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Private and Small Group Guided Tours

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A maze of winding colonial streets, Boston is a backdrop to some of the most significant moments in American history, from revolution to immigration.
One of the busiest shipping ports on the Atlantic seaboard in the 18th century, Boston originally functioned as America’s gateway to Europe. From public spaces bearing the names of America’s founders to former shipping storefronts and longshoreman pubs, this New England metropolis bears the visible markings of America’s birth and evolution to present day. Experience Boston's vibrant past with Context's private and small group guided tours.

Want more than a tour in Boston? Talk to our expert planners about custom and multi-day options at +1 (800) 691-8328. 

Boston Private and Guided Tours

What makes our private and small group guided tours in Boston different is that they’re extremely small—6 people max—and led by credentialed experts. Our favorites? Well, it’s hard to choose, but we really love our Boston’s Big Dig Tour, which looks at the monumental effort to bury a highway beneath the city, one of the most expensive and ambitious public works project in history. We also love our Beacon Hill Tour, which explores the history of Boston Brahmins.
What Context Boston Travelers Say
93 Reviews (4.85)

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Jessica was a delight. We appreciate your running the tour for just the two of us. We learned a lot even though we were in our own backyard
Communication and reminders before the tour were exceptional. Thank you. Having a representative like Christian is a huge plus as he is exceptional. Knows his stuff and is a great story teller. One of the best tours I have ever taken.
Christian was knowledgeable and included stories to illustrate history. He was responsive and made a great recommendation for lunch - Lemoncello. It was a great 3 hours.