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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
99 Reviews (4.83)

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

ELLEN was fantastic!
Our guide, Ellen, was fabulous! She had so much knowledge about Boston and was ready to adapt our tour for our interests. I would take another tour with her - or with any context guide - any time. I live in Boston and am so glad to have taken the time to learn more about my hometown!
Not up to quality of previous Context tours.