Boston private tours and Boston small group tours

Boston Tours and Experiences Hosted by Local Experts

Dig deeper into American history alongside a local expert with our captivating walking tours and illuminating pre-trip online lectures. Context experiences are all hosted by our world-renowned experts — from historians to art curators and other specialized experts. 

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
157 Reviews (4.75)

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Jim did an excellent tour which he modified given the rainy weather conditions. It was fascinating and he was very knowledgeable about the history of the area, architecture, and development of the region. He was very flexible and willing to follow out interests for the tour. I would highly recommend him.
Jessica was great. Very knowledgeable and kept a good pace to our tour. Took us to notable and important sites and explained well the history and importance of each spot.
Ellen was a terrific guide. She managed to tell a great story of Boston with sequence and detail that kept us, and our 11 year-old, engaged throughout.