, fisheries lunch, check into beach resort.

Drive time: 2 hours

The first full day of your 5 day Florida Keys itinerary is all about the upper keys. You’ll spend the day driving from Miami down to your beach resort in Islamorada, which takes about 2 hours in total with some fun stops along the way in Key Largo (the northernmost key).

Day 1 | Miami to Key Largo to Islamorada:

• Check out of AC Hotel Miami Airport West
• Drive to Key Largo (~1.5 hours)
• 10am pre-booked steamboat tour on The African Queen
• Lunch at Key Largo Fisheries and Backyard Cafe
• Key lime pie at Keys Chocolate and Ice Cream
• Drive to Islamorada (~30 minutes)
• Check in to Postcard Inn Beach Resort
• Dinner at Twisted Shrimp
• Cocktails and beach sunset at Postcard Inn

I recommend booking a beach resort in Islamorada. We stayed at Postcard Inn Beach Resort for two nights. This was a great central location for the two days of our itinerary that we spent exploring the upper keys.

Postcard Inn is special because it’s directly on the ocean, and guests have access to paddle boards, kayaks, bikes, and more.

Fun fact: this resort is also where the rum runner cocktail was invented! Obviously, we had to partake.

Book your stay at Postcard Inn here.

RELATED | Best Places to Stay in the Florida Keys (For All Budgets)

Lunch at Key Largo Fisheries (Key Largo). This is a very “keys” experience and perfect for lunchtime. Eat some super fresh fish or crab (or lobster!) and see the nurse sharks swimming off the dock.

Key lime pie at Keys Chocolate and Ice Cream (Key Largo). If you are like Mary and I, then you’ll obviously waste no time in getting your hands on some key lime pie.

I recommend stopping at Keys Chocolate and Ice Cream after lunch for their chocolate-covered key lime pie on a stick (and yes, it was gluten free!! Read my guide to finding gluten free key lime pie in the Florida Keys here ).

Dinner at Twisted Shrimp (Islamorada). A roadside seafood restaurant where you can actually eat IN a boat!

This place is extremely on brand for the keys.It’s laidback, family owned, and the (gluten free) fried shrimp is a delight. It is a great stop for dinner on your first night!

RELATED | Gluten Free Key West and the Florida Keys Guide

Cocktails at Postcard Inn’s Tiki Bar. You HAVE to visit the Tiki Bar for obvious reasons – this is reportedly where the rum runner cocktail was invented!

Go on The African Queen Steamboat Tour. Taking this historic steamboat tour is the highlight activity of the first day of your 5 day Florida Keys itinerary. This is literally THE boat that featured in the 1951 adventure film starring Humphrey Bogart and Katharine Hepburn. It’s actually on the U.S. National Register of Historic Places.

I recommend booking a tour for 10am, which is what we did. This was good timing as it gave us ample time to drive down from Miami, and we finished in time for lunch.

It was somewhat surreal sitting in this boat, cruising through the Key Largo canals and out to the ocean and back, after just having watched the movie the night before. Check availability and book your tour here .

Day 2: Islamorada and Key Largo

Highlights: A snorkel tour, charter fishing, and catch-and-cook dinner.

The theme for day two is adventure in the upper keys! This is your day to go snorkeling at the famous John Pennekamp Coral Reef State Park – the first undersea park in the United States!

Unfortunately for Mary and I, it was very windy on this day of our Florida Keys road trip… so our snorkel tour got CANCELED! This was a huge bummer, but nature happens, my friends.

The Keys can be particularly windy so it’s not unheard of for water activities to get canceled. With that in mind, we still had a wonderful day and were able to go charter fishing in the afternoon.

Day 2 | Islamorada and Key Largo:

• Quick breakfast
• 9am snorkeling tour at John Pennekamp Coral Reef State Park (alternatively: swimming and paddle boarding at Postcard Inn’s beach)
• Lunch at The Fish House
• 1pm fishing charter trip
• Relax at Postcard Inn and get ready for dinner
• “Catch and cook” dinner at Chef Michael’s

You’ll spend a second night at your resort in Islamorada. We spent our second night at the wonderful Postcard Inn . I enjoyed having two nights in Islamorada, despite this being a pretty fast-paced 5 day Florida Keys itinerary.

Postcard Inn was a good home base to drive around the upper keys from. Plus, it was so great to have direct beach access, especially after our snorkel tour got canceled!

Quick breakfast. I recommend having a quick breakfast on day 2, because your itinerary today is pretty packed! Mary and I grabbed some food from the Starbucks by Postcard Inn (notably: the last Starbucks for 90 miles!).

Lunch at The Fish House Restaurant and Seafood Market (Key Largo). I stopped here for lunch to try their famous “Matecumbe” sauce which is essentially fresh fish simmered up with capers, shallots, and other delights. This dish has been featured multiple times on the Food Network – for good reason. Highly recommend!

Dinner at Chef Michael’s (Islamorada). For dinner, Mary and I dressed up and dined in style at Chef Michael’s (reservations recommended). Actually, we ate the fish that we caught earlier that day on our fishing trip – so fun!

This is also the place to try Lionfish – by eating it you are supporting their efforts to cull this invasive species and save the nearby reefs.

Snorkeling tour at John Pennekamp Coral Reef State Park. Ideally, you should spend the first half of your day enjoying an epic snorkeling tour off the coast of Islamorada.

Tours last 2.5 hours and depart 9am, 10:30am, 12pm, 1:30pm, and 3pm (for this itinerary, I recommend booking the 9am). Book your tour ahead of time here .

Fishing trip with Bamboo Charters . After lunch, head out on the water again but this time with Captain Matt Bellinger of Bamboo Charters. He’s an experienced fisherman, and will help you catch some Florida Keys fish no matter your experience level.

On our trip, we caught a lot of small snapper, which we saved for a catch-and-cook dinner at Chef Michael’s (arrange this with Captain Bellinger ahead of time). We also had an extremely thrilling hour-long struggle with a giant sting ray – don’t worry, we released it!

Fishing charters can be booked for 8am or 1pm, in groups up to six people, and you can choose a 4-, 6-, or 8-hour option. For this itinerary, I recommend the 4-hour 1pm-5pm option. Book your fishing charter here .

Relax at the beach. Your other job for today? Chill out and enjoy the beautiful Florida Keys beach – with direct access from Postcard Inn !

Of course Mary and I were disappointed when our snorkel tour was canceled, but this didn’t stop us from taking the paddleboards out at Postcard Inn.

Day 3: Islamorada to Big Pine Key to Key West

Highlights: A tropical fruit farm, the Seven Mile Bridge, and Cuban food in Key West.

Today you’ll get back into road trip mode, by driving down to Key West and passing over the famous Seven Mile Bridge. The total drive time from Islamorada to Key West is two hours, but you’ll take some fun stops along the way – including a picnic lunch at a very unique tropical fruit farm!

Day 3 | Islamorada to Big Pine Key to Key West:

• Check out of Postcard Inn
• Breakfast at Mangrove Mike’s
• Visit Florida Keys History & Discovery Center
• Drive to Big Pine Key (~1 hour)
• Visit Grimal Grove Tropical Fruit Farm
• Drive to Key West (~1 hour)
• Check in to The Gardens Hotel
• Cuban food for dinner and Sloppy Joe’s

I recommend staying at The Gardens Hotel in Key West. This was our home for two nights, and I loved it. This hotel is historic, quaint, and has a lovely breakfast and pool.

The location is ideal – you can walk anywhere you want to go in Key West but it’s a couple blocks back so never gets too loud at night. There’s also champagne on arrival and on site parking.

Book your stay at The Gardens Hotel here.

Breakfast at Mangrove Mike’s (Islamorada). Start your day off with the most Americana vibes diner you could imagine, just a five minute drive from Postcard Inn.

I particularly loved that they had gluten free pancakes! Definitely recommend eating breakfast here on at least one of your days in Islamorada.

Picnic lunch. For lunch, I recommend having a picnic, either at Bahia Honda State Park or at Grimal Gove (a tropical fruit grove that I share more about below!).

Dinner at El Meson de Pepe (Key West). You just have to try Cuban food in Key West and this is a great family-owned place to do it, recommended by locals and easy walking distance from your hotel if you stay at The Gardens Hotel.

Visit the Florida Keys History & Discovery Center (Islamorada). After breakfast, your first stop of the day should be this history museum. It’s in Islamorada and only a five-minute drive from Postcard Inn, so it’s an easy way to start our day. During our visit, I learned a LOT about the Florida Keys (did you know it was originally an overseas railroad?).

Drive the Seven Mile Bridge. Your drive today includes this incredible landmark. After passing Marathon and before reaching Big Pine Key, you must first drive over seven miles of turquoise ocean.

Take a tour of Grimal Grove . I absolutely recommend making time to stop at Grimal Grove, a tropical fruit grove in Big Pine Key with a super unique back story. This is the only breadfruit grove in the country and tours include “tropical fruit hunting” and a fun tasting session where you eat breadfruit curry, fried breadfruit, sugarcane juice, and more (AKA, lunch!).

Tours last 75-90 minutes and are available Tuesday to Saturday at 10:30am, 1pm, or 3:30pm (I recommend the 1pm time slot for this itinerary!). Book your tour here .

Get settled at your hotel. After driving another hour, you’ll arrive in Key West! Check in to your hotel (I recommend booking The Gardens Hotel ) where you’ll be staying the next two nights.

