Boston Travel Guides (Updated September 2026)

Enjoyed our guides. Trolley changed and included Hambone (our favorite), Bandit and I can’t remember the third gentleman. All very pleasant and informative.

Fabulous tour with Tyler who was engaging and incredibly knowledgeable -- we highly recommend this tour and this particular tour guide!

We had Jeremiah Poope as our guide. He was fantastic. He was informative, funny and very knowledgeable.. I would highly recommend this tour.

Tyler absolutely killed it as a tour guide. This guys interest in the history of Boston was palatable, his stories interesting and the views were bar none.As a guy doing my first solo trip, in Boston of all places, Tyler made it fun, interesting, and totally worth my time. He knew the crowd, planned for the windy weather, and somehow kept an eye on the traffic!Highly recommend the tour and as someone from Chicago that is familiar with a lot of tour guides, I’d totally recommend this guy as a guide for any of my friends or family visiting in the future. Can’t recommend enough.

The tour was fun and very informative! We learned quite a lot about Lexington and enjoyed the sights in Concord.

Informative and historical! Our guide was so knowledgeable about Boston history, the walk was easy and fun.

The tour was very well organized in how many stops were made. The Guides all had their individual characters but all were knowledgeable. I would recommend this tour for first time visitors to Boston.

Good guide & driver. A delightful experience. I will not enter characters just fill space. Shame on you, Cool Destinations.

The team who puts on this tour is amazing. Right from approaching them on the sidewalk to on the trolley. Lots of fun, well worth it.

Lots of fun. Good view of Boston harbor. Crew was very knowledgeable and friendly. Bring a jacket since it got a little chilly.

Our tour of Harvard was excellent. A real historical view of the University coupled with an interesting reflection of the students and its/their accomplishments. First rate!

John Hancock taught us a lot on this tour. I enjoyed hearing the stories that you don't learn about in school. I understand more about the important events that shaped our country plus interesting color commentary that kept our attention.

It was a great day and narrator was great. So informative and funny made it very enjoyable…. Driver was excellent.

Very informative and the perfect amount of walking. A lot of information was given that I did not know before. Our guide, Kile, was awesome!!! Can’t say enough about his knowledge and the way he explained information. So good!

Very much liked the reenactment of what happened on that fateful December 16, 1773 night. My grandson loved throwing the tea overboard to cheers! Great experience!

Anthony wasgreat. Tons of delicious food! Funny and down to earth! I suggest bring a couple of ziplocks! So you are not stuffed by the end! Great experience!