Top Boston Trolley Tours

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

Experience Boston’s history on a non-stop trolley tour that traces the city’s role in the American Revolution and early United States history. This guided overview provides context on key events, ideas, and figures that shaped the nation, while helping you understand how Boston’s neighborhoods and landmarks fit together. The format offers a time-efficient city introduction without the physical demands of a long walking tour.

70-Minutes NON-STOP Trolley of Historic Boston and Freedom Trail

1 hour 10 minutesFree Cancellation

Explore the best of Boston on this hop-on hop-off trolley tour. Board at one of the stops, then hop off wherever you like, explore independently, and get back onto the trolley when you’re ready. Alternatively, ride the 2-hour loop in one go, listening to the informative commentary. Tickets are valid for one or two days, and while admission tickets aren’t included, enjoy discounts to some top Boston attractions.

Historic Boston HOP-ON/HOP-OFF Narrated Trolley Tour

1 hour 15 minutesFree Cancellation

Boston Ghosts and Gravestones Trolley Tour

Boston Shore Excursion: Boston Hop-On Hop-Off Trolley Tour

Lexington, Massachusetts - Liberty Ride Trolley Tour

Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston. This tour's shorter distance lets you follow in the footsteps of the founding fathers and American revolutionaries without making the more strenuous trek all the way across the Charles River, finishing in a spot that’s convenient to top Boston attractions.

Boston Freedom Trail Walking Tour with Costumed Guide

1 hour 45 minutesFree Cancellation

Likely to Sell Out

City Cruises Boston Whale Watching Cruise by High-Speed Boat

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

4.5

(3,422)

from $86

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

City Cruises Boston Historic Sightseeing Harbor Cruise

City Cruises Boston Historic Sightseeing Harbor Cruise

1 hourFree Cancellation

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

Boston to Martha's Vineyard Day Trip with Optional Island Tour

12 hoursFree Cancellation

Sample some of the tastiest bites that Boston’s North End has to offer—and enjoy a first-hand introduction to the area’s Italian heritage. Choose between our 3-hour or dynamic 2-hour express tour, and bring your appetite: Follow your guide to top-rated local businesses, and try everything from clam chowder and lobster rolls to cannoli. At the end, enjoy a secret dish revealed only on the day of the tour.

Boston North End Food Tour with Authentic Local Flavors & Dishes

2 to 3 hoursFree Cancellation

Price varies by group size

The Full Revolutionary Story Epic Small-Group Boston Walking Tour

3 hoursFree Cancellation

Boston: Freedom Trail History Small Group Walking Tour

2 hours 30 minutesFree Cancellation

Walk the Historic Freedom Trail with Costumed Guide

1 hour 30 minutesFree Cancellation

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

2 to 3 hoursFree Cancellation

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.

Boston’s North End Food Tour: Italian Flavors and Heritage Walk

Price varies by group size

Boston's 250th Freedom Trail Tour

1 hour 45 minutesFree Cancellation

For anyone thinking of attending Harvard, or for those who simply want a glimpse of college life at the famous university, this tour is a must. Get an exclusive account from current Harvard students, who provide key insights into the life and times at Cambridge with a theatrical, humorous flair. Check out the old buildings at Harvard Yard and Harvard Square and learn about the school’s storied past. Illustrated map of Harvard Square included. Choose from several departure times throughout the day.

Harvard University Campus Guided Walking Tour

1 hour 10 minutesFree Cancellation

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

Boston Pizza Lovers Food and History Walking Tour

2 hours 30 minutesFree Cancellation

Must-Dos in Boston

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What are people saying about Boston

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Erin_G, Oct 2026

Fun guide

We had a good experience with another Viator self-guided tour so decided to try this one. This also did not disappoint. The narrator is triggered by your location (gps?) and the narrator offers stories along the way. The trail is so long we only got a quarter of the way through. Not sure if we could have advanced the tape to start on other parts of the trail. I guess we could have since its triggered by our location.

Boston Tea Party Ships and Museum Admission

Pamela_M, Oct 2026

An entertaining history lesson

A great experience for the whole family. The staff keep you engaged. My daughter said "...if history in school was taught this way...I'd remember more..." It was entertaining, a wonderful history lesson, and had us talking about it well after it was over. Highly recommend this experience.