Check in involves a complimentary glass of champagne, and you may even have time to jump in the pool and say hello to the resident cat and tortoise!

Drinks and nightlife on Duval Street. After a delicious Cuban dinner, make the most of your first night in Key West with a trip to the iconic Sloppy Joe’s – the bar that Ernest Hemingway frequented in Key West. Just a warning: it’s going to be crowded… and sloppy!

The entirety of Duval Street will be bustling, so if Sloppy Joe’s isn’t your vibe then you still have plenty of bars to pick from.

Highlights: full day to explore Key West, literary walking tour, key lime pie, museums, and sunset sailboat tour.

Today you can put the car keys away and devote a full day to exploring Key West!

There are honestly so many things to do in Key West but I’m sharing my personal ideal one day schedule below. If I was to extend this 5 day Florida Keys itinerary into a full week or longer, I’d give extra days to Key West because you only really get a taster with one full day.

Still, it’s a pretty epic day. If you follow my itinerary below, you’ll spend today eating key lime pie, drinking Cuban coffee, exploring on a literary tour, visiting historic sites, and sailing into the sunset with a drink in hand!

Day 4 | Key West:

• Breakfast at The Gardens Hotel
• Coffee from Cuban Coffee Queen Roasters
• 10am Literary Walking Tour by Key West Literary Seminars
• Lunch at Date & Thyme
• Eat some key lime pie
• Museum visit
• Sunset sailing tour with drinks and live music
• Dinner at Half Shell Raw Bar

We stayed a second night at The Gardens Hotel , and I recommend you do, too. I took advantage of the hotel’s amenities by swimming in the pool early in the morning!

Key West is the highlight of the Florida Keys for many people, so you definitely want one full day and two nights here.

Breakfast at The Gardens Hotel . Since our hotel was a bed and breakfast, we just went downstairs to eat a lovely breakfast out on the garden patio!

Coffee at Cuban Coffee Queen. This was a great stop to try the classic Cuban cafe con leche.

Lunch at Date & Thyme. You can really eat lunch anywhere today, but my personal recommendation would be this lovely organic market and cafe. They specialize in grab & go meals like wraps (and ice cream sandwiches!) and have plenty of vegan and gluten free options.

ALL the key lime pie. You’re in Key West, after all, so dedicate some time today to trying key lime pie! We did this directly after lunch.

Top 3 places to get key lime pie in Key West:

• Kermit’s Key West Key Lime Pie Shoppe
• Key West Key Lime Pie Company
• Key Lime Pie Bakery

RELATED | Where to Find Gluten Free Key Lime Pie in Key West

Dinner at Half Shell Raw Bar. For dinner tonight, embrace being by the seaside and head to this casual and quirky bar located in the Key West Historic Seaport.

It will be convenient after your sunset sailing trip ends (more on that, below!). I recommend at least one platter of oysters.

Go on a literary walking tour. Key West is known for its vibrant literary history. If, like me, that interests you, then be sure to go on this 1.5 hour tour. You’ll walk through the Old Town of Key West, visiting the homes and haunts of writers like Ernest Hemingway, Robert Frost, Tennessee Williams, Shel Silverstein, and Elizabeth Bishop.

Tours are offered Sundays and Wednesdays at 10am. If that doesn’t match your schedule, you can contact them about a private tour. The cost is $30 per person, and you can book your tour here .

Visit Judy Blume’s bookstore, Books and Books. This is another one for my fellow book worms. Whether or not you go on the literary walking tour you should definitely check out the Books and Books bookstore – this is owned by none other than Key West local author, Judy Blume! You may even see her during your visit.

Explore Key West’s historic sights. After your literary morning, lunch, and a sampling of key lime pie, it’s time to spend your afternoon on more traditional touristic pursuits.

Key West has SO many museums and historic sights. You can really only scratch the surface in one day (but don’t worry, you’ll also have time to visit some sights tomorrow morning).

Here are some museums and sights to see in Key West:

• Harry S. Truman Little White House
• Key West Lighthouse and Keeper’s Quarters
• Ernest Hemingway Home and Museum
• Mel Fisher Maritime Museum
• Key West Aquarium
• Tennessee Williams Museum

Personally, Mary and I chose to visit the Mel Fisher Maritime Museum this afternoon. That may seem like an odd choice but we really wanted to see some of the less well-known side of Key West and this museum was fascinating!

Take a sunset sailing trip . Finally, end your day in Key West with an incredible sunset sailboat trip out into the ocean, complete with complimentary cocktails and live music.

Mary and I took this exact sailing trip with Sebago Watersports and it was such a lovely way to end the day. There’s nothing like a Key West sunset seen from the ocean!

Book your sailing tour here.

Day 5: Key West to Marathon

Highlights: Southernmost Point, Ernest Hemingway Museum, Key West Lighthouse, Turtle Hospital, and a stunning beach resort.

Drive time: 1 hour

This is the final full day of your 5 day Florida Keys itinerary, but it’s still packed full of fun activities!

You’ll spend the morning exploring more of Key West, including the Southernmost Point and any museums you missed the day before. Then, you’ll drive north to Marathon where you’ll tour the famous Turtle Hospital, and check in to your hotel where you’ll have an incredible al fresco dinner by the beach.

Day 5 | Key West to Marathon:

• Breakfast at The Gardens Hotel (alternatively Green Pineapple cafe)
• Check out and hold luggage
• See more Key West sights
• Lobster pizza lunch at the Seaside Cafe at the Mansion
• Drive to Marathon
• Check in to Isla Bella Beach Resort
• Turtle Hospital Tour
• Relax at Isla Bella
• Dinner at Mahina at Isla Bella

You have a couple options of where to stay tonight, depending on when your flight home is. I recommend staying the night in Marathon, before driving back to Miami Airport the following morning. This maximizes your time and gives you 5 full days in the Florida Keys.

Alternatively, if you are flying home on day 5, then you may have to skip some of the itinerary below to drive back to Miami Airport in time for your flight.

Personally, on our final night in the Florida Keys we stayed at Isla Bella Beach Resort in Marathon. This was an incredible accommodation to end our trip on.

It’s luxurious yet surprisingly affordable, directly on the water with pools, beaches, bikes, and beautiful docks with sunrise views. There are also a few restaurants on site and this is where we had dinner – one of the best meals of our trip by far.

Book your stay at Islabella here.

Breakfast at your hotel or in town (Key West). Get an early breakfast today so you can get out and explore Key West. Either eat the complimentary breakfast at The Gardens Hotel , or check out Green Pineapple Cafe , a favorite of mine which opens at 8:30am.

Lunch at Seaside Cafe at the Mansion . Before you depart Key West, grab a quick lunch at this truly iconic restaurant that’s just steps from the Southernmost Point. Come here for their famous lobster pizza – it will not disappoint!

Dinner at Mahina at Isla Bella . Dress up and enjoy a final dinner in the Florida Keys at this Polynesian inspired restaurant at Islabella, where you can dine al fresco under the stars with a backdrop of ocean waves.

The filet mignon is to die for, and top it off with a key lime pie martini! Reservations required.

Spend the morning exploring Key West. There is so much to see in Key West so you’re bound to have some places you still want to go after your full day in Key West yesterday. This is your time to visit them – just check out and have your hotel hold your luggage first!

On our final morning in Key West, Mary and I climbed up the Key West Lighthouse , before taking a tour of the Ernest Hemingway Home (a MUST when in Key West!) and hugging The Kapok Tree .

Then, we checked out the Southernmost Point marker, before getting a lobster pizza lunch. It was a pretty packed morning!

You could easily do the same, or change it up and visit any of the other sights I listed previously.

Turtle Hospital tour (Marathon). This was one of the highlights of my whole Florida Keys road trip! Marathon is home to a world class sea turtle rehabilitation center, and it’s actually open to the public to visit.

Tours are offered on the half hour, from 9am to 4pm, and cost $35 per person. Reservations are highly recommended! Book your tour here .

Relax at Isla Bella . After your turtle hospital tour, return to your hotel and relax before dinner. Soak up your final hours in the Florida Keys!

If you stay at Isla Bella Beach Resort like we did, then I recommend taking a dip in one of the pools.

Final Day: Marathon to Miami Airport

Highlights: Pigeon Key, drive to Miami Airport and fly home.

Drive time: 2.5 hours

All good things must come to an end. On your final day in the Florida Keys, your main job is to check out of your hotel and drive back to the Miami Airport (~2.5 hours driving time) to return your rental car and fly home.

Be sure to give yourself ample time to drive back to Miami before your flight, especially if you’re driving on a Friday or Sunday, due to traffic!

If you have time before you check out, consider taking the complimentary bikes at Isla Bella and riding to Pigeon Key and back. I also recommend checking out the Marketplace at Isla Bella before you leave – it’s an epic 5,000 square foot space with a cafe, perfect for picking up some souvenirs (and lunch for the road) before you depart!

If You Have More or Less Time on Your Florida Keys Roadtrip…

You can shorten or extend my suggested itinerary as needed, based on your flight times.

If I had to cut a night from my 5 day Florida Keys itinerary above, it would perhaps be the final night in Marathon (and just drive directly to Miami Airport). However, Isla Bella Beach Resort was my favorite hotel and a wonderfully relaxing way to end the trip, so it really depends on your travel style.

On the other hand, if I could add days to this itinerary and make it a full week in the Florida Keys, then I’d add a full day in Key West. Another day in Islamorada also would have been useful due to the weather cancellation of our snorkeling trip.

