annapolis harbour cruise

Watermark Online Reservations

Concierge or booking agent, for gift certificates click here, reservation / cancellation policy.

Events occur rain or shine. In the unlikely event that Watermark should have to cancel, we will attempt to contact you and ticket will be refunded or event rescheduled. Watermark may cancel any event because of severe weather, mechanical breakdown, or lack of participation. Tickets are non-refundable. Payment will be processed at the time of purchase. Vessel Substitution: Boat assignments are subject to change at any time. Route Change: Cruise and tour routes are subject to change at any time.

Policy Notices

Many cruises are walk-up only, with plenty of capacity. For our full cruise schedule, go to http://cruisesonthebay.com/ . Vessel assignments and cruise routes are subject to change. Please dress appropriately for the weather including sunscreen. We suggest comfortable shoes for walking tours. On our vessels, snacks and alcoholic and non-alcoholic beverages are available for purchase. Outside beverages and coolers are not allowed. Bagged lunches welcome.

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2024 Sailing Season is coming! See you April 13, 2024!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!

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Watermark Harbour Cruise

Explore this amazing attraction and discover what makes it a must-visit. Stay tuned for more details!

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Would you like to experience the enchanting waterfront charm of Annapolis, renowned as  one of the prettiest cities in the United States? If your answer is yes, then the Watermark Harbour Cruise is the perfect choice for you. Annapolis is celebrated for its stunning maritime allure, adding to its natural beauty. With the Watermark Harbour Cruise, you can take in stunning waterfront views, explore iconic landmarks, and learn about the city’s rich history and culture.

Embark on the Watermark Harbor Cruise on our Best of Annapolis Tour with Boat Cruise!

What to Know

The Watermark Harbor Cruises in Annapolis, Maryland, are highly recommended for an exciting sightseeing adventure. You will have a great time exploring the historic waterfront and nearby areas in a relaxed way, thanks to the skilled crew onboard. These cruises, operated by Watermark Cruises and Tours, include narrated tours that highlight the history of Annapolis, the United States Naval Academy, Spa Creek, the Severn River, and iconic landmarks such as the Thomas Point Lighthouse and the Chesapeake Bay Bridge.

Passengers have the flexibility to choose from a range of duration and cruise options with Watermark Cruises and Tours. One of the popular choices is the Thomas Point Lighthouse Cruise, a 40-minute tour highlighting the scenic Thomas Point Lighthouse and offering breathtaking views of the Chesapeake Bay. For those looking for a more extensive experience, Watermark also offers special cruises like the Bay to St. Michaels cruise, a day-long journey to the enchanting town of St. Michaels on Maryland's Eastern Shore.

How to Get There

Annapolis is a city with well-maintained roads and multiple means of transportation. You can drive your car to the destination, exploring the surrounding areas. Alternatively, you can opt for ride-sharing services to reach the attraction. However, the best way to visit and enjoy the Watermark Harbour Cruise is by joining guided tours. You can  book your tour with Tripshepherd , which offers an intimate and guided small-group tour experience to ensure that you have the best experience of the Watermark Harbour Cruise.

Best Time to Visit

The best time to visit the Watermark Harbour Cruise depends on you. You can have this unforgettable cruising experience while enjoying stunning waterfront views with snacks and drinks at any time you prefer. There are various options available with different cruise durations. You can choose when to visit based on your time frame and preferences. One thing is clear: you will have the best time of your life.

Highlights & Features

- Take in the views from the Annapolis harbor. You will be captivated by the picturesque Chesapeake Bay. It is a stunning cruising destination.

- Immerse yourself in iconic landmarks like the U.S. Naval Academy (USNA), the historic Annapolis Bay Bridge, and the Thomas Point Lighthouse.

- Choose from a variety of cruise lengths, from 40-minute excursions to full-day trips, to suit different schedules and preferences.

- Relax in well-maintained ships with indoor/outdoor seating and everything you need for a comfortable and enjoyable journey.

- Enjoy snacks and drinks that are available on the ship. Savoring refreshments with a stunning view is an unforgettable experience.

- Do not miss the opportunity to take pictures of the beautiful waterfront, historical architecture, and natural scenery.

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THE 10 BEST Annapolis Boat Tours

Boat tours in annapolis.

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1. Watermark Cruises and Tours

2. Schooner Woodwind Annapolis Sailing Cruises

3. Classic Sail Charters

4. Annapolis Electric Boat Rentals

5. Waypoints Annapolis

6. Family Fishing Adventures

7. Non Sea-Quitter

8. Picture Perfect Sailing

9. WindSong Charters

10. Foxglove Charters

11. Chronic Sailing

12. Chesapeake Sailing School

13. Liberte, The Schooner

14. Capitana SOS, LLC

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16. Down Time Sportfishing Charters

17. Island Chill Yacht Charters

18. Wilma Lee Skipjack Cruises

19. Dream Yacht Charters USA

20. SV Pintita

21. J World Annapolis

22. waypoints yacht charters, 23. seas the bay sailing charters, what travelers are saying.

