Our Harbor Cruise inclusion ends Nov. 14. Gold & Platinum pass holders will receive an extra day on the trolley starting Nov. 15. Check schedule for details. Read our tour updates & safety information.

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Old Town Trolley Old Town Trolley Tours Boston sightseeing tours
Boston tours
Boston trolley driving past Boston Public Library
About Us

Meet Our Conductors


Our Conductors


Here at Old Town Trolley Tours of Boston, we pride ourselves on having the most highly trained, historically accurate, knowledgeable, entertaining, professional, and safe group of tour conductors ever assembled under one orange and green roof. Who are these fascinating people who become “ambassadors of Boston” for the thousands of guests who visit our beautiful city each year?


There is no designated career path that one takes to becoming an Old Town Trolley Tour conductor. One doesn’t start off as a youth driving a VW Beetle, talking about their neighborhood, then graduate to a mini-van explaining the Revolution to their relatives, until they are finally ready to drive a 36-passenger sightseeing trolley and share the deep history of our 370 year old city. Our Tour Conductors are a diverse and eclectic group, and come to us from a wide range of professional backgrounds. They range from our early 20s aged Rock-a-Billy singer/songwriter to our semi-retired former corporate VP, and everything in between. What they do share is a passion for history, a love of Boston, and the unique ability to tell a story in such a way that people are riveted to their every word. Most conductors seek Old Town Trolley out as an occupation, not the other way around.


We do help them along with our extensive, six-week training program that teaches the conductors to safely navigate a large tour vehicle around the most demanding city, driving-wise, in the U.S. The program includes safety training, interpersonal hospitality skills, performance elements (such as playing sound effects), and of course a wealth of information about Boston’s history, architecture, and lore. We teach the conductors how to keep our guests safe and sound while being a historian, an entertainer, and a city concierge, all rolled into one.

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