For the ultimate relaxation, I’d also add a couple days at Deer Run on the Atlantic , a sustainable bed and breakfast on Big Pine Key. A girl can dream!

5 Day Florida Keys Itinerary: Final Thoughts

That completes my 5 day Florida Keys road trip itinerary… I hope it’s helpful to you as you plan your own trip to the Florida Keys.

If you have any questions, just leave me a comment below. Happy traveling, and enjoy the Florida Keys!

Check out my other Florida Keys blog posts…

Best Places to Stay in the Florida Keys

Gluten Free Key West and the Florida Keys: Complete Guide

Where to Find Gluten Free Key Lime Pie in Key West

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12 places you should visit in the florida keys.

Coral Restoration Ecotourism in the Florida Keys

By Dalia Colón

A road trip through the Florida Keys is its own reward: a 113-mile journey across islands with some of the most jaw-droppingly gorgeous scenery you’ll ever lay eyes on. But amidst the topaz waters, diving pelicans and lush mangroves are a treasure trove of attractions that are educational, historical or just plain fun.

Here are a dozen of the best things to do in the Florida Keys, from top to bottom.

Two words: Underwater park. John Pennekamp Coral Reef State Park is the first undersea park in the country… and the first place you should go when you arrive in the Florida Keys. There are endless ways to explore this aquatic attraction, including kayaking through the mangroves, snorkeling or scuba diving and setting out on a glass-bottom boat tour.

The African Queen Canal Cruise is another fun way to explore Key Largo. Hop aboard the famed vessel—yes, it’s the one made famous by the 1951 movie starring Humphrey Bogart and Katharine Hepburn—and embark on a 90-minute sightseeing cruise departing from Marina del Mar. Dinner cruises are also available. 

Theater of the Sea combines the pizzazz of a marine park with the charm of a family-owned attraction.

Theater of the Sea combines the pizzazz of a marine park with the charm of a family-owned attraction. Watch a sea lion show, hold a parrot and enjoy a bottomless boat ride. The park’s animal interaction programs—including swimming with dolphins—are sure to make a splash. (See what we did there?)

Although your vacation may last only a few days or weeks, the history of the Keys dates back thousands of years. Get up to speed with a visit to the Keys History and Discovery Center , located on the grounds of the Islander Resort. In addition to rotating exhibits, the museum’s permanent collection of photos and memorabilia highlights the area’s Native American life, shipwrecks and more with photos, models and artifacts.

Love dolphins? Do a deep dive into the life of the aquatic mammals at the Dolphin Research Center on Grassy Key, near Marathon. Watch the dolphin and sea lion shows, chat with trainers and cool off at the sprayground. For next-level fun, enroll your tween or teen in Dolphin Camp, or splurge on a Fantasy Dolphin Day to live out all your swimming-with-dolphins dreams.

BIG PINE KEY

Secluded Bahia Honda State Park , located on Big Pine Key, is home to more than 150 species of rare flora and fauna. But its three unspoiled beaches aren’t only for the birds; they’re also a great place for shelling, geocaching, snorkeling and other low-key activities. The park is also sought after for camping, with accommodations ranging from primitive camp sites to glamping cabins.

There’s no shortage of animal encounters in the Keys. But for one of the most peculiar, you’ll have to visit the National Key Deer Refuge on Big Pine Key. The endangered creatures stand no more than 32 inches tall and are found only in the lower Florida Keys, so hike, bike or kayak through the preserve and keep your eyes peeled for these beautiful creatures.

Pay your respects to one of Key West’s most legendary residents with a visit to the Ernest Hemingway Home and Museum . As you stroll through the gardens and pet the six-toed cats—descendants of the writer’s own pets—imagine the Nobel Prize winner working on manuscripts when he lived in the house during the most prolific decade of his career, the 1930s. In the bookstore and gift shop, take home a souvenir to serve as your own muse.

The Key West Butterfly and Nature Conservatory is located on Duval Street, but it’s about as far away from the famous thoroughfare’s excesses as you can get. Whether you’re looking for family-friendly fun or you just need someplace to catch your breath, a few hours inside this glass-enclosed conservatory surrounded by butterflies and birds should do the trick.

When the sun goes down, the fun heats up at Mallory Square , home of Key West’s nightly sunset celebration. Jugglers, tightrope walkers, sword swallowers, buskers and other colorful characters put on a family-friendly show for your entertainment—and hopefully, for your generous tips.

Sure, it’s touristy. But no visit to Key West would be complete without a photo op at the Southernmost Point . The oversized buoy landmark represents the lowest spot on the map of the Continental United States.

DRY TORTUGAS

Just when you thought the Keys were as remote as you could get, there’s Dry Tortugas National Park . This conglomerate of islands 70 miles west of Key West is accessible only by boat or seaplane. But not to worry; even if you don’t have your own transportation, you can ride the Yankee Freedom ferry from Key West to Garden Key and still explore the park’s historic Fort Jefferson; snorkel, dive or swim in the clear waters; enjoy breathtaking birdwatching; and pitch your tent under the stars.

For more fun things to do in the Florida Keys, check out fla-keys.com .

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The Ultimate Guide To The Florida Keys

Marisa Spyker is the Senior Writer at Southern Living, where she enjoys dabbling in stories throughout the magazine, from gorgeous home features to profiles of the South's creatives. Prior to joining the team in 2019, Marisa was an editor at Coastal Living, coastalliving.com, and Luxe Interiors + Design. Her career spans nearly 15 years, much of which has been spent staring at photos of pretty homes and gleaning inspiration for her next beach vacation.

While born and raised in South Florida and a proud University of Florida alum (Go Gators!), she currently lives with her husband and two daughters in Santa Cruz, California. She can often be found schooling West Coasters on the joys of Southern charm and Key Lime Pie.

When it comes to vacation getaways, Florida spoils us with options—whether you're the type that pines for a cosmopolitan city or vast areas of white-sand beaches. But when you live in the land of vacation, where do you go for your escape? For many Sunshine Staters, the answer is the Florida Keys .

As a kid growing up in Fort Lauderdale, this laid-back paradise was my family's getaway of choice. The appeal wasn't so much about  the beaches  (though there are plenty of them). It is the feeling of escaping to an undiscovered utopia. Water surrounds you in what seems like a million shades of blue in the Florida Keys. Nearly every wrong turn leads you to a shady swimming hole with views for miles, and if you venture out into the wild blue yonder, the underwater coral kingdoms are teeming with color and sea life. But while it may feel otherworldly in its beauty and seclusion, the real magic of the islands is their accessibility. Fly into Miami in the morning, and you can be island-side chowing down on a fresh mahi mahi sandwich by lunch.

So What Are The Florida Keys?

Spilling out south from the Florida peninsula, this dreamy archipelago forms a beauty trail comprising hundreds of (mostly uninhabited) islands. The Overseas Highway connects 44 islands, a 113-mile road from Key Largo to  Key West —the most famous among the bunch. While each island is a worthy destination, the draw here is in the journey. While heading south, you'll leapfrog from island to island via a whopping 42 bridges, including the famous 7-mile bridge. Make it to the end—with character-filled Key West as its grand finale, you'll definitely want to—and you'll be closer to Cuba than the Florida mainland.

When To Visit

With year-round balmy temperatures, the Keys draw tourists near and far every season. In wintertime, crowds descend, searching for the sweet spot in favorable temps and low humidity. But you'll find the best deals in late spring or summer (if you can handle the sticky heat). The same rings true for fall, but beware of hurricane season (most active between August and October), and be prepared with a backup plan should the weather damper your getaway.

Where To Stay

The beauty of the Florida Keys is that, with an entire length that takes just over two hours to drive (if you're beelining it—which no one does), you don't have to park in just one place. Each island has its perks and personality, from laid-back Islamorada to the funky and, at times, raucous Key West. The best way to see the Keys is undoubtedly by car: Most visitors fly into Miami and experience the islands in succession, staying a couple of nights here and there, conveniently making a vacation that unfolds nicely. You can first kick back and get some sun at the  Bungalows Key Largo , an adults-only all-inclusive resort, then amp things up with some water-bound fun in Islamorada.  The Moorings  is a dreamy place to post up and round things out at a cozy B&B smack in the middle of the Key West action. With five distinct regions to explore—Key Largo, Islamorada, Marathon, Big Pine Key, and Key West—there's more than enough to round out a week (or more).

What To Do: Key Largo

Kick off your Keys journey at the chain's first and longest island, offering 33 miles of sun-drenched beauty and an underwater dreamland that attracts explorers from across the globe. As the self-proclaimed Dive Capital of the World, Key Largo is home to an impressive reef system that includes  John Pennekamp State Park  (the first underwater preserve in the U.S.) and the U.S.S. Spiegel, a 510-foot landing ship dock—intentionally sunk to create one of the world's largest artificial reefs. Pennekamp Park also offers glass-bottom boat tours and kayak rentals if you prefer to stay a little dryer while witnessing the area's aquatic wonders.

