The Massholes Comedy Trolley Tour of Boston

Planning a trip to Boston and looking for something that mixes a bit of history with plenty of laughs? The Massholes Comedy Trolley Tour offers just that—a lively, humorous ride through the city’s most interesting neighborhoods, with a healthy dose of comedy, good food, and local charm. Based on a flood of rave reviews and a perfect five-star rating, this tour promises a unique way to see Boston that’s as entertaining as it is informative.

What we love about this experience is how it combines authentic Bostonian humor with a manageable itinerary that hits many of the city’s key sites. Plus, the inclusive perks—free pizza, a free beer (or Modelo, if you prefer), and a ticket to one of the country’s top comedy clubs—make it quite a steal for just $39. However, keep in mind that this tour is pretty casual and humorous, so if you’re after a serious, in-depth history lesson, this might not be your cup of tea. It’s perfect for travelers who want a relaxed, humorous introduction to Boston, especially if you enjoy good storytelling combined with a bit of comedy.

Key Points

• The tour blends comedy, history, and city sightseeing in a fun, informal way.
• Guides are praised for their humor, authenticity, and engaging storytelling.
• The itinerary covers must-see sites like the Boston Massacre site, Paul Revere’s resting place, Bunker Hill, and more.
• The tour includes a pizza stop and free beer, adding to its relaxed, social vibe.
• Small group size (up to 14 travelers) ensures a more personalized experience.
• Good value for the price, with multiple reviews highlighting the entertainment and food quality.

An Overview of the Experience

From the moment you meet at 1643 John F Fitzgerald Surface Road, the tour sets a lively, informal tone. The guides, known as the “Massholes,” are Boston-born and bred—no cookie-cutter tour guides here. Expect humor, local slang, and plenty of laughs right from the start, including a catchy opening song about “Massholes,” which instantly signals this is no snooze-fest.

This trolley tour is about 2 hours long, taking you through nine neighborhoods and significant historical sites. The group remains small—maxing out at 14 participants—which fosters a friendly, intimate atmosphere where everyone feels involved. The tour is mobile ticketed, making it easy to join and convenient for travelers with tight schedules.

The Itinerary: What You’ll See and Do

The itinerary is well-chosen to give you a taste of Boston’s most notable spots, but with a playful twist. Each stop offers a mix of story, humor, and scenery:

• The Boston Massacre Site: Here, you’ll hear the story of a pivotal moment in American history—told with a humorous edge that keeps things lively. It’s a quick but impactful stop that sets the tone.

• Paul Revere’s Resting Place: You’ll pass by the final resting spot of patriots like Revere, Sam Adams, and Hancock. The guide’s storytelling makes these historic graves come alive, blending respect with humor.

• Boston’s Swankiest Address: Since the 1880s, this neighborhood has been a symbol of wealth and sophistication. Expect tales of old Boston opulence mixed with amusing anecdotes.

• Entertainment Hub: The tour stops at Boston’s premier entertainment district, home to theaters from Broadway to comedy clubs. It’s a reminder that Boston is still a city of vibrant arts.

• Chinatown: The bustling, colorful neighborhood offers a glimpse into Boston’s most diverse community, with stories and food options that make this stop memorable.

• Waterfront and Rose Kennedy Greenway: The Big Dig’s transformation of Boston’s landscape is on full display here, with scenic views and stories about the city’s evolution.

• Historic Charlestown: The neighborhood of Bunker Hill and the USS Constitution anchors history buffs, with tales of naval battles, warships, and Boston’s oldest neighborhood.

What to Expect at Each Stop

Each location is presented with a lighthearted approach, making history fun and accessible. The guides excel at balancing humor with respect, ensuring that the stories resonate. Travelers consistently mention the guides’ engaging personalities and their ability to make history feel relevant and funny. Expect to learn, laugh, and occasionally be surprised by local lore you might not find in a textbook.

Food, Drinks, and Extras

A notable highlight is the half-way pizza stop. Reviewers rave about how good the pizza is—some even describe it as “SOOO good.” It’s a relaxed break that lets everyone mingle and refuel. The tour also includes a free beer, which is a nice touch, especially after some hearty laughs and sightseeing. If beer isn’t your thing, the guides are accommodating, and service animals are welcomed.

The ticket also includes a free entry to Boston’s top comedy club. This added value is a big draw, allowing you to continue the night’s fun well beyond the trolley ride. The comedy is a mix of standup and local humor, often delivered by guides or comedians with Boston roots, adding that authentic flavor that visitors love.

