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Great sailboat rentals near Tisbury, Massachusetts.

Average of 3 reviews in this area.

Step onboard a sailboat for an unforgettable experience in Tisbury.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Tisbury. 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. Tisbury is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

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.

5 listings
15 guests

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

6 guests

Private Sailing Charter on Martha's Vineyard

6 guests

48' Schooner Sail Charter in Tisbury, Massachusetts

6 guests

15ft Sunfish Sailboat Rentals in Tisbury, Massachusetts

4 guests

Cruising Monohull for rent for sailing in Oak Bluffs, Massachusetts