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About Us

Sag Harbor Sailing’s first year of operation was 1997. Co-owner Mark Tompkins’ father, Jim ‘The Commodore’ Tompkins, started with a few boats and a plan to provide the opportunity for customers to sail a boat themselves.

Twenty years later, Sag Harbor Sailing now boasts hundreds of graduates from its award-winning sailing education programs; and its fleet of well maintained 23-ft. keel boats have tracked thousands of miles of water from the Hamptons’ Twin Forks, out around Shelter Island to Block Island, Newport, RI, Mystic, CT, and Montauk, NY.

Students from age eight to eighty have graduated to solo sailing from private and group instruction. Friends and families can’t ask for a better way to gather and reunite. Fortune 500 companies rely on Sag Harbor Sailing to plan and execute team building regattas regularly.

Where else can a sailor drive in, park for the day (or overnight), take the helm, and set sail for for a destination of their own choosing?