What To Do: Islamorada

Venture further south into the turquoise abyss, and you'll hit Islamorada , a village of six islands beloved for its laid-back feel and sweeping vistas (it's starred in a few Hollywood productions, including Netflix's  Bloodline ). Within the "Sportfishing Capital of the World," leaning palms frame views of calm blue-green waters dotted with activity—boats, paddlers, kayakers, and swimmers. Islamorada is the perfect place to splash around yourself. From kiteboards to wave runners, the island offers multiple places to  grab a rental . Post-splash-session, take the kids to see the sea life.  Theater of the Sea  entices with dolphin encounters, and at tourist-fave  Robbie's Marina , you can feed a school of more than 100 hungry tarpon (and their pelican friends). End your day with a rum runner at the island's world-famous  Holiday Isle Tiki Bar.

What To Do: Marathon

Right around the halfway point in the archipelago, you'll hit Marathon, a quiet little city comprising 13 separate islands. Now's your chance to cash in on that R&R— Sombrero Beach  is one of the best sandy shorelines. When you've had your fill of surf and sun, get schooled on some of the Keys' native wildlife.  The Turtle Hospital  rescues and rehabilitates endangered sea turtles, and the  Dolphin Research Center  educates on the area's beloved sea mammals (dolphins and sea lions). When you work up an appetite,  Keys Fisheries  is a must-stop whether you're parked for a few nights in Marathon or just passing through.

What To Do: Big Pine Key

If you're here for nature and could do without the crowds, Big Pine and the Lower Keys are great places to settle in. Roughly 30 miles north of Key West, the islands are rife with low-key activity both on water and land, yet a quick (and beautiful) drive to all the action.  Bahia Honda State Park  offers it all—swimming, camping, fishing, boating, excellent birding, and even a hike that drops you off at the top of the Old Bahia Honda Bridge (with a bird's eye view of the entire island). And while it may be quiet, you won't need to look far for some sundown refreshments. Drive the Overseas Highway, and you'll find plenty of casual seafood-and-beer joints ( No Name Pub  is a perennial favorite).

What To Do: Key West

You've reached the end—but things aren't slowing down. Measuring little more than seven square miles, this famous Key (once home to authors Ernest Hemingway and Tennessee Williams) has all the makings of a dynamite vacation—beaches, history, food, sunsets, and some great bars. Once you post up at  home away from home , ditch the car in favor of two wheels and go out and explore. The Hemingway House is a charming glimpse of island architecture and the author's famous six-toed cats. The brightly painted buoy that marks the Southernmost Point of the U.S. is a beloved photo opp, and the watering holes along Duval Street will keep you occupied into the wee hours of the night. (Make sure not to miss the sunset celebration at  Mallory Square .)

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The Ultimate Florida Keys Road Trip Itinerary (Best Stops!)

June 10, 2022 //  by  Florida Trippers

If you are looking for a guide to the ultimate Florida Keys road trip itinerary, we have you covered with all the best places to stop!

We have put together an epic itinerary for a road trip to Key West from Miami . Trust us when we say we have picked out the best stops along the way! We have you covered with activities, things to do, as well as hotel and tour suggestions!

Planning your trip to Key West last minute?

Make sure to book ahead! Hotels and tours often sell out the closer you get to your trip. Here are our top picks for Key West!

Top Experiences And Tours In Key West:

• Dolphin Watching And Snorkeling Eco Tour (Top pick!)
• Schooner Sunset Sail (2 hours)
• Reef Snorkel From Key West (Includes breakfast and mimosas)
• Hop-On Hop-Off Trolley Tour (Great way to see the city)

Top Places To Stay In Key West:

• Margaritaville Beach House Key West (Modern mid-range)
• Blue Marlin Motel (Affordable in downtown)
• Hampton Inn Key West (Waterfront with pool)
• Wicker Guesthouse (Great location!)

You can make the trip your own by choosing stops that best fit your personal interests. Or if you want a personalized trip experience checkout our e-book for amazing personalized touches on the best stops! Take as little or as much time as you have. You can do a quick day trip if you don’t mind a quick-paced trip, a weekend get-a-way, or spend a week leisurely visiting all the stops linked below! 

To adventuring outdoors at state parks, to going offshore to visit Dry Tortugas national park, to snorkeling the only living US coral reef, to fun stops for families and adults like where you can spot the Key Deer or feed tarpon, to visiting Key West and all the best beaches along the way, trust us this itinerary for the best road trip to the Florida Keys that is action-packed!

Before you plan your trip, make sure to check out The Best Times To Visit The Keys where we break down each month and talk all things weather!

How long does the Florida Keys road trip take?

If you were to drive non-stop from Miami to Key West on your Florida Keys road trip the 165 miles journey would take you just over 3 hours. Meaning you can decide the perfect amount of time to spend on your Florida Keys drive from Miami!

How long should you take on your Florida Keys itinerary?

You could make it a day trip, a weekend trip, or a week-long trip! The choice is yours! We have put together a list of the best places to stop on a drive from Miami to Key West. Stop at one, or stop at all, meaning you can put together your very own trip curated to your own interests and travel style.

OR take the guesswork out of your itinerary, and purchase our ebook that helps you plan your own trip, with unique itineraries and bonuses! You can purchase it here:   https://floridatrippers.com/florida-keys-itinerary-planning-ebook/

Best time of year to road trip the Florida Keys

Anytime! The average temperature year-round ranges from 73 to 83 degrees for the Florida Keys! And the sunshine state has an average of 270 sunny days a year, meaning there is no wrong time to plan a trip!

There are plenty of festivals throughout the year or head to the southernmost points of the US for the holidays! Just remember that hurricane season does run from June to November, meaning you might have to be a little flexible on your plans if a hurricane or tropical storm is headed towards the Florida Keys or Miami!

Best stops on your Florida Keys road trip itinerary:

Downtown miami.

The first of our epic places to stop on a drive from Miami to Key West is Downtown Miami . If you flew into MIA airport, this will be the perfect spot to explore, grab a bite to eat, visit a museum such as the Frost Museum of Science or Perez Art Museum or take a relaxing stroll along the water before heading south on your drive.

In this energy-filled town, you are sure to find plenty to explore, and perhaps take in an NBA or MLB game. If you are on a romantic getaway we have you covered with the best date nights in Miami as Miami is a city that comes alive after dark!

Biscayne Bay National Park

Who doesn’t love free Florida keys road trip stops? Biscayne Bay National Park is one of the best National parks in Florida , and it’s free to enter! On your second stop, we take you away from the busy city to explore nature. Visitors will be transported to the turquoise waters and colorful coral reefs found in this national park. Over 95% of this national park is covered by water!

The activities here range from guided eco-adventures, fishing, and boating to paddling, snorkeling, and scuba diving the shipwrecks just offshore to just relaxing! While exploring, you can always take a  boat cruise  through the docks and sail over Biscayne Bay.

The Everglades, are the second National Park on this itinerary for the Florida Keys! We have a list of all the best things to do in the Everglades for those wanting to spend more time here!  At over two million acres to explore, the Everglades provide countless activities and ways to explore this very unique ecosystem.

If you are up for an adventure, an airboat ride is a perfect way to see areas of the Everglades only seen by water. But there are plenty of biking and hiking trails ( or take a ranger-led tour) if you prefer to stay on land. Keep your eyes sharp the Everglades is a habitat for endangered and rare species like the manatee, American crocodile, and the Florida panther.

John Pennekamp Coral Reef State Park

John Pennekamp is one of the most magical of the Florida state parks and is located in the Key Largo at MM 102.5. This is a scuba divers’ dream destination for those driving in the Florida Keys and looking for a place to stop! It is actually the first undersea state park in the entire US!! It protects the only living reef in the United States, and as such is an underwater lovers’ paradise.

While here you can explore the over 70 nautical miles of beautiful coral reefs, hike along the pine trees, or snorkel along the mangroves and shoreline. We highly recommend this as one of the stops along with your Florida Keys Road Trip from Miami!! You can also book a glass bottom boat ride to see the tropical fish and the reef without having to get wet!

Key Largo is a great place to stop for the first day when road tripping the Florida Keys. There is so much to do here in Key Largo! Known as the “Dive Capital of the World,” you will find beautiful beaches with pristine waters. While it does in fact boast those things, there’s a whole island of adventure waiting for you at MM 102.

There are plenty of beaches to explore, an offshore shipwreck and coral reef, explore water sports like jet skiing, paddle boarding, kayaking or charter a boat for some fishing! Plus, there are tons of amazing restaurants to enjoy fresh seafood on your visit.

Windley Key Fossil Reef State Park

Windley Key Fossil Reef State Park is one of our favorite places to visit in the Florida Keys! Windley Key State Park is a historic site that doubles as a geological area that is formed by fossilized Key Largo Limestone. The entrance fee is $2.50 a person is a perfect way to spend a full day or even just a few hours it makes for an inexpensive stop on a Florida Keys road trip! It is located at MM 85.5.

It is important to note that the park is closed Tuesday and Wednesday, but open Thursday through Monday. You can take one of the five self-guided tours throughout the quarry that Henry Flagler used to build his railroad or experience it at your own pace on a self-guided tour.

This is one of the best and most iconic stops on the famous Florida Overseas Highway!

Islamorada is located about 1.5 hours ( 79 miles) south of Miami at MM 88 and makes our list of the best small beach towns in Florida. The best part is that Islamorada is almost the halfway point between Miami and Key West!

There are six islands that make up Islamorada and are connected via US1. Known as the sports fishing capital of the world, there are also tons of amazing restaurants, gorgeous national parks, and tons of activities.

Make sure to check out some of the Best Islamorada Restaurants for your trip!

You can check out our full list of things to do in Islamorada here! From visiting the Theater of the sea to swimming with dolphins to a fishing charter, history of the diving museum, state, and national parks, and more!

