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Walking tours for the passionate traveler

Want to escape the tour bus crowd and experience Boston through the eyes (and feet) of a local?  Explore some of the city’s charming neighborhoods?  See, taste and smell our food?   Discuss architecture, culture, sport or movies?   Then a private, walking tour by Insider’s Boston is for you. 

What you'll see.

Your tour will be tailored to your interests, based on a brief conversation the night before.  Tours will concentrate on Boston’s downtown, where much of the City’s history and culture is concentrated.  Below are some of the places and things you will see.


There's more to Boston than the Freedom Trail

Join Bill Fleming, an enthusiastic Bostonian, in exploring every aspect of the city as you walk through 5 different neighborhoods.  You will learn about Boston’s past and recent history, our unique culture and attitudes, the food and restaurant scene and more.  Each 3-hour tour is personalized, and with no more than 6 people, there is plenty of opportunity to explore the topics that interest you.  Get an authentic understanding of the city and its people by joining Insider's Boston on this private walking tour of one of America's most historic cities.

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Bill Fleming, your Tour Guide

Bill will share his love for Boston and make you laugh in the process (or at least try).  He:


  • Is a loooong-time Boston resident with a background in city planning

  • Can talk about food and wine for hours and is always trying new restaurants 

  • Follows local issues such as the economy, crime, movies and transportation

  • Loves to discuss Boston sports, including the Patriots.  (But don’t hold that against him.) 

  • Is absurdly interested in Boston history and culture

  • Will spout an interesting fact without warning


You will feel like old friends in 3 short hours. 

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