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United StatesMassachusetts

Incredible sailboat rentals in Massachusetts, United States.

Average of 33 reviews in this area.
1 - 18 of 34 listings
34 results

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.

Using GetMyBoat to book your next sailing experience.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Massachusetts.

  1. 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!

  2. 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!

  3. 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!

  4. 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.

  5. 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!

  6. TT
    Terry
    Private Charter on 41ft "Dream Catcher" Lagoon 410 Sailing Catamaran in Vineyard Haven, MA

    I highly recommend Steady As She Goes Charters. Our group of 13 people including 7 kids had a great time and everything went very smoothly. They were also very accommodating with finding an alternate date when our originally booked date was rained out.