Boston Private and Small Group Walking Tours
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. Join us on our Context Boston private tours and Boston small group tours.
Boston Private Tours and Boston Small Group Tours
What makes our Boston private tours and our Boston small group tours in Boston different is that they’re extremely small—6 people max—and led by credentialed Boston private guides, PhD or MA-level in their respective field. 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
124 Reviews
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Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.
We always love Context but today was a low point. Our guide was lovely and obviously intelligent and well informed but her style was disorganized and rambling and we never got a real picture of the history of Boston. We spent time hearing about her family history and we were, honestly, not interested. My daughter is usually easily engaged but she was bored because the narrative was really hard to follow.
Allison
Feb. 18, 2023
Ellen was fantastic, please schedule warmer weather next time :)
Tim
Dec. 12, 2022
Jessica is amazing! Her wealth of knowledge is truly astonishing. Her ability to clearly share information was appreciated by this nonprofessional audience. We never once felt that there would be a pop quiz…although we would have been prepared by Jessica! AND, we now know T.H.E. best spots jn the area to get amazing Italian food. YUM! Yes, a truly comprehensive tour, chock full of important and interesting information :)). Can’t recommend Jessica highly enough. Don’t miss her tour!
Lloyd
Nov. 12, 2022