Massachusetts 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.

Excellent and knowledgeable crew. All the other guests enjoyed. Lovely views. Had an amazing time!!!

Heidi was engaging, education, funny, and passionate. The stories came alive with how she was telling them and her consideration for everyone in the group, and friendlines was infectious. I highly recommend!!

Our tour guide Duncan knows his stuff! Having a guide that grew up and lives on Martha’s Vineyard is a major plus. Would highly recommend this tour for anyone.

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.

We had Henry for our guide ! He was excellent ! Very knowledgeable and made the tour very interesting ! The time Went by so quickly ! We enjoyed every minute !

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.

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

A perfect way to experience Salem. The crew was friendly, experienced and helpful. The boat was amazing, and a wonderful addition to our girls trip weekend. The views were beautiful! Awesome trip, and I would definitely do it anytime I came to visit.

Quite a bit of walking. The tour was great! Out guide was very entertaining. The stories and stops were very interesting

This is always worth the trip regardless of whether you see whales. We saw a small group of humpbacks feasting. They hung out around next to the boat. WILD. And the crew were great, they are so knowledgeable.