Peak season is in December through May and the best part is you are surrounded by Gulf on one side and the Atlantic Ocean on the other! This is truly home to some of the best snorkeling in the Florida Keys!

Visit Robbie’s Waterfront to feed the tarpon

Robbie’s is probably one of the most well-known stops on your Key West road trip. Located at MM 77 to you can spend a few hours here enjoying lunch and then feed the school of over 100 massive tarpons for $2.50 per person. Kids and adults alive love to partake in feeding the fish and watching the seagulls try and catch the fish here. Fish buckets are $4.50.

The restaurant is open from 6:30 am for a sunrise breakfast until 9 pm for after dinner cocktails. Robbies also has a party boat fishing charter that leaves twice a day and includes everything you need for a fun day on the ocean. As well as sunset catamaran charters.

Dolphin Research Center

The Dolphin Research Center is located at MM 59 ( about 2 hours south of Miami), and has been providing sanctuaries to dolphins since 1984. The center’s mission is to promote education and communication between marine mammals and humans.

Open daily from 9 a.m. to 4:30 p.m, admission is $28 for adults and $23 for children. Admission includes observing the dolphins and sea lions in training sessions and interacting with each other.

In addition to the educational experiences offered, you can book a dolphin encounter where you can get up close and personal with dolphins in the water. Or even paint with a dolphin experience or a VIP trainer for the day.

The Turtle Hospital

The Turtle Hospital is located at MM 48.5 in Marathon, Florida. Since 1986, the mission at the Turtle hospital has been to rehabilitate turtles and educate the public about turtles. Open daily from 9 am to 6 pm tours run every 30 minutes.

If you love Marathon, make sure to check out some of our other favorite things to do in the Middle Keys!

Admission is $30 for adults and $15 for children. This is one of the educational Florida Keys road trip ideas. Over the 90-minute educational experience, you will watch a presentation on sea turtles, get a behind-the-scenes look at the hospital facilities and rehabilitation area, and finally the chance to feed the turtles.

Reservations can be made online!

Don’t forget to check out some of the best restaurants in Marathon Key!

Drive or walk the 7 Mile Bridge

When driving the Florida Keys the 7 Mile Bridge is located at MM 42 in Marathon. This is the bridge that connects the middle keys with the lower keys. For those who want to continue their road trip, you will have no choice but to drive over the new 7-Mile Bridge that was finished in 1982. IT is the longest bridge in the state of Florida.

But for those who want to get out stretch their legs, and smell the salty ocean breeze why not walk the old bridge or a portion of it? This bridge is important historically as it made a land route from Miami to Key West.

Bahia Honda State Park

Bahia Honda State Park is one of our favorite places to stop on the way to Key West. Located at MM 37, about 30 miles north of Key West. We have put together an entire post on all the tips for visiting Bahia Honda . It was Henry Flagler who spent $30 million to build a railroad to Key West in the early 1900s that turned Bahia Honda State Park into a tropical paradise.

Make sure to check out some of our other favorite things to do in the Lower Keys in addition to Bahia Honda!

Bahia Honda State Park costs $8 per car to enter and is the place to stop if you love palm-lined beaches, clear water, and just activities like snorkeling, camping, and swimming at one of the three beaches from sunrise to sunset!

Although make sure to arrive early on weekends and holidays because it can reach capacity.

This is truly one of the Best Beaches In The Florida Keys and you must check it out!

National Key Deer Refuge

For those looking to get up close to the Key Deer only found in the lower keys, the National Key Deer Refuge is the place for you! What makes the key deer unique is that there are only about 800 left that can only be found on Big Pine Key . This small dog-like deer is only 2 ½ feet tall and weighs just 90 pounds.

This is a free activity to spend an hour or so, visiting the visitors center and learning all about the key deer. Established in 1957, at MM 30.5 it aims to protect species of animals such as the key deer and 20 other endangered species and plants.

Please note it is against the law to feed, touch, or hunt the key deer.

Dry Tortugas National Park

The Dry Tortugas National Park is the only stop on this Florida Keys road trip guide that is only accessible by private or  chartered boat tour ,  chartered seaplane  tour, or the  Yankee Freedom Ferry . 

If you want to add this stop to your Florida Keys road trip we highly recommend booking your dates as early as possible! The Dry Tortugas are a group of seven small islands 80 miles off the coast of Key West. Located in the Gulf of Mexico its iconic red brick Fort Jefferson transports visitors back in time. You will be in awe of how beautiful the water is, and how remote this national park truly is!

For those into camping and stargazing , this is your place! Just remember you must pack everything in and out with you! Check out  our guide  to avoid the big mistakes plus tips when visiting  Dry Tortugas National Park !

Key West is as far south as you can drive on this Florida Keys itinerary! At MM 0, you will find the southernmost point of the continental US! There are so many things to do here in Key West! Don’t let the party atmosphere scare you away from visiting. There are historical sights like Ernest Hemingway or Truman winter home, beaches, amazing restaurants , and plenty of activities to enjoy after the sun sets.

We have an entire post dedicated to the best tours in Key West from those craving adventure to laid-back food and walking tours!

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park is one of the hidden gems on this Florida keys driving itinerary. You will be mesmerized by the gorgeous blue water inviting you in for a swim or snorkel. Plus, the beach area is super instagrammable!

It is also the southernmost  state park  in the continental US and has our vote as one of the  best Florida Keys state parks! The cost to enter per car is $6.50 and is open from 8 am-5 pm daily.

Built in the 1840s, as a series of forts to protect the southern coast after the conflict of the War of 1812 and used during the Civil War and Spanish American War, it was named after US President Zachary Taylor.

Smathers Beach

The last stop on your Florida Keys driving guide is Smathers beach ! This gorgeous white sand beach is the best beach to go for those looking for real sand, as most beaches in Key West are pebble or rock. The imported white sand is the perfect place to relax and swim or snorkel in the water. All of the usual facilities are present here like parking and showers. 

The last stop on our Florida Keys road trip is the perfect place to relax and unwind before your drive back to Miami!

Where to stay on your Florida Keys road trip itinerary

Key west marriott beachside.

For those looking to stay in Key West, we highly recommend staying at Key West Marriott Beachside , like we did on our last trip to the area! But have also put together a list of the best luxury hotels in Key West.

 The resort is located on the oceanfront with a large pool as the centerpiece of the resort. At the hotel’s marina, you can rent jet skis, kayaks, and paddleboards.

Plus, there is a complimentary hotel shuttle downtown multiple times daily meaning you don’t have to bother with trying to find parking. This is truly one of the Best Places To Stay In Key West!

Many of the balconies are oceanfront allowing you to relax and enjoy a sunset or ocean breeze from your town room!

Check Rates:  Booking.com

We give Bakers Cay resort in Key Largo a 10/10! Located just over an hour from Miami, this could be the perfect spot to spend your first night on your Florida Keys road trip! This cool and unique hotel features gorgeously appointed rooms with ocean views!

There are tons of activities that the resort provides including snorkel, boat, and dive tours! The property also features two large pools and a state-of-the-art fitness center.

Make sure to check out our list of the Best Resorts In The Florida Keys ! There are some really epic resorts featured for couples, families, and more.

Check Rates: Booking.co m

Cheeca Lodge and Spa

Cheeca Lodge and Spa is located in Islamorada, one of the cutest small towns in Florida! It is located 15 minutes from the local airport or just a 1.5-hour drive south of Miami. A stay here means relaxing in a lush tropical paradise surrounded by the turquoise waters of the ocean. This is truly one of the best luxury hotels in Florida!

The property features a golf course, restaurants, pools, sea kayaks and bicycles for guests to use, Camp Cheeca for children, and an ocean-front bar! The rooms here are luxurious with all the amenities one could want and balconies to enjoy the ocean view or golf and lagoon views.

Check Rates: booking.com

Faro Blanco Resort & Yacht Club

Marathon is just over 2 hours (114 miles) from Miami making it the perfect place to stop for the night on your Florida Keys vacation itinerary. Don’t let the resort and yacht club scare you the property is reasonably priced averaging $230 a night!

The resort is on the water and features modern rooms, with a gorgeous pool and onsite restaurant. It is easy to spot by its historic lighthouse right on the bay.

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The best time to visit the Florida Keys

Dec 18, 2021 • 6 min read

With consistent temperatures and a full calendar of events, the Florida Keys is a great year-round destination © Matt Munro / Lonely Planet

Composed of hundreds of islands (or keys) that stretch nearly 200 square miles, the Florida Keys is ripe for exploration. But when should you make your tropical journey happen?

Compared to other corners of the United States , the Florida Keys has consistently warm temperatures, with highs rarely dropping below 70 degrees Fahrenheit. While the pleasantness of its climate and the vibrancy of its residents are constants, factors – spanning quirky cultural attractions to the likelihood of weather-related events – will help you nail down your plans. So, let’s find that perfect time for your next trip to the Florida Keys. 

Go November through February to feel the energy and heat

As much of the rest of the country combat cold temperatures, snow or a mix of the two, the Florida Keys remain delightfully sunny. In fact, there's a name for those that opt to hibernate for months on end or own a seasonal residence in South Florida (or other traditionally warm locations): Snowbirds.

