Boston Private and Small Group Guided 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.
Looking for something special?
Boston custom tours and trip planning
starting at $1,100.
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
101 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.
Christian was extremely knowledgeable and interesting. We loved our tour and highly recommend it. Best way to see Boston.
Anne
Jun. 13, 2021
ELLEN was fantastic!
Amie
Feb. 18, 2020
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!
April
Dec. 27, 2019