Martha's Vineyard Travel Guides (Updated September 2026)

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.

Harry was a great tour guide he helped us get the trip was pleasant to listen to with much knowledge of the area. Never felt rushed and very comfortable travel van.

We were extremely satisfied with our tour on Martha’s vineyard. The driver was excellent. He was very informative. We have used Cool Destinations many times in the past and they have always been great

As a first time visitor to The Vineyard and only there for the day, this was the perfect way to see the island and hear some history by someone who actually lives on the island and was born and raised there. John, our guide was brilliant, very friendly and knowledgeable. We were lucky with the weather and the fact that it was after the labour day holidays so it was easier to get around and see things that can be difficult to during these periods. Definitely recommend.

We had an excellent 3 hour tour of Martha’s Vineyard! We learned a lot about the island and saw many beautiful sites. Would use this company again!

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.

We had an absolutely fantastic experience on our private Martha’s Vineyard tour! From start to finish, everything was seamless, relaxed, and so much fun! Having a private tour for our group of six was the perfect way to see the island without feeling rushed or having to follow a large group.Matt Taylor was an absolutely perfect guide - a very knowledgeable native, friendly, and clearly passionate about Martha’s Vineyard. We saw so much of the island and got to experience places and views we would have never found on our own. The tour was the perfect mix of beautiful scenery, interesting history, local insight, and plenty of time to enjoy each stop.What we loved most was the flexibility and personal attention. We could ask questions, take our time, and really enjoy the experience rather than constantly watching the clock. It felt like we were being shown around by a friend who knew all the best spots!If you’re visiting Martha’s Vineyard for the first time, I highly recommend this tour. It was honestly one of the highlights of our trip, and we would absolutely do it again. Five stars all around!

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.

We are a group of nine friends celebrating our 50th high school reunion. We are staying in Vineyard Haven but wanted to see more of Martha’s Vineyard, so we booked a private tour with Couri at Martha’s Vineyard Tours and Transport.Couri was knowledgeable, fun, and accommodating. She shared historical knowledge and personal anecdotes. Couri was a big help with one of our party who is temporarily using a wheelchair.To help understand the island better, start with a tour with Couri.

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!

We had 4hr island tour with Sam. Great fun. Sam is a native and had so many stories and insights to share. We highly recommend

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.