During these snowbird-filled months, things feel noticeably busier in some of the bigger towns and popular places to visit (e.g., Key Largo , Islamorada , Tavernier, Marathon and Key West ) – there is a bit more traffic, restaurant waits are longer and the bar scene is, well, just as crazy as it is any other time of year. With a primed climate – high temperatures are typically in the mid- to upper-70s – and a unique tropics-meets-winter holiday charm, it’s no wonder so many opt to hit the Florida Keys this time of year.

Enjoy festivals and parties before the heat arrives from March through May

If you want to sneak in a Florida Keys adventure before the thermostat reads a very humid 90 degrees, this is the time to do it. March through May is optimal for a number of activities: fishing, spring festivals and a wonderful balance of locals and tourists.

Throughout the Florida Keys, you can visibly notice the snowbirds heading back north. But, between raucous St. Patrick’s Day celebrations, the Conch Republic Independence Celebration in Key West and an influx of Spring Breakers, there's plenty to keep folks heading here, too.

Get a bargain travel deal from June through October

Those dreamy waterside resorts and cottages that the Florida Keys are known for certainly aren’t cheap. For those looking for a bargain , the summer to early fall time frame is the time to make it happen. These bargains come with a few asterisks.

It is typically super-humid and hot during the summer months, so you’ll want to pack accordingly. Also, June 1 through November 30 is the Atlantic hurricane season, with September and October typically being the most active. So, you’ll want to keep an extra-close eye on the weather this time of year. But, for many, these caveats are easily worth the extra dough you’ll save.

Enjoy cultural events in January

With divine temperatures and cultural events galore, it’s no wonder so many folks opt to ring in a new year in the Florida Keys.

Key events: Art Under the Oaks (Tavernier), Coconut Crawl (Key Colony Beach), Florida Keys Celtic Festival (Marathon), Florida Keys Seafood Festival (Key West), Key West Food & Wine Festival.

Head to the art festivals in February

Love may be in the air on Valentine’s Day. But, art is in the air throughout the Florida Keys for much of the month, with two of the islands’ biggest annual attractions for art lovers.

Key events: Coral Head Music Fest (Marathon), Old Island Days Art Festival (Key West), Pigeon Key Art Festival (Marathon).

Experience the energy of Spring Break in March

South Florida is a Spring Break hotspot and the Florida Keys are certainly a part of the mix starting in March and running through mid-April. If you’re not a college student, St. Patrick’s Day is always an all-ages spectacle with festivities throughout the islands.

Key events: Islamorada Seafood Festival, Key Colony Beach St. Patrick’s Day Parade, Marathon Seafood Festival, St. Patrick’s Day Bar Stroll (Key West).

Go fishing in April

For fishers, April is one of the best months of the year for snagging a big one. Mahi mahi, tarpon, wahoo, blue marlin and yellowtail are in their prime, so plan for a fishing adventure or two.

Key events: Conch Republic Independence Celebration (Key West), 7 Mile Bridge Run (Knights Key to Pigeon Key ).

May brings the start of the heat

You can feel the spring temperatures slowly starting to shift to summer heat. With this, the snowbirds and masses of tourists that had taken advantage of cooler temps start to taper off.

Key events: Cuban American Heritage Festival (Key West), Key West Songwriters Festival, Queen Mother Festival (Key West).

June is the start of hurricane season

The heat is on and so is hurricane season. June through November, you’ll want to keep an eye on weather systems developing in the Atlantic Ocean and Gulf of Mexico that may affect your trip.

Key events: Florida Keys Guitar Festival (Marathon), Key West Pride Week, Mango Fest (Key West).

July celebrates one very famous pie

A darling of dessert menus everywhere, you can celebrate your love of key lime pie at the Key Lime Festival this month. You’ll want that slice of pie extra cool as the weather is scorching throughout July.

Key events: Hemingway Days Festival (Key West), Key Lime Festival (Key West), Spirit of Islamorada 4th of July Festival, Underwater Music Festival ( Looe Key ).

Get your lobster fix in August

The ocean water is at its hottest in the Florida Keys in August, so dive in. You can celebrate a fellow ocean swimmer – the lobster – at the Key West LobsterFest, too.

Key events: Key West LobsterFest, Kilts in the Keys (Marathon), Tropical Heat (Key West).

Enjoy less crowds in September

Family road trips come to a screeching halt and the islands have a noticeably less family-filled vibe. 

Key events: Florida Keys Birding & Wildlife Festival ( Big Pine Key ), Womenfest (Key West), Key West Brew Fest.

Get dressed up for an ultimate Halloween celebration in October

For Halloween fans, if getting creatively bedazzled for just one day isn’t enough, you can dress up and party for 10 consecutive days at Fantasy Fest in Key West. For the Halloween traditionalists, there is plenty to do throughout the islands on the big day and leading up to it.

Key events: Fantasy Fest (Key West), Goombay Festival (Key West), Reef Fest (Key Largo), Zombie Bike Ride of the Living Dead (Big Pine Key).

Enjoy the slower pace and cooler temperature of November

Wedged between Halloween and a holiday-filled December, November feels somewhat quiet. High temperatures hover around a pleasant 80 degrees Fahrenheit.

Key events: Key West Film Festival, Taste of the Islands (Marathon).

Bring in the holidays in December

The holidays are celebrated on land, by boat and via seemingly every mode in between. As colorful as The Florida Keys are year-round, things feel that much more cheery and vibrant to close out the year.

Key events: Big Pine & Lower Keys Island Art Festival, Key West Holiday Parade, Key West Lighted Boat Parade.

You might also like: The best things you can do for free in Key West 12 best things to do in Florida, from rockets and rollercoasters to the Everglades Plan your next vacation to one of these top destinations in Florida

This article was first published Sep 30, 2021 and updated Dec 18, 2021.

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8 Tips For Exploring The Florida Keys

Mia2you / Shutterstock

• Destinations
• Florida Keys
• United States

There are over 800 islands in the Florida Keys stretching over 180 miles. As you drive the Overseas Highway, you’ll come across some fascinating people, delicious and fresh food, and interesting stops.

Though Key West is the largest and most well-known city in the Keys, there are many more waiting for you. We’ve included tips for quirky, interesting, and fun stops on your next visit to the Florida Keys.

1. Travel The Overseas Highway Through The Keys

The Overseas Highway is full of history, beginning with Standard Oil tycoon Henry Flagler. Flagler’s legacy weaves throughout the Sunshine State.

Once he visited St. Augustine , Flagler fell in love with Florida. He saw the potential for new entrepreneurial endeavors, including hotels and transportation.

Henry Flagler was a visionary who saw a problem and created a solution. In this case, there was a need for transportation for wealthy Northerners who wanted to spend their winters in Florida. And there was a need for accommodations.

Flagler’s first hotel, the Ponce de Leon, opened in 1888, solving the dilemma of lodging. But transportation from up north to Florida was still difficult. However, Flagler had a solution: Create a railroad.

And thus, the East Coast Railway was born. Not only did Henry Flagler solve the northern winter migration problem, but he also offered lodging options.

In 1896 the East Coast Railway stretched from St. Augustine down to Biscayne Bay. Flagler had brought tourism to the state of Florida.

With a population of 20,000, Key West was the state’s most populated city and the United States’ closest deepwater port to the proposed Panama Canal.

Once again, Flagler caught the vision and expanded the railway from Biscayne Bay to Key West. However, it was dangerous work, and the potential of hurricanes was a concern.

Three hurricanes over five years caused heavy damage to the railway. It was the Labor Day hurricane of 1935 that sealed its fate.

With winds of 200 miles per hour and a storm surge over 17.5 feet, the hurricane heavily damaged and washed out several rail sections of the rail line. The railroad was not able to rebuild the destroyed rail line due to financial constraints.

The current Overseas Highway was built along the railbed, and as you drive along the highway, you’ll spot remains of the original railway bridges. The most photographed rail bridge is the one that connects Bahia Honda to Spanish Harbor Key.

Stretching for 113 miles, the Overseas Highway runs from Miami to Key West. Though it only takes a short four hours to traverse, take your time to stop and explore along the way.

Sheryl Chapman / Shutterstock

2. All Aboard The African Queen On Key Largo

Key Largo is the first stop along the Overseas Highway, and it’s where you’ll discover the first of many quirky finds in the Florida Keys.

The restored African Queen , used in the 1951 movie The African Queen is kept at the Marina Del Mar. The vessel was built in Lytham Shipbuilding in England in 1912 and was named the S/L Livingstone .

In 1951 John Huston saw the vessel and commissioned her for his movie The African Queen , starring Henry Bogart and Katherine Hepburn.

Don’t miss a piece of history! The African Queen is available for cruises. The 1.5-hour tour takes you through the Port Largo Canal.

3. Gather At The Caribbean Club On Key Largo

It seems you can hardly walk a mile or two without running into a slice of history head-on. The Caribbean Club in Key Largo has been a gathering spot for visitors and locals alike since 1938.

The Caribbean Club was the final project of Carl G. Fisher. Fisher was among the wealthy entrepreneurs of the early 1900s. He, along with a partner, purchased an interest in the U.S. patent to manufacture acetylene headlights, the forerunners of the electric headlights we use today.

Fisher’s firm furnished nearly every headlight used on U.S. automobiles at the time, which enabled him to amass a substantial fortune. That fortune, however, was wiped out during the stock market crash of 1929.

Following the crash, Fisher settled in Miami Beach, where he lived in a small cottage.

At the end of his career, Fisher took on one last project. This final project was building the Caribbean Club. The Caribbean Club was intended to be a poor man’s fishing retreat on Key Largo.

