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Great sailboat rentals near Oak Bluffs, Massachusetts.

Average of 3 reviews in this area.
3 listings

Step onboard a sailboat for an unforgettable experience in Oak Bluffs, Massachusetts.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Oak Bluffs, 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. Oak Bluffs, Massachusetts 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.

GetMyBoat customer reviews for Sailing in Oak Bluffs.

  1. 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.

  2. 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!