Chilmark, Massachusetts Boat Rentals

Chilmark Reviews

1. 

   Rodney

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip

2. 

   Dhuvi

   Yamaha 195S Wakeboat in Sandwich MA

   If this is the only review you read, all you need to know is that you wont find a better boat or boat renter. The 195s is an insanely fun ride and very beginner friendly (rare combination) and Caleb has excellent communication and is super accommodating. Youd be hard pressed to find things that could have made our experience better.

3. GE

   Gerald

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   By far the best part of our trip to Martha’s Vineyard and the highlight of my girlfriend’s birthday was our time on Captain Mason and Captain Lynne’s boat. They thought of every detail, including birthday decorations and helping me with multiple surprises, took us to the most beautiful spots along the coast and harbor, and even let us partake in a super unique light show boat parade experience. This is by far the best value for money and most unique and relaxing / beautiful experience you could have in the Vineyard. Please trust me and book! Mason and Lynne are also wonderful people who really try to make your experience as amazing as possible. Thank you so much for everything!!!

4. JK

   John

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   I don’t usually write detailed reviews, but this experience definitely deserves a shoutout. Capt. Mason and Capt. Lynne were incredibly responsive from the moment I submitted the reservation request. I was planning to propose to my girlfriend of 10 years during the sail, and they went above and beyond to help make it perfect. We now have an extremely loved memory that we will cherish for our whole life. Even when I had to make some last minute changes, they were super flexible and understanding. To anyone reading this—if you’re looking for an unforgettable experience with your loved one, this is it. Book it!

5. RR

   Robyn

   36' Classic Powerboat Rental In Newport, Rhode Island

   Absolutely perfect evening on the water! The short sunset cruise was the highlight of our trip—smooth sailing, stunning views, and a relaxed vibe. The captain was knowledgeable and friendly, and the deckhand made sure everyone was comfortable and had what they needed. Truly a five-star experience—we’d book again in a heartbeat!

6. AB

   Amanda

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   My family and I had a spectacular sailing adventure. Mason and Lynn are friendly and professional and really made us feel welcome. They gave us an experience that we will never forget. The boat had plenty of room for all of us to enjoy sightseeing and even allowed some on board fishing. We had never sailed before and after our time with Mason and Lynn, we can’t wait to sail with them again. If you’re looking for an unforgettable time on the water, I recommend sailing with them. ⭐️⭐️⭐️⭐️