The Caribbean Club opened its doors in 1938 and included a small hotel, restaurant, and bar. Today only the bar remains, and it is the oldest bar in the Upper Keys. Following Fisher’s death in 1939, the resort became a gambling establishment.

In 1947 the Caribbean Club hotel and bar was used as the inspiration for the screenplay Key Largo , starring Humphrey Bogart and Lauren Bacall. The film included shots of the exterior of the club. The Caribbean Club has also been used most recently to film the Netflix series Bloodline .

In 1948, the Caribbean Club was purchased by the Krone family, and in 1963, Lefty and Ruth Whitehurst purchased the property. Today the Caribbean Club remains in the Whitehurst family and is run by the Whitehurst’s three children and two grandchildren.

Simon Dannhauer / Shutterstock

4. Explore Bahia Honda State Park On Big Pine Key

Whether you opt to spend the night on board your boat or spend the day exploring Bahia Honda State Park , a stop at this iconic park is a must-do on a road trip through the Florida Keys. The standout feature is the old rail bridge.

Take a hike and see it up close. One feature of Bahia State Park that we love is staying overnight. The park allows boaters to tie up on the dock, but due to the heavy influx of boaters in the Florida Keys, we suggest calling for reservations several months in advance. Dogs are allowed in the park, but not on the beaches, tour or rental boats, or in buildings (unless they are guide dogs). Note that they must be kept on leashes at all times.

Chuck Wagner / Shutterstock

5. Experience Another Piece Of History At No Name Pub On Big Pine Key

Let’s head back in time again. From 1931 to 1936, No Name Pub was a general store and a bait and tackle shop. In 1936, the owners built a small room onto the structure as a restaurant, and the Pub was created.

To build up the business, the owners had to get creative — after all, this was the late 1930s, and though the Great Depression had ended in 1933, people were still struggling economically. There was a storage room upstairs that was not being used for business purposes. The owners cleaned it up and opened that old upstairs storage area as a brothel, which failed several years later.

In the 1940s, the pub grew in popularity as women would shop in the general store while the men wandered the bait and tackle shop and then gathered in the pub for a sandwich and a beer.

In the 1950s, both the general store and the bait and tackle shop closed, and the pub changed its name to No Name Pub. Its reputation spread from Key West up to Miami.

The Florida Keys in the 1970s and ’80s were wild and free. There was an excess of money flowing freely, much of it illegally gained. And No Name Pub was the place to get rowdy. Jimmy Buffett was famous and could often be spotted in the Keys, and the Pub was hopping with locals and tourists alike looking to party.

During this era, the tradition of hanging dollar bills on the walls of No Name Pub was born. Those same rowdy kids who loved to party at the Pub have grown up, and No Name Pub is still their hangout, though much less rowdy!

Locals and tourists alike head to No Name Pub for great food (the pizza is incredible, and the fish dip divine!), cold beer, and conversation, and the tradition of putting dollar bills on the walls has continued. Plan a stop at No Name Pub if you want a taste of the local flavor of the Florida Keys.

6. Plan A Stay At The Perry On Key West

The Perry Key West is what Key West was 30 years ago. Located on Stock Island, the resort is chic, paying homage to Stock Island’s fishing and maritime history.

Whether you come by plane, boat, or car, the Perry is a top choice for travelers. The hotel boasts stunning waterfront views in each of its luxurious rooms, two waterfront pools, outdoor firepits, and three on-site restaurants and bars.

The Perry is dog-friendly, so rest assured that your four-legged pals will be treated like the Very Important Dogs (VIDs) they are. There are two dog parks on-site as well, making your VID’s visit top-notch.

For boaters, the Stock Island Village Marina is ideal, with direct access to the ocean. The piers are floating, which is a boater’s dream. The marina is located on-site at the Perry Key West, and boaters can access all amenities at the Perry.

Want to get into Key West from the Perry? No problem. There is a free shuttle that will take you into Key West, a short 15-minute ride.

7. Soar Like A Bird Over To Dry Tortugas National Park

I am addicted to seaplanes, and knowing the wonky sea conditions that can crop up out in the Dry Tortugas, I knew I had to try the seaplane trip over to Fort Jefferson. Seaplane Adventures out of Key West is the only seaplane service permitted to serve Dry Tortugas National Park.

The flight over is about 40 minutes and allows you a birds-eye view of Key West and the Atlantic Ocean. From the plane, you’ll see sharks, sea turtles, and the giant underwater sand dunes created by the wave action.

The wreck of the Northwind , a 60-foot salvage tugboat that was attempting to recover treasure from the sunken Nuestra Senora de Atocha , a 17th Century Spanish Galleon, can sometimes be spotted as you are flying over to the national park.

Dry Tortugas is approximately 70 miles from Key West, and the 100-square-mile park is predominantly water with seven small islands. The park is only accessible by seaplane or boat.

Garden Key boasts one of the 19th century’s largest United States forts, Fort Jefferson. The fort was built to protect a strategic deepwater anchorage.

When you are out in Dry Tortugas, walk around the fort, and you can almost hear it whispering its long-held secrets.

For snorkeling enthusiasts, a visit to the Dry Tortugas is a must! We’ve spotted goliath grouper, tarpon, a shark or two, and sea turtles on our snorkels around the fort.

8. Check Out Mel Fisher’s Treasure Museum On Key West

Mel Fisher was in California and running a dive shop with his wife when the lure of treasure sang its siren song and wooed him to Florida. In 1963 Fisher uprooted his family to come to Florida’s Treasure Coast to hunt for treasure with the Real Eight group.

After 363 days of searching for the remains of the wrecked 1715 Spanish treasure fleet with no luck, on day 364, Fisher and his team hit the mother lode.

For the next 10 summers, Mel Fisher and his team continued searching and recovering treasure from the wrecked Spanish treasure fleet.

During the winter, Florida’s Treasure Coast waters are too turbulent to search for underwater treasure, so Fisher moved his winter operations to Key West.

In 1973 Fisher found the Spanish galleon Nuestra Senora de Atocha . The “Atocha mother lode,” as the find was named, has an estimated value of $450 million.

It includes 40 tons of gold and silver, emeralds from Columbia, 1,000 silver ingots, and other gold and silver artifacts. The Nuestra Señora de Atocha is known as the world’s most valuable shipwreck.

Today, Mel Fisher has many treasures from the sea available in his Key West location. To learn more about Mel Fisher and his treasure salvage operations and how you can participate in a treasure dive, visit the Mel Fisher Maritime Museum .

No matter what you choose to do on your visit to the Florida Keys, you will feel relaxed, suntanned, and full of good memories and stories to share upon your return home.

You’ll find unusual things, interesting people, and exciting fun in the Florida Keys. Relax, unwind, have a rum punch or two; you’re on island time in the Florida Keys. For more Keys inspiration, consider:

• Epic Florida Road Trip: Miami To Key West
• How To Spend An Amazing Day In Islamorada, Florida
• Key West Vs. Key Largo: 9 Key Differences Between Them

Betsi and Jim, her travel companion, travel the world while documenting their adventures and gathering travel tips to share with their readers. Betsi focuses on destinations that cater to multi-generational travelers, as well as luxury travel getaways and all-inclusive resorts.

15 Informative Tips for Planning a Florida Keys Trip You NEED to Know

A Florida Keys trip is the ultimate holiday for outdoor lovers, adventure seekers and road trip enthusiasts. Having just returned from our own road trip from Key Largo to Key West, we have compiled the best tips to help you plan and organize your trip from what to see and how to budget for all the things you may want to do. A Florida Keys road trip sets the background for an amazing vacation, well worth adding to your travel bucket list.  Read on as we share our lessons learned to help you make the most of your visit. 

What (& Where) are the Florida Keys?

What exactly are the Florida Keys? The “Florida Keys” refers to an archipelago with around 1700 islands at the southern tip of Florida, only 90 miles from Cuba. Officially, the Keys begin around 12 miles south of Miami, extending south and south-westward more than 137 square miles long. Many of these keys are actually just mangrove forests on fossilized coral beds, while others have been developed into commercial centers and holiday destinations.

A few of the main islands that you will have probably heard before include Key West, Marathon, and Key Largo.

How to Visit the Florida Keys

You may be wondering how exactly you can visit the Florida Keys if they are a collection of islands. The coolest thing about this area is that it is possible to drive from the top of the Keys all the way to the bottom via the Florida Keys Overseas HIghway which covers around 113 miles from mainland Florida to Key West. Thus, one of the best way to visit is to plan a Miami to Key West road trip that takes in all the best spots on your Florida Keys trip. 

Driving the Overseas Highway from Miami to Key West will give you the opportunity to see some of the most beautiful scenery in the state. Along your journey you will cross 42 bridges connecting some of the most interesting islands in the United States, encompassing mangrove forests and even areas with pine trees. 

Getting to the Florida Keys

The best way to get to the Florida Keys is typically to fly either to Key West International Airport or to Miami International Airport. For most visitors, the best flight options will arrive to MIA which is the perfect base to begin your trip. If you are planning a Florida Keys road trip, you will also need to rent a car. I would recommend getting a smaller car as there are small parking lot areas, your boutique hotel might have limited parking areas and parking is tough in places like Key West. 

How Many Days in the Keys?

