Are you looking to explore Boston like never before? Are you tired of the same old, monotonous guided tours that make the American Revolution sound like a snooze fest? Welcome to the Improv Asylum’s Comedy Trolley Tour of Boston, where history lessons meet belly laughs!
Every Saturday, we take the spirit of our comedy club on the road, or more precisely, on the rails, as we guide you through the rich tapestry of Boston’s history, culture, and, yes, quirks. But forget the yawns and stifled giggles you’ve experienced on other city tours. Our Comedy Trolley is designed to keep you engaged, entertained, and—most importantly—laughing your socks off!
Your Saturday Just Got Funnier
What better way to spend a Saturday than jumping onto a trolley designed for maximum hilarity? The tour begins at Improv Asylum, located in the heart of Boston’s historic North End. Once everyone is on board and settled, our stand-up comedians—disguised as tour guides—take center stage. These comedic maestros double as historians, weaving well-researched facts with humorous takes on Boston’s past and present.
Not Just a Laugh, It’s an Education
Did you know that the Boston Tea Party wasn’t a party but a political protest? Or that Paul Revere never shouted, “The British are coming!” but likely warned more covertly? Prepare for an irreverent deep dive into the events and personalities that shaped this fantastic city. Our comedians deliver your history lesson with impeccable comedic timing, turning even the dullest fact into a punchline.
The Stops Along the Way
Our Comedy Trolley doesn’t just ride through history; it makes pit stops at iconic landmarks like Fenway Park, Quincy Market, and the Freedom Trail. At each location, the comedy keeps rolling. Imagine trying to keep a straight face as your guide offers a satirical narration of Samuel Adams as a Founding Father and a “revolutionary brewmaster.” Or picture the hysterics when you learn about the “real” witches of Salem. Yes, there’s a photo-op at every stop, but we guarantee that your pictures will capture more than smiles—they’ll capture full-blown laughter.
All Are Welcome
Bostonians, students, tourists—our Comedy Trolley Tour is for everyone with a funny bone. It’s family-friendly, so bring the kids or make it a unique date night. You might find our version of Boston’s history more memorable (and more Instagrammable) than anything you’ve ever experienced.
Book Your Spot Today
Seats on our Comedy Trolley Tour sell out quicker than you can say “Lobstah!” Given that it only runs on Saturdays, we recommend booking in advance to reserve your spot for Boston’s funniest tour.
So, what are you waiting for? All aboard the Laughter Express! Your journey through the Cradle of Liberty will never be the same again. Because at Improv Asylum, we believe that history doesn’t have to be boring—and we have a Comedy Trolley to prove it.
To reserve your seat or learn more, click here. Laugh and learn with us as we take you on an uproarious journey through Beantown. We guarantee that you’ll disembark with a deeper appreciation for Boston and sore cheeks from smiling so much. See you on the trolley!





