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Beyond Cannolis: Exploring Boston’s North End with Context Travel

If you’re planning to visit Boston , I recommend taking the North End Boston History Tour by Context Travel to explore my favorite neighborhood in the city.

After living in Boston for nearly nine years, I thought I knew the city pretty well. I also thought I knew a fair amount about the North End, Boston’s “Little Italy,” since I once organized my own walking tour of the neighborhood when the Women in Travel Summit was in Boston, and I’ve taken numerous out-of-town visitors there to decide for themselves which bakery makes the best cannoli in town – Mike’s Pastry or Modern Pastry.

Then one damp and gray Saturday morning, I took Context Travel’s  North End Boston History Tour , “Portrait of a City.” The  docent, Leo, a history buff who works for Cambridge Public Schools, made my jaw drop on more than one occasion during my nearly four-hour experience. His tales of money, murder and mayhem went far beyond the standard walking tour script of facts and anecdotes, and had me captivated from beginning to end. 

Here are all the stops we made that morning and just a fraction of what I learned from Leo along the way:

1. Long Wharf

After meeting on the Greenway, Leo and I walked to the end of  Long Wharf, where I tried to concentrate on what he was saying despite the bitter wind whipping off Boston Harbor. There he set the stage for the rest of the tour, detailing Boston’s evolution from being a prime spot during pre-colonial days for the Messatsoosec tribe to come to fish in the summer to becoming the “greatest harbor in the Americas” during the 1700s.  

Long Wharf extended nearly a half-mile into Boston Harbor and back to State Street until the Harbor was filled in to extend the shoreline. Today this dock is used by various sightseeing cruises and tour boats.

2. State Street

To escape the wind, we walked away from the water up State Street, which once was the center of Boston’s financial power for the city’s elite, the Brahmins. We stopped across the street from the Custom House (now home to Marriott Vacation Club Pulse), where I learned the Puritans – Boston’s early settlers – referred to Boston as “the city on the hill” (influenced by future governor John Winthrop’s declaration, “We shall be as a city upon a hill, the eyes of all people are upon us”).

Leo had a binder packed with maps and other reference materials that he referenced throughout our walk.

3. Faneuil Hall

Leo told some of the juiciest stories when we stopped in front of Faneuil Hall Marketplace. Today Faneuil Hall is one of Boston’s most popular tourist attractions, but early farmers were not a fan of it. They set it on fire multiple times, worried that having to compete to sell their goods would drive down their prices.

Leo described early settlers of Boston as starving, anxious and always “ready to fight.” There were riots against impressment – Boston’s men were vulnerable to being kidnapped and forced to work on British warships – in 1747 as well as against the Stamp Act of 1765.

Colonialists also fought for entertainment. I was surprised to learn that Guy Fawkes Day, which commemorates the failed plot by Catholic activists to blow up British Parliament (and Protestant King James I) in 1605, was once one of Boston’s most popular holidays. Gangs from the North and South Ends would each parade their effigies through the streets and then meet at Faneuil Hall for an all-out brawl. The winner then burned everything in a celebratory bonfire.

Built in 1747, Faneuil Hall is now home to dozens of shops, pushcarts, restaurants, and bars, and offers entertainment in the way of street performers, musicians, outdoor movies, and more.

4. Mayor Curley’s statues

Across the street from Faneuil Hall in a small park are two statues of James Michael Curley. When the Irishman was elected Mayor of Boston in 1913 he declared, “The day of the Puritan has passed.” He served four terms as mayor and one term as governor of Massachusetts.

I’ve passed by these statues dozens of times and never stopped to take a closer look.

5. Maria’s Pastry Shop

Leo took pity on my frozen hands, so our first stop in the North End was a bakery. Over tea and cookies, he filled me on the neighborhood’s early history. Most people only know the North End as being dominated by Italians, but it was actually the Irish who settled there starting in the 1820s, after wealthier residents moved to Beacon Hill. The number of Irish then dramatically increased during the Great Famine of the 1840s. The Italians and Jews arrived toward the end of the 20th century, and by 1920, 90 percent of the North End was Italian – by then Jewish residents had moved out to the South and West Ends.

We also talked about more recent history, including discriminatory lending practices within the city that spurred  the Jewish migration to suburbs, and massive highway protests that took place throughout Boston in the  1960s and 1970s – North End residents had been cut off from the rest of the city when the Central Artery was built in the 1950s, leading to the neighborhood’s temporary decline.

These Italian butter cookies are just like the ones my family makes.

6. Hanover Street

Leo and I then strolled down Hanover Street, the North End’s main thoroughfare, pointing out our favorite restaurants to each other. One stop we made was at St. Stephen’s Church, since I had previously never been inside. Particularly memorable was what Leo told me after we passed a sign commemorating the site of the former Sacco and Vanzetti Defense Committee’s office – during the early 1900s the North End served as the unofficial headquarters of the Italian anarchy movement. Pro-worker and anti-capitalist, the anarchists carried out a series of bombings all over the country.

Rose Kennedy was baptized at St. Stephen’s Church. Her funeral mass was also held there in 1995.

