Incredible sailboat rentals in Massachusetts, United States.
1 - 18 of 33 listings
Charter 50ft "Frayed Knot" Cruising Monohull In Manchester-by-the-Sea, Massachusetts
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
Private Charter on 41ft "Dream Catcher" Lagoon 410 Sailing Catamaran in Vineyard Haven, MA
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.
Top destinations nearby
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!
- 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!
- 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!
- MR
Morgann
Private Charter on 41ft "Dream Catcher" Lagoon 410 Sailing Catamaran in Vineyard Haven, MA
We always have such a blast with Captain Gary and Firstmate Jane. It has become an annual tradition. Can’t wait to explore MV with them again next year!
- LD
Lisa
City Tour in Boston
Peter was an excellent captain and made my husband's 60th birthday sail fantastic! Peter helped me organize food and drinks for the trip and customized our day based on what my husband wanted. Highly recommend this boating experience!!
- MB
Matthew
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
Captain Tony was completely accommodating from my initial inquiry right through to waiting for us to return to collect my daughters hat she accidentally left behind. A fabulous day, we will definitely refer our friends and return ourselves!