Top 10 Tours in Boston, Massachusetts (MA)

May 14, 2022 Sachiko Swiger

Walk the Freedom Trail the first time you visit Boston and you'll quickly get a sense of this coastal city's revolutionary spirit and history. But make sure you also explore some of Boston's fine museums (try the Isabella Stewart Gardner, featuring masterpieces displayed in their collector's mansion) and old neighborhoods (like the North End, Boston's Little Italy). You can't claim to have experienced real Boston culture, though, until you've watched a Red Sox game from the bleachers.
Restaurants in Boston

1. Boston's North End Pizza & Cannoli Small-Group History Walking Tour

Tony DeMarco Statue, 191 Hanover St, Boston, MA 02113, USA
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5.0 based on 2 reviews

GOT PIZZA? Discover the North End on a Food Tour through Boston's Little Italy. There are hundreds of pizzerias in Boston, and the North End alone has more than 50 different pizza sellers. Stops on tour rotate, but may include a Sicilian slice that a famous Food Writer named #19 on his "Top-25 Best slices in America" list, or Neapolitan-style from the pizzeria that won "Best at Fest" at Boston's 1st annual pizza festival, or a slice that TripAdvisor reviewers named "Best Slice in America " back in 2018. Every Pizza Tour ends with cannoli from a famous North End bakery!

Inclusions: Includes three different (award-winning!) pizza slices., Bottled water, Every tour finishes with a cannoli from a famous North End bakery!, See five Freedom Trail sites

Exclusions: Tip / Gratuity for your hardworking Tour Guide is not included.

2. Small-Group Boston Lobster Lovers Walking Tour with Dessert

Tony DeMarco Statue, 191 Hanover St, Boston, MA 02113, USA
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5.0 based on 2 reviews

This Fun & Educational Food Tour combines Boston's rich Colonial & Revolutionary history, with some of the City's most iconic Seafood. Stroll along Boston's scenic Harbor Walk as we learn about historical sites like the Paul Revere House, Long Wharf, Faneuil Hall and the Old State House. Enjoy Seafood favorites like Lobster Mac & Cheese, Lobster Bisque, Lobster Roll and finish with a treat from a famous North End bakery!

Inclusions: Enjoy iconic Boston Seafood favorites like Lobster Bisque, Lobster Ravioli and Lobster Roll, plus a Lobster Tail (cream filled Italian pastry) for dessert., Bottled water, Taste a Lobster Tail (cream filled Italian pastry) for dessert, at a famous North End bakery!

Exclusions: A Tip / Gratuity for your guide is not included.

3. 90-Minute Ghosts of Boston Tour

58 Tremont St, Boston, MA 02108, USA Ghost City Tours
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5.0 based on 5 reviews

Our Ghosts of Boston Tour takes you on a journey to meet the ghosts of Boston, Massachusetts. You'll visit haunted houses, cemeteries where ghosts are seen, and much more on this Ghost Tour The Ghosts of Boston Tour focuses on the Patriots who helped make America the country we are. We'll visit many historic locations which are tied to the founding of America, the Revolutionary War, and more. The Ghosts of Boston Tour puts history front and center - but in an entertaining and engaging way You may have seen some of the locations we visit on this tour on TV shows like Ghost Hunters and Ghost Adventures

Inclusions: All Fees and Taxes

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Reviewed By kikipuff99

This tour was a waste of money. The tour guide was horrible at telling stories, it was hard to follow his train of thought, and worst of all, it wasn't even interesting or spooky. I knew we weren't going to see ghosts, but this should not be advertised as a ghost tour. It is a history lesson about the area from a tour guide who didn't know his history. Wish I could get my money back

4. The Revolutionary Story Tour

1 City Hall Square, Boston, MA 02201, USA The Revolutionary Story Tour
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5.0 based on 217 reviews

What makes this tour different is that instead of walking the Freedom Trail geographically – starting at one end and following it to the other – we let the escalating action of the American Revolution guide us through the crooked streets of Boston. The sightseeing is synchronized with and unfolds to the storytelling. There’s a lot less emphasis on dry facts and dates and a lot more on the passions, personalities, and psychologies driving the events; recreating the drama and recapturing the energy that invented America. It's not only much more enjoyable it's also the most effective way to explore the city and relive the history. The entire experience has been built with the aspirations and anxieties of a fellow tourist in mind: the groups are kept small so you aren't herded around; we cover both the major sights and the hidden gems; extensive visual aids and props help you grasp the material, and you'll traverse all original neighborhoods getting a sense of the modern city as well. 

