The Massholes Comedy Trolley Tour

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

Duration: 2 hours
Cancellation: 24 hours
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!
    -…
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?…

Location
1643 John F Fitzgerald Surface Rd
John F Fitzgerald Surface Road
The Masshole Info Booth is nestled within Boston’s historic Faneuil Hall Marketplace. Steps from the Rose Kennedy Greenway, the info is directly across from Clarks Shoes, around the corner from the Crocs Store and Ned Devine’s.
Cancellation Policy

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

Customer Ratings
4.8
(73 Ratings)
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Tricia_n
Nov 2, 2024
Must try! - Trolley opened up with a song about massholes and I instantly knew I made the right decision to buy this experience. Throughout all the history the massholes made sure we were laughing and having a great time! For both locals & tourists I would highly recommend this ride.
Review provided by Viator
Kathy_b
Nov 2, 2024
Best trolley tour - Loved the singing and historical interpretations . Fun getting name tags too! OMG pizza was SOOO good! Definitely recommend to others
Review provided by Viator
K7506ximaryt
Nov 2, 2024
Take the trolly! - Great time from check in until the end, definitely recommend, I think a day time would be better, but Boston is beautiful at night. Jimmy & Johnny were awesome! Thank you so much!
Review provided by Tripadvisor
Melissaou6111em
Oct 23, 2024
Massholes of Boston - Soooo funny! We loved this tour and our guides and the pizza! We laughed from start to finish. Easy to find the stand where you start
Review provided by Tripadvisor
Ashleigh_s
Oct 21, 2024
Can’t wait to come back - I was expecting this tour to be great and it was even better than what I had expected. Devastated that it won’t be running when my family is here over the holidays. Can’t wait to bring them back sometime in the future.
Review provided by Viator
Patricial_s
Oct 19, 2024
Entertaining Tour - Best entertaining tour of a small bit of Boston. The tour guides were very engaging with the entire group, making us feel comfortable. Recommend highly! Starting entertaining your we were provided with a Modelo, not Boston beer, but it was a fun conversation piece. At the half point we stopped at their comedy club and ate a slice of pizza. Thank you for the entertaining tour!
Review provided by Viator
Melanie_o
Oct 16, 2024
Highlight of our Boston Trip - Truly the highlight of our Boston trip. On an hour and 45 minute trip we laughed for an hour and 30. The other 15 minutes we were filling our face at the pizza stop. Absolutely can not recommend enough!! - Slotz and Slutz
Review provided by Viator
Katiefm6621pl
Oct 15, 2024
INSANELY ENTERTAINING.... - OMG THIS WAS AMAZING. Not only were the nametags priceless......it was just beyond entertaining. These 2 cousins are so impressive. I learned a lot about Boston in the most enjoyable way possible! Thank you for your hospitality and just straight fun!
Review provided by Tripadvisor
Marcia
Oct 28, 2024
Funny comedy tour! - Fun times and the cousins had lots of energy! We enjoyed the bits of history and improv! Traffic in the city is horrible but it's Boston and we all know that!
Review provided by Tripadvisor
Voyager32208782591
Oct 20, 2024
Not so serious - The hosts were funny and worth the time! Definitely recommend for a light tour of the city. If you are looking for a history tour, this is not for you.
Review provided by Tripadvisor