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Sag Harbor Sailing’s first year of operation was 1997. Then 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. And, our Commodore Club members enjoy reduced rates and the amenities at the Yacht Hampton Boating Club all season long.

Located at the Yacht Hampton Boating Center at 51 Pine Neck in Sag Harbor, Sag Harbor Sailing is an excellent choice for anyone looking to learn to sail, improve their skills, or simply enjoy being out on the water. No where else in the Hamptons 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.