The Best Sailboat Rentals Near Whitefield

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. ⭐️⭐️⭐️⭐️

42' Catalina Sailing Yacht in the Hamptons

We are so happy we chose to book with Nate! The communication was clear and concise, we knew exactly where to go when our trip came! Nate and crew were beyond accommodating and the boat is so charming! This made our trip so special!

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

Capt Ken was fantastic - highly recommended for small groups especially with kids. Ken was super communicative leading up to the trip, and provided a custom experience (finding a good spot to swim), he even let the kids steer the boat. The Mariah is a beautiful vessel with comfortable seating as well as roomy and shady as needed. I would book with Ken again no questions. Thank you, Ken!!

Charter 36ft Sloop In Westbrook, Connecticut

We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!