Inclusions: Limited group size. No massive crowds., Professionally operated: no actors, costumes, scripts, or kitsch, Insights from prestigious historians and scholarship, Restroom / Coffee / Snack break midway through, 12 (of 15) Freedom Trail sights visited

Exclusions: Gratuities. (optional)

Reviewed By Roman R

Incedible Tour of the history of Boston and the American Revolution. Recommend it to everyone coming to Boston.

5. Boston Small-Group Food & History North End Freedom Trail Walking Tour

222 State St, Boston, MA 02109, USA Boston Urban Adventures
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4.9 based on 208 reviews

Discover the local side of Boston’s most popular neighborhood, the North End.  Visit Boston’s most revered church and snack your way through the neighborhood, tasting meats, cheeses, fresh bread, pastries, pizza and cappuccino.  Continue along the Freedom Trail and beyond and experience modern Boston through the city’s incredible history.  From the iconic Boston Harbor,  into the heart of beautiful Beacon Hill, join your local guide on an experience that connects you to the Boston of old and new.

Inclusions: Local English-speaking guide, A variety of food samples such as fresh bread, pizza, and pastries, Entrance fee to the historic church (or equivalent alternative), A surprise local treat

Exclusions: Tips/gratuities for your guide

Reviewed By Explorer23589041516

I don't like writing reviews like this but I need to be honest... this was the worst food tour I have ever been on. I have been on several in different cities and some were stronger on the food aspect and some were stronger on the historical aspect. This was very weak on both. The guide was nice and when she spoke it was informative, but, like the food, it was not even close to enough. From the food aspect, there felt like there was very little coordination with the venues we visited. At 2 of the locations we waited about 30 minutes for our food (no one seemed to call ahead, etc.). We only sat at one venue, which was a great stop on the tour - we had an authentic cannoli and outstanding cappuccino. Other than that, our food consisted of 2" of bread, 3" of an Italian sub, and a slice of pizza. During that time of waiting I had wished for much more information to be dispensed. Based on the other ratings and comments from other folks, perhaps this was just a bad day(?) If that is the case, then I wish we had attended on a better day.

6. Boston History & Highlights Small Group Walking Tour

222 State St, Boston, MA 02109, USA Boston Urban Adventures
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4.9 based on 94 reviews

Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history.  From the iconic Boston Harbor, to the famous Freedom Trail, into the heart of beautiful Beacon Hill, join your local guide on an experience that promises to connect you to the Boston of old and new.

Inclusions: Local English-speaking guide, A surprise local treat

Exclusions: Additional food and drink, Souvenirs, Tips/gratuities for your guide

Reviewed By LarryGNewYork

I have been to Boston many times, but this tour was as if I had landed in a completely different city with it’s Italian charm fused together with American history. Our tour guide Bob made the journey especially fun, as well as educational, but he was no match for the mouth-watering food around every corner and alleyway. Here’s to the Red, White and Blue!…as in blew me away. Viva Italia!

7. Boston's North End Small-Group Walking Food Tour

222 State St, Boston, MA 02109, USA Boston Urban Adventures
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4.9 based on 122 reviews

Discover the local side of Boston’s most popular neighborhood, the North End. Visit Boston’s most revered church and snack your way through the neighborhood with delicious tastings of meat, cheese, bread, pastries, pizza, and cappuccino.  Tradition, history and food define the North End, so join us to discover the best of this dynamic neighborhood and we’ll taking you off the beaten path to discover some of our favorite hidden gems too!

Inclusions: Local English-speaking guide, a variety of food samples such as fresh bread, pizza, meats and cheeses..., ...pastries and a hot drink, , plus the entrance fee to the historic church (or equivalent alternative).

Exclusions: Additional food and drink, Souvenirs, Tips/gratuities for your guide

Reviewed By LarryGNewYork

I have been to Boston many times, but this tour was as if I had landed in a completely different city with it’s Italian charm fused together with American history. Our tour guide Bob made the journey especially fun, as well as educational, but he was no match for the mouth-watering food around every corner and alleyway. Here’s to the Red, White and Blue!…as in blew me away. Viva Italia!

8. Boston City view Bicycle Tour

Urban AdvenTours, 103 Atlantic Ave, Boston, MA 02110, USA Urban AdvenTours
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4.8 based on 294 reviews

Discover Boston’s famous sites and hidden treasures on this 2.5 to 3-hour guided bike tour – a perfect way to explore the city! Start at Little Italy in Boston’s North End and pass sites like Copley Square, Fenway Park and the Faneuil Hall marketplace. Cruise through Beacon Hill and admire the diverse neighborhoods as your knowledgeable guide provides insightful commentary on Boston’s unique history. You may also choose to do this tour on an e-bike (select e-bike option at checkout, but note: you must be 16 or older to select the E-bike option).

