The 15 Best Historic Tours in Boston

Boston: Freedom Trail History Small Group Walking Tour - Starting at Boston Common and the Foundation Monument

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

Walk Boston’s full Freedom Trail with a historian guide, from Boston Common to Copp’s Hill, in a small group of no more than 16.

“Our tour was supposed to start at 11:00 am but was delayed. Apparently the original tour guide didn’t make it to work that day. However, it was worth the delay because the replacement guide was the bomb! She knew sooo much history and details, our 2.5 hour tour was over before we knew it. Such a great experience and definitely a recommended tour.”

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

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

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

Tour Fenway Park in Boston, sit atop the Green Monster, explore Red Sox memorabilia, and hear more than a century of baseball stories.

“This tour was very informative on the history of Fenway park and baseball. Lots of stairs but worth it!”

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

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

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

Taste North End bread, pizza, and Italian deli fare, then walk Boston's Freedom Trail and Beacon Hill on this five-hour tour.

“Best tour loves every minute of it. This is the second time taking this tour. Our host was different and he took us to a few different spots than the first time which was wonderful He was so funny, knowledgeable we were all able to hear him and all questions were answered. Loved it and will come back if I find myself in Boston again Thank you”

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Boston: City Cruises Historical Sightseeing Cruise

4.City Cruises Historical Sightseeing Cruise

★★★★★★★★★★4.6 · 1,771 reviews · 1 hour · from $46

Cruise Boston Harbor for one hour of history, skyline views, USS Constitution, Castle Island, and lively narration from Long Wharf.

“Mike dealt with the disruption by other passengers perfectly. His awareness of the problem with people talking loudly as he was trying to give his tour and his ability to deal with it was very professional and polite. He was very informative and easy to converse with”

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Boston: Freedom Trail History Small Group Walking Tour

5.Freedom Trail History Small Group Walking Tour

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

Follow Boston’s Freedom Trail with a small group, sharp storytelling, famous burial grounds, and views toward the USS Constitution and Bunker Hill.

“Guide was amazing kile It was really interesting and informative”

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City Cruises Boston Historic Sightseeing Harbor Cruise

6.City Cruises Boston Historic Sightseeing Harbor Cruise

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

Review of Boston’s 60-minute historic harbor cruise, with USS Constitution, Boston Light, skyline views, narration, tips, and value advice.

“The tour was interesting and comfortable. It was nice to see Boston from the harbor and the USS Constitution from a closer vantage point. The tour guide gave great information. The only down side was that the sound system was not that clear. With all the noise in the harbor, it was frequently difficult to hear the guide.”

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

7.Boston’s North End Food Tour: Italian Flavors & Heritage Walk

★★★★★★★★★★5.0 · 1,322 reviews · 2 hours (approx.) · from $70

Taste Boston’s North End through bread, salumi, pizza, pastry, coffee, and Old North Church history on a small-group walk.

“Our tour guide was very knowledgeable on the content on the area. Took us to great food spots to sample delicious options. We had a great time. We even got great spots to sample afterwards.”

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Boston Pizza Lovers Food and History Walking Food Tour

8.Boston Pizza Lovers Food and History Walking Food Tour

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

Taste three Boston pizza slices, cannoli, and North End history on a small-group Freedom Trail walking tour.

“Our tour guide was friendly and informative. Pizza at three different stops. All delicious. By the time our cannoli arrived we were full. We will enjoy them soon.”

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Delicious Donuts of Boston: A Sweet History Walking Tour

9.Delicious Donuts of Boston: A Sweet History Walking Tour

★★★★★★★★★★5.0 · 1,038 reviews · 2 hours (approx.) · from $70

Taste Boston’s best donuts while walking from Kane’s to the North End, with cider, local history, and samples at four beloved shops.

“Very nice tour with Katie. Good variety of donuts. I liked that you only got a quarter of each donut so that you didn’t fill up too fast, but then I think it was a little pricey for what you received. Interesting background stories on a variety of topics.”

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Boston Freedom Trail History Pub Crawl Small-Group Tour

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

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

Pair Boston’s Revolution-era stories with four nearby pubs on a lively, low-walking Freedom Trail crawl led by a local guide.

“The description of the tour was, “The Freedom Trail with stops of a couple of historic pubs along the way.” You don’t see the historic part of the pub because we were led into a separate room with no character. The Freedom Trail is completely absent from the tour. The pubs were all next to one another. I really disappointed my family. Fortunately, we have time to walk the Freedom Trail ourselves today. The tour guide could not have peppered her talks with more expletives and meaningless antidotes about our history if she tried. I still gave her a good tip. Perhaps she was not trained, so she could write…”

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Boston City View Bicycle Tour: History and Landmarks

11.Boston City View Bicycle Tour: History and Landmarks

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

See Boston by bike on a 2.5-hour guided ride through six neighborhoods, from the North End and Fenway Park to Copley Square and the Freedom Trail.

“Great balance of riding and stopping to see sights. Guides were friendly, knowledgeable and managed the group well. Highly recommended.”

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Boston History Tour: Scenic Walk Through Time & Landmarks

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

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

Walk Boston from the Greenway to the Public Garden, tracing Revolutionary landmarks, famous graves, grand streets, and local life in two hours.

“This tour was great and a major reason why was our tour guide Conner Bourgoin. He was genuinely excited about giving us all the history details and answering our questions.”

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Boston’s North End Food and History Walking Tour

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

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

Taste regional Italian food, wine, and North End stories on a three-hour small-group walk led by local guide Paula.

“Paula was an engaging storyteller. We got a real sense of the history and culture of the neighborhood and the food was amazing! Every stop was enjoyable. Highly recommend!”

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