What to do and see in Boston, Massachusetts (MA): The Best Historical & Heritage Tours

October 8, 2021 Brandee Mangan

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. Private Day Trip From Boston to Salem

Elite Limo Boston
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5.0 based on 4 reviews

Take a break from Boston and head north to explore spooky Salem, Massachusetts! With this private, full-day trip you'll enjoy roundtrip transportation with a private driver who will escort you to and from your hotel or local Boston accommodations. Discover Salem's haunted history, learn about the infamous Witch Trials, and run into a few practicing witches along the way.

Inclusions: Private day trip

Exclusions: Food and drinks, Gratuities

Reviewed By dmsibert08

My goodnes it was all good! Dave was amazing and knew his stuff. The views were awesome! I enjoyed it!

2. Ultimate Boston Self-Guided Combo Tour

Boston Common, 139 Tremont St, Boston, MA 02111, USA Boston City Day Trips
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5.0 based on 1 reviews

Explore Boston, Cambridge, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), Harvard University, the Harborwalk, and a scenic waterfront drive around nearby Cape Ann. This is the ultimate "must-do" package for a trip to Boston and New England. This self-guided tour allows you to explore Boston’s historic wonders with maximum flexibility and value. Purchase one tour per car. Everyone can listen at the same time! Within 30 mins we'll send you a unique password and an app. Download the app onto your phone, enter the password, and download tours. Head over to the first stop. Launch the app and simply follow the instructions from there! Stick to our recommended route and speed limit for the best experience. No expiration — the tour is available from the minute you book until forever! This tour does not include entrance to attractions along the route. Check pandemic rules and opening hours before your visit.

Inclusions: Freedom Trail Tour (Languages: English, Spanish, Chinese), Harborwalk and Tea Party Tour, Scenic Cape Ann Tour, Harvard Yard Tour, Cape Cod and Provincetown Tour, GPS Map, Audios and Text, Online Support

Exclusions: Admission to Paid Attractions

Reviewed By Trek697070

Loved that the tourguide started the topic before we arrived at the destination and was occasionally comical. Didnt love that the map feature didnt let us know when we detoured. Would like to see "places to park" especially if you have an oversized vehicle.

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. Private Boston North End Pizza, Cannoli and History Walking Tour (2 - 4 Guests)

191 Hanover St, Boston, MA 02113, USA Boston Pizza Tours
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5.0 based on 1 reviews

Tour like a Local with a Private Guide! Treat yourself to some of the best pizza in Boston on this Private 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 Burying Ground.

Inclusions: Visit campus of Old North Church / Clough house, Enjoy 3 Pizza Tastings from some of "Little Italy's" Top Pizzerias , Professional/Local Guide, See 5 Freedom Trail Sites along your route, including Paul Revere House & USS Constitution, See top historical sites such as Bunker Hill Monument, Skinny House, and USS Constitution, Bottled water, Finish with a cannoli from Modern Pastry!

Exclusions: Gratuities

Reviewed By bluemoosecda

My wife and I have done numerous food tours across the US and internationally. We love food tours so much that we started one in our hometown. This one proved to be one of the best. Our guide, Martin, had a great sense of humor, lots of interesting stories, not just info. You could tell he loved the food tour, loved Little Italy and loved sharing it with us all. Arrive with an appetite, three full size slices await you. We were so full we waited until later to eat our cannolis. When we return to Boston, we will stay in the area and enjoy those restaurants again.

5. 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.

6. 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.

7. 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!

8. 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!

9. Boston to Plymouth Small Group Day-Trip with Plimoth Plantation & Mayflower II

Boston Marriott Long Wharf, 296 State St, Boston, MA 02109, USA New England Trips
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4.7 based on 37 reviews

Leave Boston behind and visit two iconic Plymouth Attractions. Help celebrate Plymouth's 400th Birthday on this day trip to "America's Hometown" Plymouth, MA. This unique day trip travels through "The City of Presidents" Quincy, MA where you'll visit the birthplaces of two U.S. Presidents, John Adams and John Quincy Adams. You'll also travel along the coast through the beautiful towns of Cohasset, Scituate, Marshfield and Duxbury. While en route to Plymouth you will learn about this historical area of Massachusetts called the South Shore. Upon arrival in Plymouth you will have time for lunch on the Harbor. After lunch the rest of your day will be spent viewing Plymouth Rock, boarding the Mayflower II and visiting Plimoth Plantation. There are also other surprises on this trip that will have you in awe! This magnificent day trip is one that you surely will never forget!

Inclusions: Round-Trip Transportation via air-conditioned Mini Coach Bus, Hotel Pick-Up/Drop-Off included at select Boston hotels, Skip-The-Line Admission to Plimoth Plantation, Complimentary snacks and bottled water, Professional Guide, Admission to the Mayflower II

Exclusions: Gratuities (recommended), Lunch may be purchased at a Plymouth Harbor restaurant of your choice

Reviewed By rjgrjgrjg

Perfect day trip from Boston! Our Boston driver, Kevin, was wonderful and pointed out places of interest as we made our way through and out of Boston. He made sure everyone knew the drop off and pick up times/locations. I opted for the 3 hour island tour and loved it! The guide, Tom, was fantastic and his love for island showed! I would definitely do it again and I live in Boston.

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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