The Madonna Della Cava Society hosts the Madonna Della Cava Festival each August to commemorate a boy’s discovery of an image of the Virgin Mary painted on a stone. It coincides with the festival that has been held for centuries in Pietraperzia, Sicily.

7. Copp’s Hill Burying Ground

We then went up to Copp’s Hill Burying Ground, the second burying ground established in Boston, where Leo pointed out the tombstones of notable Bostonians. He also showed me bullet holes on Daniel Malcolm’s tombstone, which I had never noticed before. Apparently, British soldiers, who were stationed at Copp’s Hill during the Revolutionary War, entertained themselves by using the tombstones for target practice.

Leo shows me the bullet holes on Malcolm’s tombstone.

8. Baldwin Place

Our last stop on the tour was a quick one. Leo pointed out a Star of David carved in the archway of the center building below – one of two lasting signs that the North End was once home to a Jewish community. (The other: the words “Hebrew School” are visible over a doorway on a nearby street.)

The North End’s Jewish community was concentrated along Salem Street.

What sets Context Travel tours apart from other walking tours?

Here is what I learned from my experience with Context Travel:

• Context Travel only offers personal and small-group tours (the maximum group size is six people). Travelers tend to be “culturally curious.”
• Context Travel tours are highly personalized. The guides try to tailor the information they deliver to each person’s interests, background and even political views.
• Context Travel docents are scholars and specialists – in disciplines including archaeology, art history, cuisine, urban planning, history, environmental science, and classics – who hold graduate degrees and have deep subject-area expertise.
• Context Travel recognizes travel can “build cultural bridges that foster tolerance and understanding and make the world a better place” and is committed to the principles of sustainable travel. (A part of its profits support the Deep Travel Foundation.)

Want to check out a Context Travel tour for yourself?

Context Travel operates these  Boston tours , as well as others in nearly 40 cities around the world.

Banner image: Old North Church

Thank you to Context Travel for providing me with this complimentary tour. As always, my opinions are my own .

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I still haven’t been to Boston. I love history walking tours and that bakery looks so yummy.

Boston is an amazing city (although, I admit, I’m biased because I live here). It’s packed with history, and there are lots of great places to eat too. If you ever come visit, let me know!

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A Fascinating Context Tour of Boston’s Big Dig

By: Author Lillie Marshall

Posted on Published: November 28, 2010  - Last updated: November 27, 2021

The first thing you must know is that Teachers frequently make atrocious Students.

We’re used to be the ones doing the explaining. We’re used to being in control. Our job necessitates that we move and talk constantly in order to be effective, not sit obediently and listen.

Hence, ironically, Teachers can be really annoying folks to have on the other side of a classroom.

This is to say that when a friend suggested that I check out Context Walking Seminars of my own city, Boston, I balked at first. “Whiiiine,” I whined, “But it’s my weekend! Why can’t I just sit around and do nothing?” Thank heavens I came to my senses and booked the Context Seminar… because it was great!

The concept of Context Walking Seminars is lovely: A professional scholar, specialist, and/or professor leads a very small (or upon request, private) group of “intellectually curious travelers” or locals around the hidden nooks, crannies, and little-known facts of the Great Cities of the world.

Context operates in Istanbul, Philadelphia, Madrid, and Athens, among other places. Since Boston is a Great City (woo hoo!) there are more than half a dozen different Context Seminars offered on different Beantown topics, from “Boston Brahmins,” to the Museum of Fine Arts, to the North End. Since I have a giant Big Dig fetish (more on this later), I lustfully enrolled in the Big Dig seminar. Exciting! (I also love the concept of context in general, so click to learn more about that word.)

Here was my vividly-imagined prediction of how the Walking Seminar would go: We would all don thick protective jumpsuits and dive down into a secret pipe (akin to those in Mario Brothers, with the same “shh-shh” sound effects) which would shoot us deep into the bowels of the Big Dig itself.

I pictured our tour being stopped by a Big Dig policeman (with dark circles under his underground-accustomed eyes), who would bark: “What are you doing down here? NO ONE is allowed down here!” Then we would all take out secret Context badges, which would cause the guard to jump, bow reverentially, then say, “My mistake! Enter into the secret tunnels behind the main tunnel, oh intellectually curious voyagers!”

But that’s not what happened.

In fact, there was no underground spelunking element to our tour at all. And that was just fine, because I was wearing a new sweater and didn’t want any gloop from secret pipes on it.

The name of the Context Tours company does not lie: It’s all about CONTEXT.

“What exactly is “Context,” again?” you may be asking. Well, if you are a lucky duck who is in my English class, you would know there’s a little dance we do to illustrate what Context is: Wave your arms up, down, left and right (preferably with jazz hands)! What this means is that “Context” entails all the juicy details that surround something, be it the sentences that surround a difficult vocabulary word, the time period in which a particular novel was written, or, in the case of the Boston Walking Seminar, the facts, buildings, and historical progression surrounding the creation of the Big Dig itself.