Wine and Dinner Cruises on the Chesapeake

July can be steamy or dreamy – hot on land but much cooler on the water.  Watermark Cruises and the Schooner Woodwind offers a range of options for getting out on the scenic Severn River or the majestic Chesapeake Bay. These well- established local companies provide unique adventures of varying durations – from on-demand water taxis to foodie-favorite wine and dinner cruises.

Watermark has a fleet of boats, ranging from the popular Harbor Queen , a replica of an old river boat that leaves City Dock every few hours for a 40-minute cruise around the Annapolis Harbor to round trip cruise on a catamaran motor boat named Lady Sarah that takes passengers on a glorious round trip from the City Dock to the picturesque town of St. Michael’s on Maryland’s Eastern Shore. This perfect “day on the bay” is a double-edged treat, with fare that includes a complimentary ticket to the Maryland Maritime Museum, the boat’s docking destination in St. Michael’s. Ticket holders for the cruise have a three-hour layover in St. Michael’s, a town with many good restaurants – among them the Crab Claw (super casual) and the elegant Inn at Perry Cabin.

Other members of the Watermark fleet are the Miss Anne , a cozy 22-seater that plies the coves of Carrol’s Creek and Cabaret II, a motorized craft whose route focuses on lighthouses on the bay. And there’s one more boat in the fleet – a water taxi . Call the Watermark Captain at 410-263-2033 if you need a water taxi to take you to and from the concentration of good restaurants on the Eastport side of the Annapolis Harbor.  This low-cost on-demand service originates at the City Dock, ferrying passengers to the docks of the Annapolis Chart House , Carrol’s Creek Café and O’Leary’s Seafood Restaurant and to walking-distance destinations like Ruth’s Chris, Boatyard Bar & Grill and Lewnes Steak House.  P.S. Watermark folks are pet friendly, welcoming leashed and well-behaved dogs on most cruises.

Call Katy 410-268-7601 for more information and go to www.cruisesonthebay.com for reservations and schedule.

Schooner Woodwind & Woodwind II, a pair of gorgeous 74-foot wooden boats, offer a winning variety of on-the-water excursions ranging from daily two-hour cruises to Saturday night “Boat and Breakfast” accommodations that include a two-hour sunset sail and sunrise breakfast on the deck.  “Party Like a Sailor” events provide a taste of sailboat racing, with both schooners competing with each other during the popular Wednesday Night Races sponsored by the Annapolis Yacht Club. Reservation holders are entitled to a Cuzon Rum Punch beverage on board and another at the informal “after party” at the Boatyard Bar and Grill in Eastport.

Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings.  Tickets are still available for August 27, a Spanish-themed two-hour sail featuring four wine samples “perfectly paired with magnificent morsels” provided by prime time Annapolis caterer Palate Pleasers.  Kaye will showcase the wines of Maryland’s Dodson Vineyards at a special dinner on August 20, when the menu will include a rose paired with a ceviche of scallops and shrimp, chardonnay with jumbo lump crab salad, red with beef medallions and a floral white with a dessert torte.  At this point, there are nine remaining reservations.

Captain Kaye will celebrate Schooner Woodwinds’ 25 th anniversary in 2018 – during which time Schooner II achieved international celebrity as the “star” of the movie “Wedding Crashers.” These two photogenic schooners are the setting for corporate team building sessions, wedding rehearsals and receptions and high-end social gatherings.  Scheduled cruises happen rain or shine or with only one person on board. Their home port is the dock at the Annapolis Waterfront Hotel , where they depart for two-hour cruises at 11 am and 1:30, 4 and 6:30 pm.  Join the crew with a call to 410-263-7837 for more information and go to www.schoonerwoodwind.com for reservations and schedule.

Photos courtesy of Cruises on the Bay by Watermark and Annapolis Sailing Cruises: Schooner Woodwind .

Mary Lou Baker

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The Sailing Capital of the U.S. Is a Perfect East Coast Getaway — With Historic Charm, Tasty Seafood, and Scenic Harbor Views

Here’s what you need to know about visiting Annapolis, one of the East Coast’s best waterfront destinations.

Best Things to Do in Annapolis

Annapolis hotels.

• Where to Eat and Drink in Annapolis

Best Time to Visit Annapolis

Getting there.

The famous “crab cakes and football” line from “Wedding Crashers” may have firmly planted itself in the cultural zeitgeist 18 years ago, but there’s a lot more to Maryland than seafood and sports (although those are pretty important, too). Given its East Coast location and proximity to the Chesapeake Bay, many of Maryland’s towns and cities have waterfront access — hence, the association with the fishing and crabbing industries as well as sailing and other maritime activities.

As one of the original 13 colonies, Maryland was also influential in the shaping of the United States; in 1791, the state transferred ownership of a portion of its land to the federal government to form the country’s new capital, Washington, D.C.

