Old Town Trolley Tours

$20 for a 17-Stop Trolley Tour of Boston ($36 Value)

Up to 44% Off
550+ bought

What You'll Get

Jump to: Reviews | Trolley Alternatives

Not since Mr. Rogers first pulled on his sneakers has the trolley been a better way to explore. While his destination was the Neighborhood of Make-Believe, today’s Groupon will take you around Boston’s real-life puppet kingdom on an Old Town Trolley Tour. For $20, you’ll get one adult ticket ($36 value), which grants you all-day access to board and depart at any of the trolley’s 17 stops (listed to the right) whenever you please. Each trolley is toastily heated, making your tour comfortable any time of the year.

To begin your journey, hop aboard at the nearest stop. The stops are all conveniently located around Boston, finally allowing you to abandon your secret tunnel system as a means of getting to favorite sights. You can download a map to help guide you on your quest. Since there are a bevy of trolleys running the same route throughout the day, if you miss one, the next will be around within minutes, just like a carousel ostrich. Like their railed brethren, these vessels are highly reliable means of old-timey transport. Boarding is easy; the hard part is figuring out what sights to see and which activities to complete.

If you feel like doing your research, here is an online tour of stops, including recommended visiting times and descriptions. The highlights reel is too long to write about, but we’ve created a “best of” list. Pop into the New England Aquarium at stop one to satisfy all your oceanic needs. At stop 10, enter the Boston Skywalk Observatory, where your trolley ticket gets you $2 off admission to a 360-degree view of the city at 50 stories high. If you’re traveling with kids, the Boston Children’s Museum at stop 15 is a good place to burn off some excess energy, so the trolley can become a sleeper car on the way home. As you can see, there are more than enough attractions to occupy an entire day spent bouncing around Boston.

Don’t forget to thank your friendly and knowledgeable conductor, and get your inquisitive aunts and gung-ho guests in on this deal.


Past riders give the experience a four-star average on Yelp and give praising testimonials of their trolley experience:

  • We have just taken a trolley tour of Boston with a group of 7 people. I just wanted to let you know that your service is excellent and very professional as well as informative and fun. – J.J., Tampa, FL
  • I recently moved to Boston and had the family visiting from out of town. They ranged from 20 to 79 years old and EVERYONE enjoyed the tour. – S.B., Jamaica Plain, MA

Trolley Alternatives

For pure storybook romance, it’s difficult to top trolley, but that didn’t stop science from trying. Here’s a checklist of trolley alternatives, and how they clocked in on a 1-10 romance scale:

  • Komodo dragon: 6 out of 10
  • Ultra-dense amoebic swarm: 4 out 10
  • Segway cop: 2 out of 10
  • Giant centipede in tuxedo and tap shoes: 9 out of 10
  • Charles Barkley in a trolley costume: off the scale

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The Fine Print

Promotional value expires Nov 16, 2010. Amount paid never expires. Limit 1 per person. May purchase up to 7 additional as gifts. Valid only for adult ticket. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

About Old Town Trolley Tours

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