At 9:30am on the appointed Saturday, I showed up under the awning of a certain bagel shop in Downtown Boston to meet my gang for the day. Coolness: it was just me, three other friendly New Englanders, and the extremely amiable, knowledgeable Docent. True to Context’s ethos, our Docent turned out to be a bona fide Professor of Architecture who had done googobs of research on Big Dig-related topics in her illustrious career.

We introduced ourselves, and then our Docent took out a thick folder of goodies to kick off our Context-izing… most notably, the map shown here to the right.

Really take a moment to study this diagram and understand what it means. When you got it, did your brain just explode?! It shows how all that light gray part of Boston on the map (Back Bay, South Bay, East Boston, a bunch of Cambridge, etc.) used to be swamp or underwater! Then hard-working folks after 1630 leveled the hills in town and painstakingly placed that dirt in the water to create the land we now dance around today.

WHAT?! That is AMAZING! Truly take a moment to honor that accomplishment. Let’s not take for granted the paths beneath our feet, Bostonians!

Our Docent then pointed on the map to the tiny neck of original land between the round bulb of Boston proper and the mainland. “Can you guess which street stretched down that narrow piece of earth?” she asked. We looked around us, as we knew the answer must lie near.

“Washington Street!” we realized. Indeed, think about how central Washington Street is in connecting Boston. It has an extra special place in my heart this year, especially, as I now commute right down it each day on the Silver Line between Downtown and Dudley Station. It’s a thrill to realize how the past shaped the present!

Our Docent then pointed back to the map. “Notice,” she said, “how, back in the day, there was no land connection between South Station and North Station.”

We nodded, and remarked that today there may be a land connection, but there is STILL no rail link between the two.

“Keep that in mind,” our Docent said, “because this desire for a South-North Station link is behind much of the subsequent development of Boston, right up until the Big Dig.”

On the map, our Docent then pointed out several more cool tidbits. First, though people joke that Boston was laid out by cows, if you really look at the history and topography of our cities, you will note that the winding (a.k.a. confusing, a.k.a. ridiculous) street patterns trace back to paths that ran around the hills: hills which no longer exist because they were leveled in order to fill in the swamps and create the land we now take for granted!

Second, ever since Washington Street was the only connector between Downtown Boston and the mainland, we Bostonians have had too many people to transport in too small a space! It’s our heritage, and innovations to address it have been on our mind for centuries. (Literature-loving students, can you see some foreshadowing for the Central Artery and then the Big Dig???)

We began to walk. First, our Docent pointed our attention to the second building shown in this article, followed by the lovely Old City Hall (not to be confused with the brutal New City Hall ) down the street. She explained that these early buildings still really reflected European architectural influences, as America had yet to really develop its own distinct identity. (Ahh, those awkward teen years.)

As we continued along, however, and the “vintage” of the buildings became newer, America’s architectural voice began to emerge. Our Docent took us right up to one of her favorite buildings: The Winthrop Building (pictured to the right) which is one of the earliest examples of steel architecture in history! Building with steel was essential because in the 1800s, cities had frequent fires, and steel has the benefit of not melting so easily (and no one likes a melted building).

Our group stood by the Winthrop Building for quite a time, admiring the fact that it’s curved instead of straight (!), ogling the jaunty green, red, and yellow pattern, and cooing over the delightful green, circular decorations under each window. (Speaking of green, don’t forget Boston’s Emerald Necklace parks .) Our Docent explained that steel construction allowed a whole new realm of architectural expression distinct from European heritage. Check it out: I’ve lived in this city my whole life and passed this building a zillion times, but I’ve never even noticed it, let alone had a hint of its significance!

Onward, to the Ames Building (pictured to the left): another structure I’ve never given a second glance to! Turns out that the Ames Building was Boston’s first “skyscraper” (sounds crazy now, that that little thing could seem to scrape the sky, right?), and remained the tallest building in our town from 1893 to 1915.

Our Docent breathily showed us how the architect had crafted the building: to “stop the eye:” breaking it up artistically into levels and parts, much like a giant-sized column with mini-columns within it. “From afar,” our Guide explained, “you may not be able to see the details, but you do certainly see the lovely dance of light and shadow!”

Truthfully, I never before saw that dance on that building… but now I sure will!

At this point, as I write this, my bus from Philadelphia to Boston is in hour three of being broken down by the side of the highway. It’s getting cold in this bus, and a little stinky. I’m laughing, thinking how, for all our American innovation and progress, we still have a long way to go! Oh, “Developed World…” you’re giving me flashbacks of my bus breakdown in Thailand, and my 30-hour bus from Vietnam to Laos.

And thus at this point I shall pause this Context Walking Seminars tale mid-way to warm my hands and stretch. Stay tuned as we move from Downtown towards the Big Dig site, scooping up context and fascinating historical facts along the way!

See a tour and details of Boston Black history here.

The author, Lillie Marshall, is a 6-foot-tall National Board Certified Teacher of English, fitness fan, and mother of two who has been a public school educator since 2003. She launched Around the World “L” Travel and Life Blog in 2009, and over 4.2 million readers have now visited this site. Lillie also runs TeachingTraveling.com and DrawingsOf.com. Subscribe to her monthly newsletter, and follow @WorldLillie on social media!