Inclusions: 2.5-3 Hour Guided Bicycle Tour of Boston, Choice of Hybrid Bike or E-bike , Explore 6 Boston neighborhoods including historic North End "Little Italy" and Back Bay, See top Boston attractions including Fenway Park, Boston Common, and Copley Square, Helmets Provided

Exclusions: Gratuities

Reviewed By 259allenf

I rented a bike for the day. Great bike - helmet, bike pump, flat kit, and lights included. Had a nice conversation about places to bike, and was given a map with several bike trails and places of interest. Friendly, professional, convenient and quick, and the bike was a sweet ride.

9. Sightseeing Day Sail around Boston Harbor

Classic Harbor Line Boston, 60 Rowes Wharf, Boston, MA 02110, USA Classic Harbor Line Boston MA Day Tours
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4.7 based on 22 reviews

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard beautiful schooner Adirondack III, an 80-foot pilot schooner of the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of Boston from the water! Within minutes of leaving the dock, guests will forget the distractions of life on land and experience the joy of a leisurely sail. Sit back and relax as the crew raises sail and provides beverage service. Drinks are available for purchase by credit card only. Guests are welcome to bring a picnic onboard. The knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer.

Inclusions: Duration: Choose between a 1.5 or 2 hour sailing experience

Exclusions: Beverages are not included, but are available for purchase by credit card only., Soda & Water is $2.00, beer is $6.00, wine is $7.00/glass, and mixed drinks are $9.00., Gratuities (recommended for the captain and crew)

Reviewed By LaurMorg

If you have even the slightest amount of covid anxiety this is not for you. Firstly, the staff member who took our tickets when we entered was not wearing a mask and he did not wear one throughout the course of our time on the boat. Furthermore, the tables and chairs on the outside deck were not thoroughly cleaned and were not spaced apart from one another. There was no enforcement of mask wearing when people were out of their seats, and the line for brunch was not socially distanced. The women's bathroom was also filthy, though the men's was not as bad. Also, this is advertised as a Fall foliage cruise yet there is no foliage given that it is on the harbor. You do see a lot of container yards and apartment complexes so if that is your thing then you might like this. I will say that the food was decent and the drinks were very good. Would not recommend, especially not during covid.

10. Boston's North End "Little Italy" Pizza, Cannoli, and History Walking Food Tour

Tony DeMarco Statue, 191 Hanover St, Boston, MA 02113, USA Boston Pizza Tours
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4.7 based on 248 reviews

Treat yourself to some of the best pizza in Boston on this North End History & Pizza Walking Tour through Boston's "Little Italy". See the sights as you walk in the footsteps of Revolutionary Patriots like Paul Revere, Samuel Adams and George Washington. During this fun history walk you’ll see FIVE Freedom Trail sites, plus enjoy THREE different slices from some of Boston’s very best Pizzerias. Pizzerias on tour can rotate from day to day, and may include – a slice named in the “Top 25 Best” in America by a Famous Food Critic, a slice from Boston’s oldest Pizzeria with a brick oven from 1883, a “Secret Underground” spot for grilled flat-bread Pizza, or from a restaurant named one of the “Top 10 Best” Italian Restaurants in the World! Bonus Stop at Modern Pastry to finish with a FREE cannoli! See top Boston sites including Paul Revere House, the Skinny House, Bunker Hill Monument, USS Constitution, and Copp's Hill Cemetery.

Inclusions: 2+ hour History & Pizza Walking Tour of Boston's North End, Visit campus of historic Old North Church & The Clough House, Enjoy 3 Pizza Tastings from some of "Little Italy's" Top Pizzerias , See 5 Freedom Trail Sites along your route, including Paul Revere House, Bunker Hill & Old Ironsides, Walk in the footsteps of Revolutionary Patriots like Paul Revere, Samuel Adams and George Washington, Professional/Local Guide, Bottled water, Cannoli from Modern Pastry

Exclusions: Gratuities

Reviewed By Chisholmfamilytravel

Nicole was a great tour guide. Being in the basement of the Old North Church was adventurous and fascinating! The pizza was great from all 3 pizza spots. A great, interesting tour of the North End. Highly recommend!

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