BOSTON · MASSACHUSETTS
Boston’s best days out.
The 15 most popular historical tours in Boston. The ones worth building a day around, with prices, run times and who runs them.
A 2.5-hour small-group Freedom Trail walk with a historian guide, covering all 16 sites and the Revolution era 1760–1775.
Most Popular“Meagan was great and very knowledgeable and had a passion for history and a great storyteller! I learned so much!”
Tour Fenway Park with a guide: Green Monster, Pesky’s Pole, Living Museum exhibits, and Red Sox World Series history in 1 hour.
“Great experience. Highly recommended if you come to Boston on vacation. Fun tour guides very friendly and knowledgeable”
Taste North End bread, pizza, and deli sandwiches, then walk the Freedom Trail from Boston Harbor to the Public Garden.
“Ilan was our guide and he was great. I feel like we covered a perfect amount of must-sees for first time Boston visitors. Our time in the North End was fantastic. Unforgettable.”
A narrated cruise from Long Wharf that passes USS Constitution, Bunker Hill, and Old North Church, with harbor stories in 1 hour.
“We had a wonderful time and our caption was funny and easy to listen to during the tour.”
A narrated 1-hour Boston Harbor cruise from Long Wharf, passing USS Constitution, Tea Party ships, and Boston Light, with skyline views.
“Nice one hour boat trip, quite educational about Boston. Indoor area great during winter. Outdoor space open in the winter also. As functional bar for snack snacks, and drinks.”
Boston’s North End Food Tour blends Italian tastings, Old North Church history, and a small-group walk for real neighborhood flavor.
“This tour was off the charts. Definitely the best food walking tour I've been on. Nabil was so knowledgeable, funny, and really present with each of us. He obviously loves what he does. We all felt so special as he guided us straight to hidden gems we NEVER would have found on our own, where…”
Follow the Freedom Trail on a Boston pizza tour through the North End, with 3 full-size slices and a Modern Pastry cannoli finish.
“Pizza tour was great, only problem was that it was so cold out that day. But the tour itself was interesting and the food was good.”
Walk Boston’s donut trail with tastings at classic shops, apple cider stops, and North End history on a guided 2-hour route.
“It was a great experience with Stephanie. You get to walk around with others and learn Boston history along with sampling donuts.”
Small-group Freedom Trail pub crawl with local history at four close-by bars near Faneuil Hall. Pay for drinks as you go.
“Sent a group of customers on this tour and they loved every second of it! Awesome tour guide and great entertainment”
Small-group Freedom Trail walk from Boston Common to the North End, covering all 16 sites with lively Revolutionary stories for $39.
“Our guide Nick was fantastic. He was informative, interesting, and a wonderful tour guide. He kept the tour on track and was great at answering questions. I’d take another tour with Nick any time!”
Ride Boston’s top sights by bike for about 2.5 hours. Freedom Trail crossings, Fenway, Back Bay, North End, and great guides for $78.
“A comprehensive cycle tour of Boston Central and its suburbs. Easy cycling with lots to see and knowledgeable guides.”
Boston History Tour, $39.80: a 2-hour small-group walk through Faneuil Hall, Beacon Hill, Old State House and Public Garden.
“You get to see a lot of different parts of the historical areas of Boston. There was so much information given along the tour. Our guide was great!”
A small-group North End walk with history and serious Italian tastings, including lunch with wine pairing and desserts like cannoli.
“This is a very informative and engaging tour both about the food and the history of Boston’s north end.”
A 90-minute Freedom Trail walk in Boston with a costumed guide, included admission stops, and a good pace for time-pressed visitors.
“It was super informative and engaging. The tour guide had so much knowledge he guided you into the experience as if it was the 1700.”
A 2-hour Freedom Trail pub crawl with a local guide, 4 bar stops, and history stories tied to Boston beer and revolution.
“Anna was wonderful and so accomodating! Beers were fantastic!”
Every neighbourhood in the city, and every road out into New England.