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Sunday 30th of January 2011

amazing! I will start seeing Boston differently now with this little lesson on architecture... hell! i'll see American cities differently, including Providence, now that I know these facts about American cities. very enlightening article :)

Woo hoo! Thanks! The craziest part to me is still the fact that we were mostly swamp before the landfill fun. Keep your comments coming :)

Kevin Armstrong

Wednesday 22nd of December 2010

Wow I never knew that Boston was part landfill. I still love Boston very much though.

Daniel Rodriguez

Tuesday 14th of December 2010

Very informative and fantastic enthusiasm!! I've had an experience also relating to the police officer in the Big Dig site at my job. Reason being that I'm a fairly young person to be working in Harvard, so the first few times i went to work i was asked for my I.D. ten they would apologize for the inconvenience. Anyways, I loved the article and I second Drew's remark on the fact that Boston has many places and elements of Boston that make it so awesome!

Tweets that mention A Fascinating Context Tour of Boston’s Big Dig, Part 1 | Around the World "L"! -- Topsy.com

Tuesday 30th of November 2010

[...] This post was mentioned on Twitter by contexttravel and Context Travel USA, Context Travel USA. Context Travel USA said: @WorldLillie We were delighted to have you! RT @contextusa Thanks for a great #Boston Walking Seminar! Story: http://tinyurl.com/3x3pux6 [...]

Monday 29th of November 2010

I saw a diagram similar to the one above in the Hancock Building years ago. I vaguely remember the landfill expansion evolving over the years. I also remember that corridor of land still being relatively small during the Revolution. The history of Boston's expansion is one of the many things that make Boston as unique as it is.

The Perfect 2, 3 or 4 Days in Boston Itinerary

Last Updated on January 29, 2024

by Audrey Webster

Disclaimer: This article contains affiliate links. That means if you click a link and make a purchase, we may make a small commission. As an Amazon Associate we earn from qualifying purchases. For more information, see our privacy policy.

As one of the oldest cities in the country, Boston is filled with history. It’s a mash-up of cobblestoned streets and historic buildings with modern skyscrapers. There are a few places you cannot miss while spending a few days in Boston, as well as some lesser-known parts of the city we’ll cover here.

As one of the most dynamic and historic cities in the country, there is a lot to do in Boston and so much that you can’t miss. From American history to esteemed universities to excellent museums and fantastic food (there’s more than clam chowder!), Boston has something to offer everyone.

Table of Contents

How Many Days in Boston?

When in the initial stages of planning a trip, many do wonder how many days to spend in Boston in order to do this New England city justice.

With 2 days in Boston, you’re just scratching the surface. Most of the city’s main attractions are clustered together, so you could see a lot in 2 days, but you’re also missing out on some cool parts that make the city unique.

If you have 3 days, you’re in good shape to see all the highlights as well as some lesser-known sites. You’ll be able to strike a balance between visiting historic landmarks and more trendy neighborhoods.

If you’re lucky enough to have 4 days, you can see more of the city at your leisure or use the fourth day to take a day trip to somewhere nearby. There is no shortage of historic sites and beautiful nature just outside Boston. 

Getting To & Around Boston 

You’re most likely arriving in Boston through the Logan International Airport. You can easily hail a cab, take the GO Boston Shuttle, pre-book a transfer or use public transportation to reach downtown.

If you’re visiting from another city or town in New England or even some city further south such as Washington DC or New York , you might arrive on a train or bus. Make sure to find out which train or bus transfers you need to make depending on where you’re coming from. You can view schedules here.

The Massachusetts capital is a very walkable city and it’s not actually that big. In fact, one of the best things to do in Boston is walk the Freedom Trail. Many of the most historic landmarks are located near each other.

Boston is also well-connected via a subway system, known locally as the T. You can easily get around the city using this if you want to reach somewhere a bit further afield.

Alternatively, there is the Hop On/Hop Off Trolley Tour that provides a convenient way to see the city. Taxis and rideshare are both readily available as well. It is also included in the Boston Go City Pass , which will also save you on entrance fees to many of the paid attractions listed here.

2, 3 or 4-Day Boston Itinerary

If you’re spending a few days in the Massachusetts capital, then there are a number of guided tours that you can take to get an overview of the city such as this historical walking tour , this bike tour or this food tour.

Day 1 – Freedom Trail, Museums, Quincy Market & More

Walk the freedom trail.

This 2.5-mile trail covers many of the historical highlights in Boston. You’ll want to dedicate a few solid hours to walking the trail. You can opt to walk the entire thing or a portion of it.

There are also guided tours available such as this 2-hour walking tour , which could be helpful for providing context to the landmarks as you pass them. Here are the landmarks you can expect to see:

• Boston Common & Boston Public Garden
• Massachusetts State House
• Park Street Church
• Granary Burying Grounds
• Boston Latin School/Benjamin Franklin Statue
• Old South Meeting House
• Old State House
• Faneuil Hall
• Site of the Boston Massacre

Paul Revere House

• Old North Church
• USS Constitution
• Bunker Hill Monument

You could spend however long you’d like walking the Freedom Trail and note that it doesn’t cost anything to walk the trail, but there are generally entrance fees for the various sites.

