The Best Sailboat Rentals Near Boothbay

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. ⭐️⭐️⭐️⭐️

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!

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

From start to finish, Kenneth was incredibly friendly and engaging, making the entire experience unforgettable. He truly made us feel like part of the sailing adventure, sharing his knowledge and ensuring we had the best time possible. I would rate this experience a 10 out of 10 and would gladly book with him again next time we're in town. Highly recommend!

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

My husband and I booked this excursion with Mason and Lynn for the 4th of July weekend, and it was the best part of the entire weekend! Mason and Lynn were incredibly hospitable and caring, communicative, and thoughtful. Mason suggested taking the day to go to Cuttyhunk and it was worth it. We had the best lobster rolls of our lives and walked around the town. It was a magical day. The boat was beautiful and Mason and Lynn went out of their way to make sure we had a great day. Highly highly recommend!