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There’s perhaps no city that combines everything Maryland is known for — food, culture, and historical significance — quite like Annapolis. Home to the U.S. Naval Academy, a walkable downtown, and a robust sailing community, the state’s capital is perfect for a long weekend away or an extended visit to the Chesapeake region. 

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With a nickname like the "Sailing Capital of the U.S.,” it should come as no surprise that Annapolis plays host to various water-adjacent activities. The warmer months are particularly buzzy around Annapolis Harbor and City Dock, the heart of the historic district. 

If you’re visiting for the first time, a guided tour of the city is your best bet to cover as much ground as possible. In true Annapolis fashion, there are plenty of options to see the area by boat. Visitors who come aboard the Harbor Queen will explore Annapolis Harbor and cruise by the banks of the Naval Academy while learning about the city’s history and geography (tours are available from April through October). The Annapolis Maritime Museum & Park also offers Skipjack history tours that provide additional information about the Chesapeake Bay and its ecology. Travelers who don’t quite have their sea legs can opt for a 60-minute trolley tour around the charming streets, marinas, and high points of the city. Access to the U.S. Naval Academy is limited, but it’s certainly a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center .

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If you prefer to discover a new place on your own, be sure to walk down brick-paved Main Street and pop into its shops, art galleries, restaurants, and bars. One block away, you'll find State Circle and the Maryland State House , the only state house to have served as the nation's capital and the oldest state capital in continuous legislative use. Further out in the Annapolis Design District — about two miles from State Circle — numerous murals decorate the city. From the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) to the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local who spent 40-plus years cleaning up the trash from Annapolis streets, these murals can be appreciated via a self-guided walking tour . 

Like the city itself, the best hotels in Annapolis have touches of nautical whimsy and nod to the city’s history. Graduate Annapolis opened in the arts district in 2019 with decor “inspired by Chesapeake blue crabs, Academy colors, and old-school madras plaid.” Like other Graduate hotels, the property proudly celebrates the culture of local colleges — the U.S. Naval Academy and St. John's College. As its name suggests, Annapolis Waterfront Hotel, Autograph Collection , is conveniently located by the harbor, and it’s just a short walk to the Naval Academy. Historic Inns of Annapolis is made up of three landmark buildings in the downtown area: Maryland Inn, Robert Johnson House, and Governor Calvert House. Each house pairs 18th-century details and quaint ambiance with modern amenities (including free Wi-Fi). 

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Where to Eat and Drink in Annapolis

The culinary scene in Annapolis goes above and beyond seafood — but if you’re visiting Maryland in the summer months, oysters and blue crab should make it into your diet at some point during your trip. For a taste of a traditional Maryland crab house, there’s Cantler’s , Mike’s Crab House , or The Choptank . Chick & Ruth’s has been a city staple since the 1960s, and Iron Rooster has a popular all-day breakfast menu. For a post-dinner sweet treat, head to Annapolis Ice Cream Company , where you can indulge in homemade flavors like Funfetti cheesecake, blueberry strudel, and birthday cake. 

If you want a heaping dose of Annapolis history, add Reynolds Tavern and 1747 Pub to your itinerary. You’ll take a step back in time when you enter the tavern for traditional English afternoon tea or the cellar pub (watch out for the low ceilings) for a refreshing Pub Punch or lager. The beer garden behind the tavern also welcomes guests during the spring, summer, and early fall. For something a bit more modern, there’s Preserve for cocktails, Fox’s Den for craft beer and pizza, or Galway Bay Irish Restaurant and Pub , a lively pub on Maryland Avenue. 

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Like most other parts of Maryland, Annapolis is a true four-season destination. The warmer months, however, are ideal for adventuring out on the water. Spring is typically the best time of the year to go to Annapolis, as summer tends to become busier when sailing season kicks into high gear. 

Annapolis can easily be explored on foot, but you’ll need a car if you want to venture further into the Chesapeake region. Washington, D.C. and Baltimore are both about an hour’s drive away, depending on traffic, so flying into any of the area’s three international airports — Baltimore-Washington International Thurgood Marshall Airport (BWI), Washington Dulles International Airport (IAD), and Ronald Reagan Washington National Airport (DCA) — puts you within driving distance of Maryland’s capital.

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Harbor Queen

Harbor queen is the premier party boat offered by yacht charters on the bay by watermark..

With ample space for your guests to dine and dance under the magnificent backdrop of a starry night sky, Harbor Queen features open floor plans on both her first and second decks. With a length spanning 65’, Harbor Queen is a true Annapolis icon!

Harbor Queen is a popular waterfront venue choice for fundraisers, reunion groups, and themed parties of all sizes. She has a covered lower deck with a bar, an open forward deck, and an open top deck. She’s available for charter outside of her public tour schedule. Are you interested in learning more about the Harbor Queen’s tour schedule?

View Harbor Queen’s Floor Plan

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