Depending on how long you want to spend, take the time to walk by these places and pick one or two that interest you to plan to visit those places. With that in mind, plan to spend 2-3 hours on the Freedom Trail.

Boston Tea Party & Ships Museum

Veer off Freedom Trail just slightly to pay a visit to the Boston Tea Party and Ships Museum.

The museum is chock-full with historical experts, interactive exhibits, full-scale replica sailing vessels, and historic artefacts to make this monumental event in America’s history come to life. You can pre-book tickets here.

If you have some time to spare, you can watch an award-winning documentary in Minutemen Theatre that depicts the events that led up to the American Revolution. 

Next to the museum, don’t miss the Observation Deck at Independence Wharf, either, where you can get excellent views of the harbor.

Quincy Market

Quincy Market is where old and new seamlessly merge. Here you can find hundreds of shops, both inside and outside the building. The market was established in 1825 and spans three buildings: Quincy Market, South Market, and North Market.

It’s another great place to stop as you’re walking the Freedom Trail to grab a bite to eat or do some souvenir shopping. The market is especially charming during the winter months when it’s decorated for the holidays. Quincy Market was named a National Historic Landmark in 1966. 

Go to a Red Sox game

Go see the “Green Monster” for yourself during your visit to Boston. Even those who wouldn’t consider themselves baseball fans will enjoy seeing a game at Fenway Park.

It’s been the home of the Boston Red Sox since 1912, making it the oldest stadium in Major League Baseball. If you don’t have time to see a game, you can still take a guided tour of Fenway. It’s a great way to wrap up your first day of sightseeing in Boston. 

If it’s not the season for baseball or you don’t care to go to a game, then use this time to stroll along the Charles River Esplanade or, perhaps, visit the nearby Boston Museum of Fine Arts. You could also simply relax in the tranquil surroundings of Back Bay Fens Park.

Day 2 – Boston’s Museums

John f. kennedy presidential museum & library .

This exceptional museum is dedicated to the life and accomplishments of U.S. President John F. Kennedy.

Here, you’ll wander the permanent exhibit that uses large-screen projections, interactive displays, original artefacts, and re-mastered films to learn more about the former president’s life. Consider reserving tickets online in advance to save you time at the door. You can also opt for a guided tour.

A visit to the JFK Presidential Museum & Library is a great way to kick off your second day. 

Institute of Contemporary Art

If you have 2 days, you should consider visiting one of the many local museums. A city that’s so full of history has some great historical museums, but it also has notable art museums like the Institute of Contemporary Art.

Here you’ll find both permanent and rotating exhibits featuring contemporary artists and their work. The museum is located in a beautiful building on the waterfront overlooking Boston Harbor, so you can also take in the view. It’s recommended that you book tickets in advance. 

Isabella Stewart Gardner Museum

This museum is known for its beautiful architecture and courtyard garden. It’s a great museum to visit if you want one that is a little less crowded than other larger museums in the city. Beginning in the late 1800s, Isabella started collecting rare books, manuscripts, and pieces of art to fill her home.

Over the course of her worldwide travels, she acquired art like Rembrandt’s Self Portrait and Titian’s Europa. The museum as it stands today was built in 1901. She lived on the fourth floor and spent the remainder of her life arranging the art throughout its halls.

It’s a unique museum that’s a quiet way to spend the afternoon. If this or any of the other museums don’t interest you, there are plenty of other museums in Boston to take in. For instance, the Museum of Science – located in a building overlooking the Charles River, is an excellent place to visit if you happen to be traveling with children.

Day 3 – Boston Common, Trinity Church, Paul Revere House & More

Boston common.

You might’ve already passed through Boston Common if you walked the entirety of the Freedom Trail. If you didn’t stop for long then, it’s worth your time to dedicate a couple hours to really enjoying the park. Boston Common is America’s oldest public park having been established in 1634 and is located in the Beacon Hill neighbourhood of Boston.

Today, the park is filled with fountains, picnic tables, and green spaces for visitors to lounge and enjoy the day. Make sure to stroll through the adjacent Public Garden, as well, to truly enjoy this urban green space. If you’re seeing Boston in 3 days, then a visit to Boston Common is a great idea.

Trinity Church

When you start exploring Boston, you’ll immediately notice Trinity Church in Copley Square. This historic stone church sits squarely in the middle of downtown’s towering skyscrapers. It’s considered by the American Association of Architects as one of the top 10 buildings in the country.

The parish located there today was founded in 1733, which is more than 150 years before the church was built in 1877. You can enter Trinity Church on your own or schedule a tour with a knowledgeable tour guide to learn more about the church’s history. 

It looks striking as it’s sandwiched between modern skyscrapers like the John Hancock Tower and the Prudential Tower and really symbolises Boston’s mingling of old and new.

Located in the North End neighborhood, the Paul Revere House was the former home of the famous Founding Father Paul Revere. He played a pivotal role in the American Revolution, noted in history books for his famous “midnight ride” to warn colonists that the British were approaching Boston.

