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The Massholes Comedy Trolley Tour of Boston | 2 hours

74 Reviews | Boston
From $49.00 per person Lowest Price Guarantee
Select Date and Travelers
You can select up to 10 travelers in total.
Adult (16-99) Minimum: 1, Maximum: 10
2
Free Cancellation For a full refund, cancel at least 24 hours before the scheduled departure time.
The Massholes Comedy Trolley Tour of Boston! Best in the city!
2 Adults x $49.00
$98.00
Approx Total
$98.00

Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English
  • Halfway through, we stop at the Improv Asylum Theater for some delicious North End pizza! Who doesn't love free pizza?!
  • Each trolley begins with a complimentary adult beverage for each of our guests! And you're more than welcome to bring your own!

Overview

Free beer! Free pizza! A free ticket to Boston's best comedy club! And Boston's funniest tour guides! The Massholes give the best tour in the world's greatest city! Have we travelled 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 almost-400-year-old city! We'll stop halfway through for a pitstop 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!

Meeting points

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.

End point

This activity ends back at the meeting point.

Itinerary

Sample Menu

Additional Info

  • Service animals allowed
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels

Free Cancellation

October 31100% refund
November 01No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Traveler Photos
Reviews

4.9

74 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    65
  • 4 stars
    8
  • 3 stars
    0
  • 2 stars
    1
  • 1 star
    0

Reviews by TravelOne travelers

Showing 1-5 of 65 reviews with 5 stars

Funny improv and all the sites of Boston

Published on Jan, 2025

We had a hilarious time touring Boston on their trolley. Comics did a great job of teasing people just enough to bring the group together. We brought our 13 year old and were not upset by the content being too mature, but we also appreciate opportunities to talk about material others might not. We saw lots of sights in the city we would have missed otherwise. They even provided a special gluten free pizza for me. Highly recommend!

Must try!

Published on Nov, 2024

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.

Best trolley tour

Published on Nov, 2024

Loved the singing and historical interpretations . Fun getting name tags too! OMG pizza was SOOO good! Definitely recommend to others

Take the trolly!

Published on Nov, 2024

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!

Massholes of Boston

Published on Oct, 2024

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

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