The Best Boat Rentals Near Chilmark

Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht

We booked this boat for my bachelorette trip, and it could not have been more perfect! From the moment we stepped onboard, everything was clean, spacious, and exactly as advertised. The captain was friendly, professional, and made sure we had the best experience—he even knew all the best spots for swimming, cruising, etc. The boat had plenty of room for our group to relax, dance, and enjoy the sunshine. The sound system was amazing (a must for a bachelorette party!), and there was a cooler/fridge ready for our drinks and snacks. We loved that we could customize our day—whether we wanted to anchor and swim, explore the area, or just cruise around with music and laughter. It was the highlight of our trip, and every single person in our group said they’d do it again in a heartbeat. If you’re looking for the perfect mix of fun, relaxation, and gorgeous views, this is 100% the way to go. Highly recommend for any bachelorette or special celebration!

Ocean Oasis: Newport's 51ft Party Yacht for Unforgettable Coastal Soirées!

We had absolutely incredible time!!! We brought pizza and drinks (which were easy to keep cool because of the icebox on board), got to see some of the famous mansions, went swimming in the cove, and got amazing sunset pictures.

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!!!

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

Kenneth and his boat exceeded all expectations and we had a fabulous day. He was very engaging and informative, and made our day alternating between sailing and listening to music in front of the folk fest an amazing experience. He even anchored us right up next to the stage with expertly navigating between a ton of other boats. Can’t wait for next year and highly recommend.

34' Mainship Pilot Power Boat for charter with Captain in Newport, Rhode Island

Charles was an excellent captain! Made the experience very enjoyable and fun, very knowledgeable about the area and its history and provided a lovely evening cruise for us. The boat was fantastic and provided multiple seating areas and beverages, would gladly book with Charles again on another visit.

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!