The home was built in 1680 and is downtown Boston’s oldest building. Inside, the home is set up to mimic what it would have looked like while Revere lived there. In fact, 90% of the structure today is original material, including doors, windows, flooring, and internal wall material.

You can pop into this Boston museum for a self-guided tour or try to time your visit to see colonial reenactors demonstrate key moments of America’s history. 

If this doesn’t interest you as much or if you’re traveling with children, consider, as well, heading to the nearby New England Aquarium where you can learn all about local marine life or you can take a food tour of North End.

The Museum of Bad Art

You’ve probably never been to a museum that focuses on bad art. The Museum of Bad Art houses “art too bad to be ignored” and is a highlight worth adding to your time in Boston. It’s the world’s only museum dedicated to bad art that began in the basement of a private home.

The museum has since grown into a local favorite that shines the spotlight on quality bad art. It’s a quirky and fun addition to your Boston trip, especially if you happen to be planning a 3-day itinerary. 

Day 4 – Lexington & Concord, Salem or Cape Cod Day Trip

Lexington and concord.

Lexington and Concord is arguably the most famous site of the Revolutionary War. For history buffs, this is a great way to round out your 4 days in Boston. It’s where the first shots of the war were fired.

To reach Lexington, you’ll take the subway and bus for a total travel time of about 45 minutes before getting off at Lexington Battle Green. You can reach Concord by taking the MBTA directly from Boston.

Lexington Green is a good starting point for your visit. This small town is home to the Belfry that sounded the alarm in 1775 to call the militia to fight. Here, you’ll also find John Hancock’s childhood home or Buckman’s Tavern. In Concord, make sure you visit the Old North Bridge.

You can also find Walden Pond, made famous by writer Henry Thoreau, and Louisa May Alcott’s “Orchard House”. There’s a lot to see during a day trip to Lexington and Concord, so make sure you leave early in the day to give yourself ample time. 

You’ve most likely heard of Salem, Massachusetts due to its famous 1692 witch trials. Salem is only about 30 minutes from Boston, so it’s an easy day trip. You can easily reach it by taking the commuter train that connects the cities, a high-speed ferry or an organised day tour.

During your day in Salem, make sure to visit the Salem Witch Trials Memorial, Peabody Essex Museum, the Old Town Hall, and the Witch House. You can end your day with a visit to Winter Island Park and Lighthouse.

As you might’ve guessed, one of the best times of year to visit Salem is Halloween. The little town comes to life with spooky decorations.

Without a doubt, Cape Cod is beautiful, especially in summer. This stretch of coastline is full of charming towns, great seafood, and relaxing beaches.

Cape Cod is about 3 hours from Boston by car, which tends to be a little long for a day trip. Instead, you can take the Cape Cod Fast Ferry from Boston to Provincetown, which is the largest town on the Cape.

In Provincetown, you can enjoy the local art galleries, lounge on the beach, and walk around and enjoy the quaint homes and shops.

If you have more than 4 days in your Boston itinerary, spending more than one day on the Cape is a relaxing way to bring your time in the area to a close.

Where to Stay in Boston

Harborside Inn – This 3-star hotel in downtown Boston is a great choice for mid-range travelers to the Massachusetts capital. There are a number of great rooms to choose from, a wonderful location for exploring the city and plenty of other amenities to enjoy.

Omni Boston Hotel – If you’re looking for luxury while in Boston, then this sophisticated hotel is a great option. They have a range of lovely rooms on offer and an unbeatable location for exploring all this historic city has to offer.

HI Boston – Those visiting Boston on a budget will love this backpacker’s hostel in the center of the city. They have a range of both dorms and private rooms on offer along with other perks and great common areas for guests to enjoy.

Not quite what you’re looking for? Click here to browse more Boston hotels!

The perfect itinerary for Boston is the one that’s packed with what excites you most. If you’re a history buff, you’re going to love it here. Foodies, explorers, and everyone in between will find something to love in Boston.

Are you planning a trip to Boston? Have any questions about this itinerary? Let us know in the comments!

Related Posts:

17 Best Stops on a Boston to Bar Harbor Road Trip

The Perfect 2, 3 or 4 Days in Cape Cod Itinerary

Martha’s Vineyard vs Nantucket: Which Island to Visit?

About Audrey Webster

Audrey Webster is a writer for The World Was Here First. She is an Oregon native who has visited countries across the globe and currently spends her weekends exploring the Pacific Northwest and surrounding states. Her approach to traveling combines exploring famous tourist sites and wandering off the beaten path to discover new destinations.

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Thirdeyemom

Traveling the world and doing good, context travel: small guided tours for the intellectually curious traveler.

At the end of May, I attended my third TBEX conference (Travel Blog Exchange)  and was introduced to Paul Bennett and his wife Lani, the founders of Context Travel . Context Travel is a network of Ph-D level scholars and experts living in cultural capitals around the world who take tourists on small or private guided tours of their cities. Paul and Lani founded the company in 2003 after two years of sailing across the Atlantic with their young children. They were so inspired by the experiences while traveling that they wanted to create something authentic and unique. A kind of travel company that would enable travelers to get a rare behind the scenes view of what a place is like while also promoting sustainable travel. There are no tour buses or tour guides; instead you are swept away on a walking “seminar” with a local expert.

