The Best Sailboat Rentals in Massachusetts

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Capt. Mason and Capt. Lynne are ABSOLUTELY AWESOME. Their 42' sail boat was incredible and my party of 5 had a fantastic time on our charter. They are knowledgable, accommodating and true sailors through and through. My wife and I HIGHLY recommend Capt. Mason for any charter needs you may have, using his yacht or any other!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Mason and Lynne were amazing captains on a private sail charter! So easy to communicate with throughout my planning process and amazing people overall! Had a great time being on the boat with them! Would absolutely recommend them and this experience!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.

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

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!!!

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!