The Guides and Atmosphere

Reviewers consistently praise the guides for their humor, knowledge, and friendly attitude. They’re described as “wicked smart” in a Bostonian way, capable of mixing history with jokes effortlessly. The guides’ local slang, nicknames, and engaging personalities make the experience feel personalized rather than scripted.

The small group size creates an inclusive environment, where everyone feels comfortable participating in jokes and stories. It’s clear that the guides thrive on audience interaction, making each trip feel like a casual night out with friends who happen to know a lot about Boston.

Pricing and Value

At $39 per person, this tour is a strong value for what you get. For less than the cost of a fancy dinner or a couple of drinks, you get a lively two-hour ride, good laughs, a slice of pizza, a free beer, and a ticket to a comedy club. Several reviews highlight the high entertainment level, good food, and personable guides as making this a worthwhile spend.

It’s especially appealing for travelers who want to see Boston from a fun perspective rather than a stern history lesson. The inclusion of food and drinks, along with comedy, means the experience feels like a laid-back social outing rather than a structured tour—and that’s part of its charm.

Practical Details: Logistics and Tips

The meeting point at John F Fitzgerald Surface Road is easy to find, near public transportation options. The tour’s duration is about 2 hours, making it a manageable activity for most travelers—especially if you want a break from museums or walking tours.

Since tours operate with a maximum of 14 travelers, you’ll likely feel like part of a small group rather than just another face on a bus. Booking in advance is recommended, especially during peak seasons, and cancellations are free up to 24 hours before the tour.

Weather can influence the experience—if it’s bad weather, the tour might be canceled, with options for a new date or a full refund. Be prepared for Boston’s sometimes unpredictable weather, and dress comfortably.

This experience is best suited for those who enjoy a laid-back, humorous approach to sightseeing. It’s perfect if you’re traveling with friends or family who appreciate comedy and storytelling more than rigid history. If you’re looking for a fun way to see multiple neighborhoods in a short time, with plenty of laughs and good food, this tour hits the mark.

It’s also excellent for first-timers in Boston wanting an authentic, local perspective, as guides are full of stories and jokes you won’t find in conventional guides. If you’re a fan of comedy clubs and local humor, the included ticket to Boston’s top comedy venue makes this a very attractive choice.

However, if you’re seeking a deeply detailed, serious history tour without humor, you might prefer a different experience. This tour is casual, humorous, and designed for fun, not for education in the traditional sense.

The Massholes Comedy Trolley Tour offers a unique way to experience Boston, combining history, humor, and good eats into a lively package. Its small-group format, engaging local guides, and inclusive extras—pizza, beer, and a comedy club ticket—make it a fantastic value. It’s perfect for travelers looking for a relaxed, fun introduction to Boston’s neighborhoods and stories, especially if they enjoy humor and casual social atmospheres.

While it doesn’t replace a traditional historical tour, it excels at making city sightseeing lighthearted and memorable. Expect plenty of laughs, authentic Bostonian banter, and a chance to see some of the city’s most iconic sites in a way that’s both entertaining and personal.

If you want a lively, genuinely Boston experience with a comedic twist, this tour will meet and exceed your expectations. Just remember to bring your sense of humor and your appetite for pizza and laughs.

FAQ

Is the tour suitable for all ages?
Most travelers can participate, but the humor sometimes includes adult language. If that’s a concern, check with the guides beforehand.

How long does the tour last?
The tour runs approximately 2 hours, including stops and the pizza break.

Is there a limit on the number of travelers?
Yes, the tour accommodates up to 14 travelers, ensuring a small, friendly group.

What’s included in the price?
Your ticket covers the trolley ride, a slice of pizza at the midway stop, a free beer (or Modelo), and a ticket to Boston’s best comedy club.

Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours before the tour starts.

What is the meeting point?
The tour begins at 1643 John F Fitzgerald Surface Rd, Boston.

Is this tour accessible for service animals?
Yes, service animals are allowed.

How does the comedy club ticket work?
It’s included in your ticket—just show your voucher to enjoy a night of comedy after the tour.

Is the tour family-friendly?
Generally, yes, but be aware that humor can include adult language, so discretion is advised for children.

What’s the main appeal of this tour?
The mix of humor, local stories, and a relaxed atmosphere makes this a memorable, entertaining way to see Boston.

In short, the Massholes Comedy Trolley Tour delivers a lively, humorous, and authentic Boston experience that’s hard to beat for value and fun. Perfect for those who want to see the city’s highlights without the stiff formality—just a good time with good stories.