The Context vision is to create an atmosphere—a context, if you will—for curious travelers to engage with local experts; to give them access to places and cultures that might otherwise remain out of sight to the casual visitor; to invite them off the tourist track and into the real life of the people, history, and culture that makes these cultural capitals amazing.

Paul and Italo on a drive through Venice’s canals.

Fast forward 13 years, and Context Travel now operates in over 35 cities around the world, inspiring travelers to see a city through local, knowledgeable eyes. Context Travel is recommended by such acclaimed sources as the New York Times , Travel and Leisure , and National Geographic (to name a few)  as well as a growing number of highly satisfied customers. I was so inspired by Paul and Lani’s story that I asked to do an interview to learn more. Here is what Paul had to say.

Where did you and Lani meet?   Lani and I met at Macalester College in Existentialism class. Seriously.

What did you study in college?   We both majored in English.

Did you both travel internationally before starting Context Travel?   A little. We both did post-college trips through Europe and some basic Caribbean and Mexico travel. I worked as a journalist for several years, and that took us to places like Rome and Ecuador. Just before we started Context we sailed a 38-foot boat from New York to Italy via Central America, on a voyage that took nearly 2 years and included stops in places like the Azores (highly recommended).

Where was your first trip?  My first international trip was as a teenager. I went on a school trip to China in 1987. It blew my mind.

What inspired you to start Context Travel?  When we arrived in Italy after sailing for two years we realized that the single most important ingredient to our travels was being able to connect with some local expert who some kind of specialized knowledge of the place and could get us access beyond what we could glean from a guidebook. For example, in the Azores I had an assignment for Islands magazine to interview a master scrimshaw artist. This guy was amazing and taught us so much about the heritage of whaling in the islands—much more powerful than what we got from Lonely Planet. And so this became the impetus for Context: To connect curious travelers with local experts when they arrive in destination.

When did you start Context Travel and in what country?  We started in Rome in 2003.

What has been the most challenging part of starting and running the business   Geez. Everything. Bootstrapping a business requires wearing a lot of hats. We’ve had to become effective recruiters, storytellers, financial managers, digital marketers… and so on. Getting technology right has been our biggest struggle.

What has been the biggest reward?  The quality of what we do. There’s a common arc among Context experiences. It goes like this. A traveler finds us, perhaps through a post like this. They come to our website and compare us to other companies and usually pick a Context tour because it seems like the best quality. Maybe they like the credentials of our docents, who mostly have Ph.D.s. Or, maybe they like the small group size (6 max). Whatever. But, they show up at the tour thinking that it will be a good tour. Three hours later they are amazed. We’ve completely changed their thinking about art, history, or heritage, and given them a much deeper travel experience than they expected. They’re transformed. Hearing this story day in and day out is the biggest reward.

What makes your tours different from others on the market today?   Small groups, expert docents, and a commitment to creating immersive experiences.

Context New York MOMA Seminar, led by art historian Ara Merjian

Give me a few examples of what visitors will experience on one of your tours?  In Paris one of my favorite tours is  Immigration and the Changing Face of Paris , which is led by a local sociologist and explores the history and present situation of Arabs and North Africans in France. We visit some neighborhoods that most tourists never see, and talk about the headlines. But, because the guide is actually a specialist in this area with a degree in sociology, you get a much deeper, more nuanced approach than what you read in the media.

I also love our  Birth of the Cocktail  walk in New York, which looks at the history of American cocktail making from Prohibition through the speakeasy revival movement of the early 2000s. The drinks are good, but the narrative is even better.

In Asia, I’m crazy for our  Anime and Manga  walk in Tokyo. It’s just super cool.

Of course, we also do the  Louvre ,  the Vatican , and the  Tower of London ; and those are pretty mind-blowing, especially in a small group with a highly knowledgeable, Ph.D.-level docent.

Where are your tours offered?   Rome, Florence, Venice, Milan, Tuscany, Naples, Paris, Barcelona, Madrid, London, Dublin, Edinburgh, Amsterdam, Berlin, Prague, Vienne, Budapest, Athens, Istanbul, Bangkok, Hong Kong, Shanghai, Beijing, Tokyo, Kyoto, Melbourne, Sydney, Buenos Aires, Rio de Janeiro, Cartagena, Washington D.C., Philadelphia, New York, Boston, Montreal and Vancouver.

Tell me about the guides. How do you find them and what kinds of backgrounds/expertise do they have?   In academic subjects we look for people with a Ph.D. in the topic and some experience teaching. In non academic topics we look for experience in the field—practicing architect, chef, e.g. During the interview process we test their ability to craft a narrative and tell a story. We also look at their emotional intelligence and whether they will be the consummate host. We have a bunch of training designed around this.

How long do tours run and how much do they cost?  3 hours is our sweet spot, and the average price is $90 pp for a group walk or about $350 flat fee for a private walk.

What have past participants said about your tours?

“Our tour was fabulous. Our docent knew the history and food of Barcelona and her knowledge was unbelievable. ”

“ Amazing, simply amazing. 10 out of 10!”