The Full Revolutionary Story Epic Small-Group Boston Walking Tour

Todd_M, Oct 2026

Excellent tour!

Highly highly recommend this tour. Our guide was Tyler. When he introduced himself and said he had a masters degree in American History and used to be a history teacher I knew the tour would be great. Tyler did an excellent job of explaining the sites in a story format. You will not be disappointed in this tour!

City Cruises Boston Whale Watching Cruise by High-Speed Boat

Kathy_K, Oct 2026

Exhilarating adventure!

The boat was comfortable, the crew was great, and the sightings were incredible! Knowledgeable, informative, and conscientious staff. We spotted about 20 whales. 2 were calves that kept playing! It was a wonderful high speed ride out with fantastic views on the way out and back. Highly recommended this trip!

Boston Ghosts and Gravestones Trolley Tour

Anne_F, Oct 2026

Good Time with Ghosts and Graveyards

This is a great tour with fun actors. The trolly is open air, but has roll down windows in case cold or rainy. There is quite a bit of walking and some of the older folks on the tour struggled a bit, so keep that in mind if you have mobility issues. We loved the guide who escorted us on the trolly and the one that took us through one of the cemeteries. Great stories.

Boston North End Food Tour with Authentic Local Flavors & Dishes

Jan_S, Oct 2026

Elizabeth was a fantastic...

Elizabeth was a fantastic guide for our family of 4. She made the food and history approachable for all ages. The kids loved meeting Chef Bob and holding the lobsters. We all had different favorite stall at Boston Public Market and the pizza and cannoli in the north end were all around hits. Elizabeth was great at knowing when the kids were ready to head to the next stop and when they needed a walking break. She also found scenic spots for us to enjoy our bites.

Boston to Martha's Vineyard Day Trip with Optional Island Tour

paul_s, Sep 2026

Martha's Vineyard Bus Tour - September

Driver Jonny Boston did a very good job at providing historic information along the journey both to and fro. He was entertaining and was very accommodating. Only recommendation - is to let some air out of the tires on the tour bus - very hard ride over the pot holes. Anthony, (bus driver on Marthas Vineyard) was very good, as well. He covered a lot of ground, and was both informative & entertaining.

Harvard University Campus Guided Walking Tour

SusanL_R, Sep 2026

Such a fun walk through education

This was such a fun tour! As advertised, these tours are led by students and each adds their own unique flavor. Ours shared school customs, common mythologies, as well as debunking some urban legends. He was so gracious about guiding people to other places they wanted to go, including recommendations of where to eat. We walked away with much more knowledge than when we began.

Walk the Historic Freedom Trail with Costumed Guide

Aisha_A, Sep 2026

Great tour during a layover in Boston.

I had a six hour layover in Boston and decided to take this walking tour to get a quick overview of the landmarks and history. So glad I did! Very informative and easy way to get the lay of the land, learn about the historical sites and their significance. Getting to the tour was really easy using the free silver line bus from the airport to South Station. I didn’t realize it at the time, that I could have taken the red line train to downtown. Instead, I walked the 10-15 minutes—but didn’t mind since the weather was nice and I was able to see other parts of the city.

Lexington, Massachusetts - Liberty Ride Trolley Tour

Rebecca_F, Aug 2026

Hidden History Treasure

Excellent tour guide - learned so much! Trolley car ride was good, but went by so many places so fast it was hard to get any pictures. (but that’s not what the tour was mainly about.) wish the air-conditioning was a little bit stronger, but does not diminish the experience. Thanks, daddy daddy I’ll go get. I’m sorry.

Historic Boston HOP-ON/HOP-OFF Narrated Trolley Tour

Virginia_L, Aug 2026

City View Trolley was well worth our time

Love that i can scan QR code to see where the trolleys are located. The vehicle is comfortable and frequency of pickup was great, didn’t wait long at all for next trolley. Hugo was very a very entertaining guide and Jack from Dorcester was excellent as well with all of his facts and trivia. Thanks to both these great guides