Planning your Florida Keys trip is never easy when it comes to deciding how many days you should stay in the Keys. If you want to move quickly, you could do it in as little as 3 days, but you would be missing out on a ton. Ideally, I would suggest at least 7 days but you could easily fill your days up to 10-12 days. 

When to Plan a Florida Keys Trip?

High season for Florida is typically in the winter months as it has the best temperatures and weather, however many families (like ours) visit in the summer which also is technically hurricane season. For the most part though, hurricanes typically really begin in mid August to the end of October. We visited in mid June and the weather was hot and humid with scattered storms most days. One of the best things about visiting the Keys even during hurricane season is you know you will have a few days warning, so you can usually adjust accordingly. That said, make sure to have travel insurance if you are traveling at this time to be prepared for cancellations.

Disclosure: Some of the links in this post are affiliate links, meaning at no additional cost to you, I will earn a commission if you click through and make a purchase.

Top 15 Tips for Planning a Florida Keys Trip

If you are planning a Florida Keys trip there are a few things that you should know before you go to help your trip go more smoothly. Below are our top tips that you should keep in mind during the planning phases of your trip. Rest assured by being prepared you will have a good time and know all the best ways to experience the Keys. 

Plan to Stay in Multiple Destinations

Even though the entire drive of the Florida Keys from Miami is only about 165 miles, it is highly recommended to stay in a few different places along the Keys to fully experience it all and to avoid driving back and forth every day on the 1 lane road. We recommend staying in Key Largo and Key West for sure. If you have more time on your trip, you could also stay between the two in Islamorada. The main islands that visitors tend to stay at include Key Largo, Islamorada, Marathon and Key West. Additionally, if you plan to spend any time at the national parks, you could also spend a night in Homestead outside of Miami. During our visit we stayed in Homestead, Key Largo and Key West which was perfect for the amount of time we had. If we had a few more days, I would have loved a stay in or around Marathon.

The Keys are Expensive

The Florida Keys are not a cheap holiday destination no matter how you cut it, but it is SO worth the expense in the end. From the endless amount of water activities and tours, to accomodation and eating out all of your meals it can really add up. There are ways you can save money if you plan far in advance and really budget and plan out the things that are most important for your visit.

Camping is an option all along the keys in the various state parks. These book out WELL in advance though so you must be prepared, but that is one of the best ways to really cut your costs on a trip to this area. Also cooking some meals at your hotel can help reduce costs, or looking for hotels that provide free breakfast. We had a full kitchen at our cottage in Key Largo which was amazing.

Tipping is Expected

One of the most important things to know when planning your Florida Keys trip is that tipping is the expected norm here in everything you do. When you start adding it up each day it becomes a lot, so it is important to really budget in this extra cost for all of your guided tours, water sport adventures and of course hotels and restaurants. Even buying a cup of coffee these days comes with an extra 18% or ore tip! This is a good thing to plan into your budget in advance. If you are taking a boat tour, the sea plane over to Dry Tortugas, a snorkel adventure, a taxi, etc you will be expected to provide a tip.

It is Hot & Humid

Bring reusable water bottles.

There isn’t a huge push in Florida to reduce plastic usage as they still provide plastic bags at shops and plastic water bottles are all over, but to help reduce plastics finding their way into the ocean, we highly recommend bringing your own reusable water bottles . And since it is so hot for much of the year, I would highly recommend you take something like a hydro flask that will keep your water cold all day! We would fill up our bottles with ice in the morning, add a little water and then could refill it as the day went on. And it makes the perfect souvenir collector to add your stickers to.

Beaches are Few & Far Between

Budget for adrenaline activities.

Somehow we managed to snorkel every day of our visit to the Keys which was amazing, but it also wasn’t always cheap. Plan out the main water activities you would like to do during your visit and see if you can hit them all in one go. We really loved our day out with Fury Key West on their Ultimate Adventure H2.0. It included a quick banana boat ride, jet skiing, parasailing (see the video below for our experience!), a water playground and snorkeling in an all day boat trip. For $169, which also included breakfast and lunch this was a steal! It allowed us to try a lot of activities all in one day.  There are also great options for snorkeling right off the beach or piers in many places.

Try to Get in the Water Daily

On this note, make sure to spend some time under the water to see so much more of what is happening in the Keys! the diving and snorkeling here are really great as this is the world’s 3rd largest reef! The tropical fish and marine life are so beautiful and so abundant. We snorkeled every day and every dip under the water was a new adventure with something new and cool to see. It wasn’t always crystal clear water, but the visibility was pretty good most of the time. The Keys have everything from snorkeling off an electric boat to SNUBA for first timers. 

Bring ONLY Reef Safe Sunscreen

One of the most important factors to know when planning a trip to the Florida Keys is to bring only reef safe sunscreen with you if you plan to be in the water at all. As organizations are working hard to reduce the pollution in the waters, one of the easiest ways to help keep the coral reef alive and help restoration efforts is to make sure you are only using reef safe sunscreen. We love this brand , but you can also use this brand , which is easily available at most stores. To help reduce the amount of sunscreen we need to put on, we also always recommend wearing long sleeve swim shirts while on the water or in the water. 

Don’t Skimp on the Bug Repellent

The mosquitos are horrendous in some places and at certain times of year. During our June visit we were eaten alive at Biscayne National Park and the Everglades. For much of our visit in the Lower Keys and Middle Keys the mosquitos were minimal and were kept at bay with a quick spray. That said, if you are anything like us, make sure to come prepared. I typically spray our clothes with permethrin before going to a buggy place and get these bracelets for my son as he is a bug magnet. This time I forgot, so we had to purchase bug spray locally. Make sure to get sweat resistant as well as you will be sweaty most likely!

Pack Your Snorkel Gear

If you want to have the most flexibility in when and where you snorkel, consider bringing your own gear. It was great to have our own snorkel mask so that when an opportunity arose to snorkel we were prepared. While most tours do provide the gear, it is nice to know yours works well. In this realm, we also highly recommend bringing your own towels as none of the tours have them and you will need them all the time. We have several that we always bring on trips. Mine is this one which is large, doesn’t collect sand and dries overnight easily. My son has a quick dry towel, but also uses his Nomadix poncho as a towel and cover up. Lastly, we would recommend having a mesh lightweight tote to keep all your gear in to easily take from one place to another. 

Eat All the Key Lime

Yes, Key Lime Pie is really a big deal here and you will have the opportunity to try it at almost every restaurant. But what you really need to do is read up on it before you arrive so you can have a basic idea of what you are looking for in your pie slices. Some of the best places for key lime pie are in your regular restaurants, so you don’t have to always go out of your way to find some delicious treats. 

Eating Out is Expensive

Meals are expensive in the Florida Keys. Coming from Los Angeles, I wasn’t expecting to see prices as high as at home or even higher for what often felt like a mom and pop restaurant. While the food was always pretty amazing, it definitely wasn’t expected. If we got an appetizer and two main dishes with only water our meals were coming out to minimum $60. As such we tried to find more local places, chose appetizer sized plates more often and didn’t always eat fresh fish even though that is the best thing to eat here. That said, you will eat at some of the best restaurants without having to dress up or make reservations, so do make sure to pop into a few places! Our absolute favorite was The Fish House in Key Largo. 

Utilize the Florida Keys Website for Planning One of the best resources to plan your trip (besides us!) is the Florida Keys Visitor Website . Here you will find more information on where to eat, stay and things to do.

Take Time to Learn While Here

While a Florida Keys trip might be all about fun and adventure, there are actually some really great learning opportunities here as well. We highly recommend taking time to learn about the Coral Restoration work that is happening (and that you can volunteer to be part of if you are a diver!). Additionally, the Turtle Hospital is an amazing resource to find out all about the sea turtles that call the Keys home and how this one facility does so much to help them. If you visit, make sure to pick up one of their laminated cards to take out with you in case you see an injured turtle on your water adventures. 

Furthermore, if you are a book lover or history lover make sure to visit Ernest Hemingway’s House and if you have time the Key West Shipwreck Museum is also super cool and a must visit. Another great place to visit is Pigeon Key Island where you can learn about the old seven mile bridge and the workers who lived on this small island. While here you can also hop off the pier for some snorkeling! The Pigeon Key Tram is super cute and a great way to get out here if you don’t want to walk or if you don’t have your own bike to ride out. 

Take Guided Tours

Even though I have mentioned several times how expensive things can be on a Florida keys trip,  I will say that everytime we took a guided tour we were very happy with the money we spent. We learned so much more, saw so much more in the water and really enjoyed the day more by having someone to ask questions to. We loved so many tours we did, but the most educational tour we took was at Biscayne National Park. We did a snorkel and eco paddle tour where we learned about the history of the park, the ecology of the mangroves and saw some cool stuff under the water. 

Plan to Visit a National Park on your Florida Keys Trip

Biscayne National Park is another national park just at the top of the Keys about 20 minutes from Key Largo outside of Homestead. This national park is about 95% underwater. Here you have the option for snorkeling day trips, kayaking through mangrove forests and even sailing out to further islands. 

Lastly, not totally in the Keys, but close enough is Everglades National Park. For a quick visit, head to Royal Palms Visitor Center to see alligators and get a feel of what this park is all about. 

A Florida Keys trip is truly one of the best holiday destinations in the United States. It provides the feel of being out of the country with the Cuban culture, the chill vibes while also providing the ease of in country travel. I highly recommend putting the Florida Keys on your travel wishlist. There is so much to discover there, we are already planning our next visit.