Where to Start: the 10 Best Boston History Tours

1.Boston: Freedom Trail History Small Group Walking Tour

★★★★★★★★★★5.0 · 6,450 reviews · 2 hours 30 minutes (approx.) · from $35Our pick

Follow Boston’s full Freedom Trail from Boston Common to Copp’s Hill Terrace with a historian guide. Expect a 2.5-hour walk through Revolutionary sites, lively storytelling, and time for questions. Guides such as Jon, Maura, Mark, and Alejandro are praised for making the past clear and memorable.

“Fantastic tour guide and a great walking tour of the city. Great history and city tour. I would highly recommend.”

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2.Tour of Historic Fenway Park, America’s Most Beloved Ballpark

★★★★★★★★★★4.5 · 3,013 reviews · 1 hour (approx.) · from $45

Spend about an hour inside Fenway Park with a professional guide, visiting the Green Monster, Pesky’s Pole, roof deck, and Living Museum. Guides such as Steve, Matt, Jack, and Mary Ella have led lively tours, while bilingual Spanish and Japanese tours can be arranged in advance.

“Getting to visit almost all parts of this historic ballpark was a last-minute decision that we are very glad we made! Even on a chilly evening, hearing the stories and facts was informative and memorable. We were outside more than I thought we’d be, so definitely dress for the weather, but also definitely make it a stop!”

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3.Boston Food & History: Pizza, North End & Freedom Trail

★★★★★★★★★★5.0 · 1,772 reviews · 5 hours (approx.) · from $90

Spend about five hours walking from Boston Harbor through the North End and along the Freedom Trail. You’ll taste bread, pizza, an Italian deli sandwich, coffee, and pastry, then finish near the Public Garden after stops at Old North Church, Granary Burying Ground, Beacon Hill, and the State House.

“Great way to see the city and enjoy local foods. Our tour guide Elon was exceptional. Very knowledgeable and engaging”

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4.Boston: Freedom Trail History Small Group Walking Tour

★★★★★★★★★★4.9 · 1,590 reviews · 2h 30m · from $35

Follow Boston’s 2-mile Freedom Trail with an English-speaking guide and no more than 15 people. You’ll see 16 official landmarks, from Granary Burying Ground to Old North Church, then finish near North End restaurants with views toward the USS Constitution and Bunker Hill.

“I think a way to keep track of the freedom trail things we've seen as we go by would've been good. think like a hit list. there's just so much going on it's easy to get lost in the sauce”

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5.City Cruises Boston Historic Sightseeing Harbor Cruise

★★★★★★★★★★4.5 · 1,388 reviews · 1 hour (approx.) · from $46

Cruise Boston Harbor for 60 minutes with live narration about the Revolutionary War, Boston’s working waterfront, and figures such as Paul Revere. You’ll pass USS Constitution, Boston Light, Fort Independence, and the Boston Tea Party ships. Guides including Kevin, Holly, Mike, and Jeff have earned special praise.

“Very informative and great way to spend a rainy day in Boston. Would definitely recommend to anyone!”

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6.Boston Pizza Lovers Food and History Walking Food Tour

★★★★★★★★★★4.5 · 1,082 reviews · 2 hours 50 minutes (approx.) · from $69

Walk Boston’s North End with a local guide such as Scotty or Big Al, tasting three full-size pizza slices along the way. You’ll see Paul Revere House, Old North Church, Copp’s Hill, Old Ironsides, and Bunker Hill, then finish with a Modern Pastry cannoli.

“Scotty was a great guide. Very knowledgeable about the entire area. It was a fun twist on a history tour to get pizza along the way.”

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7.Boston Freedom Trail History Pub Crawl Small-Group Tour

★★★★★★★★★★5.0 · 996 reviews · 2 hours 15 minutes (approx.) · from $60

Meet your guide at the Samuel Adams statue beside Faneuil Hall for a 2-hour-15-minute tour through Boston history and local pubs. Guides such as Maddie, Julie, Sam, and Anna mix revolutionary stories with drink advice. Expect four nearby bars, only two blocks of walking, and drinks purchased separately.

“A really fun way to learn key historical facts and see a bit more of Boston- while the actual walking portion of the tour is very short I still left feeling like I had seen things I would not have visited otherwise, and having learnt a lot (as a visitor from the UK where the revolution etc isn’t something we learn about in school!). Our guide was very fun as well as knowledgable, and made the experience what it was. As a solo traveller, it was great to meet more people and about half our group ended up continuing the night for more drinks after the tour ended.”

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8.Boston City View Bicycle Tour: History and Landmarks

★★★★★★★★★★5.0 · 638 reviews · 2 hours 30 minutes (approx.) · from $78

Ride about 8 to 11 miles through Boston with guides such as Gary, Costa, Austin, and Charles. You’ll pedal past Fenway Park, Beacon Hill, Copley Square, the North End, and the Freedom Trail, with regular stops, city bikes or optional pedal-assist e-bikes, and helmets provided.

“Great way to see and get oriented to the city for first timers. Bikes are in very good condition and the guides shared useful information.”

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9.Boston History Tour: Scenic Walk Through Time & Landmarks

★★★★★★★★★★5.0 · 627 reviews · 2 hours (approx.) · from $39

Walk about 4 km through Boston with guides such as Bob, Nabil, Lexie, or Allison. Visit Faneuil Hall, the Old State House, Boston Common, Beacon Hill, and the Public Garden while hearing local stories and getting practical tips.

“This was such a great way to explore and learn more about Boston. I feel like I definitely got a great overview of the city’s history. And Nabil was such a great tour guide! Our group had lots of questions and he happily answered all of them. He was patient, flexible, and made all feel welcome. I’d recommend anyone visiting Boston for the first time to take the tour!”

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10.Boston’s North End Food and History Walking Tour

★★★★★★★★★★5.0 · 459 reviews · 3 hours (approx.)

Walk Boston’s North End with local guide Paula, tasting arancini, Sicilian pizza, olive oil, cheese, pasta, cannoli, gelato, and espresso. The three-hour route visits family-run shops, an Italian market, bakery, café, and restaurant, with a two-course lunch and wine pairing.

“Paula is welcoming and full of interesting history of Little Italy. We enjoyed every stop! You are definitely getting a locals perspective of delicious bites and sips. Cannot pick a favorite each stop was so good! As an extra, learned so much about the history of this little neighborhood. ❤️”

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