The Massholes Comedy Trolley Tour of Boston

Join the Massholes Comedy Trolley Tour for laughs, free beer, pizza, and Boston’s best sights with hilarious local guides.

Duration: 2 hours
Cancellation: 1 day learn more
Highlights
  • Old State House - The site of the Boston Massacre!
  • Granary Burying Ground - The final resting place for patriots like Paul Revere, Sam Adams, John Hancock, and many more!
  • Back Bay - Boston’s swankiest address, since the 1880’s!
  • Theater District - Boston’s home for world-class entertainment, from standup to Broadway!
  • Chinatown - Boston’s most vibrant neighborhood, and the largest Chinatown in New England!
  • Waterfront - The Big Dig has come and gone, and Boston’s Waterfront looks better than ever! Stroll along the 1.5 acre Rose Kennedy Greenway!
  • North End - Old World charm and the best food in the city, all within a third of a square mile!
  • Charlestown Navy Yard - One of Boston’s oldest neighborhoods, Charlestown is steeped in history. It’s the home of the oldest warship on earth - the USS Consitution - and the site of the Battle of Bunker Hill!
What's Included
  • Snacks
  • Complimentary adult beverage for each guest
  • Guests can bring their own beverages
Additional Information

Free beer! Free pizza! A complimentary ticket to Boston’s top comedy club! And Boston’s most hilarious tour guides! The Massholes offer the best tour in the world’s greatest city! Have we traveled anywhere else? No. Do we have what they call “book learning?” Um, no. How can we so confidently make that claim? Well, you’re vacationing here, right? See? We’re both wicked smart. We’ll take you through all the best parts of this nearly 400-year-old city! We’ll stop halfway through for a break at one of the best comedy clubs in the country (with complimentary pizza!) You’ll hear about the Puritans, Tom Brady, the Molasses Flood, all the best stories told by the only authentic, original, legit Bostonian tour guides in this city, the Massholes!

Location
Asylum CoLab
Nestled in Boston's historic Faneuil Hall Marketplace, the CoLab is on the second floor, above the Crocs store, directly across from Ned Devine's at the southern edge of the Market.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(40 Ratings)
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Cara_t
Jul 11, 2024
Great fun! - What a great, fun, way to see Boston. Definitely recommend this trip. Nice balance between fact and fun and the pizza was yummy! Hosts are fantastic :-)
Review provided by Viator
752joshs
Jul 10, 2024
Wicked Fun Time! - We had lots of fun, plenty of laughs. 10/10 would go again and highly recommend! If you want to laugh take this tour plus you get a free drink and a taste of boston pizza!
Review provided by Tripadvisor
Alexc9885
Jul 6, 2024
Comedy on Wheels With a Touch of Drunk History - The Massholes Live Comedy Tour is a fantastic evening of comedy that highlights the best of Massachusetts humor. If you’re looking for a night filled with laughter, relatable jokes, and a touch of local flavor, this is the show to see. Highly recommended!
Review provided by Tripadvisor
Renee_o
Jul 5, 2024
Most fun evah.Boom! - Very personable, hilarious,, history buffs, concerned with our experience, checking in that we were having a good time and taken care of. From greeting to parting this is a must do while in Boston, this rocking trolley and crew are the best
Review provided by Viator
Brian_p
Jul 4, 2024
Boston Family laughs - The guides on our trip were awesome! Made the trip and experience so much fun. We had a small group and they made the most of our experience laughing all the way through the tour!
Review provided by Viator
Jaxi217
Jun 29, 2024
Great Tour Guides (Funny, Knowledgeable, and Kind) - This was a ton of fun. We learned some cool facts and saw some great Boston neighborhoods. The tour guides ere a great combination of funny, knowledgeable, and kind., Also, yummy pizza, and you can drink on the bus!
Review provided by Tripadvisor
H7775xijoed
Jun 23, 2024
Hilariously Fun Tour of Beantown. Oops I mean Boston - The tour was amazingly funny right from arriving at the Improv Asylum. Had complimentary drinks and informal introductions. We felt very welcome and the fun started right from the beginning. We took a few tours while on a cruise from Montreal to Boston and while they were informative they were nowhere as enjoyable as this tour.They combined historical info in a hysterical manner. All of the crew were great but specifically Mickey and Donnie. We highly recommend taking this tour. Non stop laughing and informative. Also they gave us a great recommendation for dinner. It was perfect.
Review provided by Tripadvisor
Colinl451
Jun 17, 2024
A Comedy Club On Wheels - My wife had suggested this to me as something that I might like as a counterpoint to all the serious historic stuff that we’d likely be experiencing whilst in the city. To be fair I was ambivalent about the prospect, but in reality it turned out to be a really fun night. At reception we were given a glass of fizz and told that as the trolley bus we’d be riding this evening was essentially stolen, the two comics/guides for the tour didn’t want to know our real names in case we were stopped by the police! And so it was that for the whole night I was James Bond and my wife was Moneypenny. The trolley followed much of the Freedom Trail, though not entirely, and part way through we stopped for a beer and pizza. It was pretty much a comedy club on wheels with audience participation and we loved it.
Review provided by Tripadvisor
Chrystal_n
Jun 15, 2024
Must do! - Amazing tour! Great way to learn about Boston while also laughing your butt off!!!! Mickey and Donny were HILARIOUS. Must do in Boston 👍👍
Review provided by Viator
Sharon_w
Jul 8, 2024
Loads of fun! - Donny and Mickey were so much fun. I don't know what I expected but I really enjoyed the style of humor and was surprised to learn some Boston history and info . I actually got to see and hear about places I had missed on another tour. Online Description of "pizza and drinks were not really very clear ( timing and amounts). More like an appetizer than a meal. We didn't count on needing dinner afterwards. Finally, because we were worried about the weekend after the 4th crowds , we purchased tickets ahead of time( and ended up paying 2 x the amount of cost same day purchase at the kiosk ( with discount night before the tour) on the same day, 2 hrs before the trolley tour. Worth it just for the entertainment.
Review provided by Viator
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September 2024
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