Incredible sailboat rentals in Massachusetts, United States.
1 - 18 of 36 listings
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
46ft Soubise Sailing Catamaran Boat Cruise in Newport, Rhode Island - Fully Booked will be available on September 3
Rent or charter a sailboat for a memorable experience in Massachusetts.
Are you ready for a fun adventure out on the open water onboard a sailboat in Massachusetts? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Massachusetts is a wonderful sailboat rental destination.
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Search for the perfect experience now and book your dream day out on the water.
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GetMyBoat customer reviews for Sailing in Massachusetts.
- AK
Alex
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
Tony is the special person that would make your journey totally unforgettable. Especially, if you have your kids with you. He is a great teacher and mentor for any ages! This is one of the memorable experiences you want to have in your life at least once to make it worthy!
- JH
Jeanne
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
Great two days on the boat with Anthony! He's a terrifically experienced captain and an interesting, fun, nice guy. A really patient teacher too, as we hoped to learn a bit more about sailing. Super accommodating, wanted to do whatever we wanted and was really invested in making sure we had a good time. Would definitely recommend to a friend.
- JM
Jamie
Experience Newport RI with us! - Charter "Hope San" Sailing Yacht
I can’t stress enough how amazing this was! First off Patrick and his wife were the best hosts/captains. They told us a lot about the area while we were sailing and they made sure we were comfortable the entire trip. The boat is beautiful! Also it being Labor Day Weekend it was nice to just have the boat to ourselves away from the crowds! We got to watch the sunset on the boat and it’s probaly one of the best sunsets we’ve ever seen. I would recommend this experience to anyone!
- AG
Angelique
Sailing Charters On 36ft "Emma Rose" Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations
We had such a wonderful time aboard the Emma Rose with Captain Allan! We took my father for his birthday, in May and had such a wonderful time! We were able to pack a picnic, and were able to get really hands on with the sailing, and learned so much! The trip was so relaxing and refreshing! My dad still talks about how wonderful that day was, and how much he learned! Captain Allan is great with communication before hand as well, and answered all our questions promptly! We had an amazing sail around the north shore and are looking forward to planning our next sail with Captain Allan! We would highly recommend!
- MQ
Matthew
Cruising Catamaran for Charter in Newport, RI
Kia and Al were the greatest team out on the water! We planned a fantastic day with them, and we would highly recommend booking with them! Their boat, Alykat, was extremely comfortable and spacious. They really went above and beyond to make it a special day. They were open to working with us on the experience we were looking for. Great charter all around!!!
- AP
Andrew
46ft Soubise Sailing Catamaran Boat Cruise in Newport, Rhode Island - Fully Booked will be available on September 3
Claude was friendly, knowledgeable, and very easy to get along with! He took our family (3kids 10-15yrs old) and showed them the ropes, took as out beyond the coast, and made a fantastic day of it- Highly recommend! Only regret would be not going for a longer trip, I think several days, even up to a week to explore the coast and really get the hang of it!