The Best Sailboat Rentals Near Ashland

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.

43' Sailboat, Bristol RI & Beyond

We had a delightful afternoon sail with Captain Francis! He was skilled and easygoing and his boat was very well equipped. Two of us were experienced sailors and he graciously allowed us to help crew and take the helm as much as we wished. We all shared stories of past adventures and had a wonderful day in Bristol and Narragansett Bay. Highly recommended!

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!

43' Sailboat, Bristol RI & Beyond

We had a wonderufl afternoon sailing on the bay with Captain Francis! Our kids had some prior sailing experience, and he was kind enough to let them crew a bit. He was personable and knowledgeable, we had a great time, and would definitely book through him again!

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. ⭐️⭐️⭐️⭐️