USA · HISTORICAL TOURS IN BOSTON
Every trip has one free day too few. These 13 historical tours in Boston justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Walk Boston’s full Freedom Trail with a historian, from Boston Common to Paul Revere’s North End, with stories, sights, and practical tips.
“Nick was well-spoken and obviously loves the history of his community. Appreciated the tour as my 20 year old son and I enjoyed the city!”
Tour Fenway Park with a guide, sit atop the Green Monster, see rare Red Sox memorabilia, and hear 100 years of Boston baseball stories.
“Our tour guide Matt was very informative and funny. It was really cool to be able to watch the sun set from the press box and see all the exclusive Red Sox memorabilia. Great date night.”
Taste North End bread, pizza, and Italian specialties, then follow Boston’s Freedom Trail from the harbor to Beacon Hill.
“We had a great time sampling Boston's food and learning about the history. Our guide Lexie was great and had as a local had insight others may not have.”
Cruise Boston Harbor for one hour of history, skyline views, USS Constitution, Castle Island, and lively narration from Long Wharf.
“Super fun cruise around the Boston Harbor with Holly. We really enjoyed seeing the city from the water and learning about the history of the Harbor. Holly was fantastic! We got to watch the planes flying right over us as they landed at Boston Logan. Amazing!”
Review of Boston’s 2.5-hour small-group Freedom Trail tour, with 16 landmarks, strong storytelling, cemetery stops, and North End views.
“Toby did a great job of explaining the history in an entertaining way—I definitely left retaining knowledge instead of being overwhelmed and not retaining anything. It was nice that half way through the walk you get a brief stop to use the bathroom and grab a drink if needed. Definitely worth the money!!”
Cruise Boston Harbor for Revolutionary War stories, USS Constitution views, Boston Light, skyline panoramas, and a practical one-hour introduction.
“It was ok. The windows on the lower deck were dirty and difficult to see out of. There were not many snacks to choose from even though it looked as if they had had quite an assortment before. It was difficult to hear/understand the tour guide on the lower level. But it was only $45 so it was not terrible”
Taste Boston’s North End through bakeries, salumeria, pizza, espresso, and Old North Church on a small-group food and history walk.
“We had a wonderful experience! Our tour guide , Lexie, was great. The food was delicious. Loved going into the Old North Church. Loved the history!”
Eat three Boston pizza slices, tour North End Freedom Trail sites, and finish with a Modern Pastry cannoli on this 2.5-hour walk.
“Big Al was the best guide - full of fun energy and enthusiasm for Boston’s History! The pizza places he took us to were all delicious and the cannoli at the end was wonderful! Gave us lots of other recommendations for restaurants nearby.”
Taste Boston’s best artisanal donuts while walking from Kane’s to the North End, with cider, local history, and guides such as Jackie and Lucy.
“This is an amazing experience! You try donuts from a few places and everything was delicious! It’s a great way to see Boston, eat fantastic donuts and get to meet other donut lovers!”
Walk Boston’s Freedom Trail with a local guide, hear colonial stories, and visit four nearby pubs on this relaxed small-group crawl.
“Nicole was great! Very energetic and personal with all participants! Great time meeting other people!”
See Boston by bike in 2.5 hours, from Fenway Park and the North End to Copley Square, the Esplanade, and the Freedom Trail.
“Loved this ride. It’s supervised by three very friendly retired guys. They keep you safe when cycling and provide interesting background and history about Boston at frequent stopping points. The bikes are very good quality. This is a great way to see the city.”
Review of Boston’s two-hour history walk, covering Faneuil Hall, Beacon Hill, Boston Common, burial grounds, local treats, and practical tips.
“Allison was terrific and so much fun. She was knowledgeable and has a funny sense of humor. We were able to see so much of the city and historical sites. It is 2 hours but didn’t feel long. We had a great time!”
Taste Boston’s North End through family-run shops, Italian specialties, wine, and local history on a three-hour small-group walk.
“Excellent experience! The history lesson well appreciated received on the neighborhood and Italian culture overall was really cool. The food was fantastic! We did not leave with empty stomachs. Stopped at places I would have never of seen or thought of going into. Our tour guide Paula is fabulous. She is a walking history book. 10/10 would recommend this to anyone!”
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