Incredible sailboat rentals in Massachusetts, United States.
1 - 18 of 26 listings
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
25' Catalina Classic Pocket Cruiser "Double Diamond" Sailing Yacht Charter with Captain Mike in Providence, 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.
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.
- VF
Venus
103’ Trilogy Power Mega Yacht Harbor and Islands Charter
This yacht is completely gorgeous head to toe! The crew members were wonderful and really went out of their way to make sure we were comfortable and having a good time. We had the best time ever, it was the perfect birthday experience! Above and beyond!
- IO
Ifeoma
103’ Trilogy Power Mega Yacht Harbor and Islands Charter
I had such a wonderful experience celebrating my birthday. The crew was extremely helpful and so kind. I would definitely book again! I had so many friends and family inquiring about this boat. Thank you so much for the amazing experience and for making my birthday special.
- MF
Michelle
103’ Trilogy Power Mega Yacht Harbor and Islands Charter
Had a blast! Very comfortable for kids and Adults. The crew was extremely accommodating and made it that much better. Owner was helpful with all questions and even brought a wagon out to our car to carry our things easier. Sunset was beautiful. Crew had our drinks on ice and music bumping! Only downfall..my husband now wants to buy a yacht!
- BM
Brian
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
such an incredible experience. tony was an excellent host and captain. the boat was beautiful as was the scenery while we sailed. tony was attentive, funny, and communicative during the entire process. i would highly recommend him and Affinity" to all. you will not be disappointed.
- EO
ERNESTO
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
The Captain contacted me immediately after i posted my interest on the app. Exchanged a couple of messages and i arranged the payment through the app, which was efficient and secure. The day of the sail we were met right on time and took only a short walk to get on the boat. Once we were aboard we sit back and enjoy the sail. We felt very comfortable and,above all, we felt safe as we knew we were in the good hands of an experienced sailor, which also happened to be a very friendly and interesting person. No doubt I will sail with him on my next visit to Newport.
- MG
Marleiz
42' Sailboat "J/42 Affinity" Cruising Monohull Sailing Charter in Newport, Rhode Island
Anthony and his partner were amazing and so accommodating!! Our time was so fun- filled with stories and a wonderful time. You can bring snacks and drinks too!! Would definitely recommend over a sailing excursion if you want more of a private sailing experience especially with covid still going on! Thank you for a wonderful time, Anthony!! We will sure be back!