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
162 Reviews (4.75)

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 had a fantastic experience with Christian from Context. He is incredibly knowledgeable, personable and wonderful about tailoring our visit to satisfy our child’s curiosity. Highly recommend.
Great dive into the history of Boston with some awesome stops along the way!
Jessica was fabulous and so informative. It was fun walking around the North End and learning about her neighborhood Everyone knew her. She also suggested a great Italian restaurant for lunch!!