Martha's Vineyard Travel Guides (Updated September 2026)

Duncan was our tour guide, he is very knowledgeable about the island. He explained everything very thoroughly and clearly. Definitely worth the the trip!

A great way to see the island and visited places you probably wouldn’t on your own. The tour guide/driver was very friendly , hospitable and knowledgable. Highly recommended.

Well planned - fabulously interesting tour. Our guide, Duncan, was EXTREMELY knowledgeable! A true historian- and he added many interesting personal side notes. A definite MUST tour.

Guide was very knowledgeable. He explained all the sites and history. Very courteous in answering questions.

This is a comfortable and thorough tour. Stan was a great tour guide, telling us stories about the history of the island and interesting residents. Having grown up in Martha’s Vineyard and with relatives still there, he has a lot of insight to the island.

Craig was a fantastic guide. He was in communication with us before we arrived so he knew the ferry was dropping us off at a different terminal than was the original pick up point. Had a great and informative 3 hour tour of the entire island. Vehicle was clean and comfortable. Craig was very friendly and we hope to see him in Myrtle Beach for a visit.

Craig is an excellent guide. Knowledgeable and humorous. My wife and I very much enjoyed our tour of Martha’s Vineyard. We were impressed with all the detailed information that Craig had to share. His vehicle was spotless and he drove safely.

I enjoyed this tour! This is the second time I purchased it; the first time was very confusing but this time it was great!

Very informative and enjoyable afternoon seeing various towns/historical sites on the island. I highly recommend if you are just there for the day. Loved hearing about the making of Jaws!

Really great idea! Loved going on our own time and pace. I wasn’t feeling well from over drinking the night before. I loved not having to be somewhere at a particular time. And we could take a break when we wanted. Great information and easy to use! Loved doing the walking tour app!!!

We thoroughly enjoyed our afternoon with Lisa. Unfortunately, the weather was not good and she did make changes. Took us in her truck and gave us a fantastic tour with the bikes in the back. We stopped at the seafood pier and had lunch in the car. It was amazing. And then we drove to Edgar town at that point. We were able to unload the bikes and have a fantastic ride to Oak Bluff. She accommodated us and made it the best excursion ever. Thank you, Lisa.

The vehicle was a standard minivan - not a luxury van at all by most standards. There was just enough room for 5 people assuming no walker or wheelchair.We booked the two-hour tour for 5 adults. One was my 91-year-old mother who uses a walker. Luckily the 5th person made other plans or there wouldn’t have been room for the walker. The driver noted he had expensive electronic equipment in the storage area.Our guide was knowledgeable about the general history of island. He shared a few interesting facts during our tour of Vineyard Haven and Edgartown. However he seemed clueless about the history of African Americans on the island with the only exception being to point out the road leading to the Obamas’ house.Overall I would rate the tour a 6 out of 10.

Lisa has great bikes, is kind and easy to work with, has lived on the island for 30+ years, and gives a good tour. Plus, we needed up riding 30+ miles, but that’s not too hard with an e-bike.

The personalized tour allowed opportunity to ask questions, see the island from a tourist and community member perspective.

Great tour for everyone but especially new people to the island. Learned a lot and it was a great informative day. Bart is an excellent tour guide.

Our trip to Martha’s Vineyard was cancelled due to weather. Cool Destinations and vendor were gracious about refunding our money.