The 10 Best Sightseeing Tours in Boston, Massachusetts (MA)

November 27, 2021 Flossie Demartino

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. Boston's Beacon Hill Guided Photography Walking (Small Group)

34 Beacon St, Boston, MA 02108, USA PhotoWalks Tours of Boston
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5.0 based on 22 reviews

Walking along the picturesque streets of Beacon Hill is an immersion into a 19th-century English-inspired neighborhood that's rich in history and charm.  Learn how to compose amazing pictures of Beacon Hill’s diverse architecture, antique gas lamps lining the brick sidewalks, colorful flowers spilling out of the window boxes, the most photographed street in Boston as well as an exclusive enclave and other surprises hidden in unexpected places.  Fascinating commentary on Beacon Hill's historical sites along the itinerary is also provided throughout the tour.

Inclusions: Professional Tour Guide, Small Group Tour, Fascinating historical commentary, Creative photography tips to capture amazing pictures with your camera or smartphone

Exclusions: Gratuities

Reviewed By 388adamd

My students and I enjoyed a phenomenal Freedom Trail tour with Saba. She was patient, informative and engaging. My third and fifth graders came out of the experience with big smiles, great photos, and a stronger understanding of the role of Bostonians, and Boston itself, in the Revolution. I would recommend this tour and any other that Saba offers.

3. 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.

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. 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 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.

8. Sip of Boston Guided Brewery Tour

2 Park Plaza, Boston, MA 02116, USA City Brew Tours
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4.8 based on 106 reviews

The Sip of Boston Tour is the perfect introduction to Boston's impressive and world-renowned craft beverage scene. On this compact, three and a half hour adventure, you will go behind-the-scenes of three of Boston's local craft alcohol producers while enjoying tasty pretzel and cheese snack to soak up all those delicious suds.  

Inclusions: Tastings, as noted, Bottled water, Craft beer Pretzel Snack, Guide, Transportation, For bookings of 4 or more guests a gratuity is included in your ticket price. No need to tip.

Exclusions: Hotel pickup and drop-off, Guests under 21 years of age

Reviewed By Staravalos81

If I could this company a negative I WOULD! Stay away from this company. By far the worst customer service ever. I am an event planner who gave them a lot of business and not one tasting went smoothly. Missed packages, beer kits never had all the correct items one paid for. No tracking is given to track the kits sent to your group. The host has no idea what's even in the kit and tasting he/she is doing. Just stay away and give your business to a company that actually cares instead of this joke of a company!

9. Boston Harbor Sunset Cruise

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 43 reviews

Enjoy a relaxing sunset cruise in Boston Harbor which heads out to Fort Independence located on Castle Island and named after George Washington. Then take in views along Boston's waterfront such as the Mystic Tobin Bridge, Leonard Zakim Bridge, Custom House Tower, Old North church steeple, USS Cassin Young, and the USS Constitution.  An extra special feature on this cruise is the cannon fire at Sunset, which is presented off the USS Constitution every night to announce the setting of the sun. Plan to arrive 15 minutes prior to the scheduled meeting time to check-in at the ticket booth, obtain boarding passes and pre-board.

Inclusions: Cruise

Exclusions: Food and drinks (available for purchase by credit card only), Gratuities

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 Duck Boat Sightseeing City Tour with Cruise Along Charles River

Museum of Science, 1 Museum Of Science Driveway, Boston, MA 02114, USA Boston Duck Tours
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4.6 based on 6,210 reviews

Water is no barrier for a duck, why should it be for you? A Boston Duck Tour is a wonderful way to get a great look at Boston on land and water. See all the major landmarks and hear the history of the city as you tour Boston in a renovated World War II amphibious vehicle.

Inclusions: 80-minute Duck Boat Tour of Boston, Narrated tour of Boston with your own personal ConDUCKtor, 20-minute boat ride along the Charles River, Multi-lingual Audio Guides available in English, Spanish, French, Italian, Portuguese, German, Japanese, and Chinese from the Prudential Center and Museum of Science departure locations., See top Boston areas such as Fenway Park, Faneuil Hall, Copley Plaza, and more!

Exclusions: Gratuities, Hotel Pick-Up/Drop-Off

Reviewed By donna-kennyw

Had such a great time learning about Boston from Captain Crazy Beard! He totally was engaged the whole trip and answered any questions we had. Best of both land and sea tour all in one.Would recommend a must see.

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