“Be careful. Once you’ve taken a Context tour you’ll be spoiled. Not only will you never want to use any other tour company, but you’ll be very hesitant to visit any city where Context doesn’t offer their services. It’s that good.”

Where do you hope to see Context Travel in the next ten years?   I see us operating in 100 cities and known as THE tour company for the culturally curious.

Finally, tell me more about your sustainability practice and why it is important.  This is really baked into our DNA. We run a nonprofit that supports local initiative like a scholarship program for apprentice artisans in Florence and a youth center in Cartagena. Our docents are trained to talk about sustainable travel practices like flashes in museums and how to invest your travel dollars wisely with local businesses.

About Paul and Lani, founders of Context Travel

Lani Bevacqua, Paul Bennett and one of their children, Jade.

Paul spent the first part of his career as an award-winning writer for National Geographic and National Geographic Adventure. He holds an MA from St. John’s “Great Books” program and has written four books for Princeton Architectural Press about architecture and landscape. He founded Context with life/business partner, Lani Bevacqua, in 2003 after having spent 18 months sailing a 38-foot boat from New York to Rome.

Paul oversees strategy, finance, and bad jokes. When he is not helping run Context, Paul lectures on travel and sustainability, and works on the Context Foundation for Sustainable Travel.

Lani co-founded Context with life/business partner, Paul Bennett, after having sailed to Rome from New York on a small boat. That experience deeply informs everything she does at Context.

In a previous life Lani was a graphic designer and art director in New York City. She worked in-house for Artforum, Dance Theater Workshop, and Gartner Group. Her agency clients included Gillette, Compaq, Computer Associates, IBM, and PeoplePC. She won awards for her digital advertising and web animation. Along with being the creative director and designer for the Context websites and publications, she is home-schooling three small children and is the impetus behind Context’s much-lauded Family Program.

About Context Travel’s sustainable tourism and social responsibility commitment

Context adheres to the precepts of sustainable travel. We invest in programs that mitigate the effect of tourism.  Learn about the Context Foundation for Sustainable Travel.  Context is also a certified B Corporation. B Corporations are a new kind of company which uses the power of business to solve social and environmental problems. Learn more about  B Corporations .

To learn more about Context Travel and their tours, visit their website here.

I would love it if you shared!

30 comments.

very interesting. would love to pitch in as no Indian city on the List.

Feel free to contact them via their website!

will do, tks.

This sounds awesome, something I’d love to get involved in

Yes it is fantastic!

You know, I’ve thought of doing some posts like this, but just don’t seem to get around to it. This is a nice diversion, and interesting concept for travel. I might look them up! Or get a job!

Thanks! I like to mix it up a bit on the blog and also provide information that readers will find useful especially since many travel.

Sounds like a great way to travel.

They have the tours in DC and I am going to do one next time I visit. The tours sound amazing! I love to learn and I’m sure the DC tour would teach me things I don’t know .

Interesting concept. My parents used to travel with Elder Hostel which sounds like a similar idea and tgey too loved it. The problem I have with organised activities is the stickng to a schedule which I sm not very good at doing, especially when travellng.

That sounds cool too! The great thing is these are short so it isn’t too much of a commitment.

These are great, thanks for sharing! Just booked a spot on a Marquez tour in Cartagena, Colombia for my upcoming trip 🙂

Wonderful! I would love to hear back on how it went! If you remember can you let me know? I’m hoping to do one in DC or NYC next time I’m there. Cartagena sounds fabulous!

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Thank you for sharing more about this organization — I’m definitely going to look them up!

You’re welcome! If you do a tour with them, let me know. I would love to hear how it goes. 🙂

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Fantastic idea! it makes such a huge difference to see a place through the eyes of someone who is not just selling you the standard tourist-y facts & figures

Yes I imagine the tours are amazing. I am hoping to do one soon when I travel.

I love the idea of a more intimate tour, especially from a locals perspective! Next time I visit a new city I’ll have to look these guys up. Sounds like something special

Yes me too. It is a wonderful concept and a much different perspective to regular tours. 🙂

Great article! I’ve been all over the world and it makes so much sense to try and “live like a local” when in foreign places. Have you been to Napa Valley, California? Check out and follow our wine country blog: http://www.topochinesvino.com .

Thank you and will do!

I love the idea of going on an in-depth tour of a single subject in a city to help gain new perspective and understanding of it. I’ve been on a few tours, one in Europe, which was great but very need-to-know basic. Then, in South Africa, we had locals who took us through some spots and it made a difference in hearing their stories and perspectives to add more context. I’ll have to try to check one out next time I travel to one of their cities.

Thanks so much for the comment! Yes local guides and tours are always the best. I always learn so much more about a place.

I absolutely love Context Travel. I have been in touch with Paul and would love to work with them some day. I have pitched so many of their tours to my Indian clients, but unfortunately do find them very steep as they do not see the value. I shall not quit though. I have recently pitched their Tokyo & Kyoto walks. Fingers crossed!

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- Jane, Traveled in Rome with Dimo in Sept. 2021

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