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 with co-owner Bob Sullivan, Sag Harbor Sailing now boasts hundreds of graduates from its award winning sailing education programs; and its fleet of well maintained twenty-three foot keel boats have plowed thousands of miles of water from the Hamptons’ Twin Forks, out around Shelter Island to Block Island, Newport, RI and Mystic CT and Montauk NY.

Students from age eight to eighty have graduated to solo sailing from private and group instruction. Summer camps are full of happy kids and familes 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 sails for for a destination of your own choosing?  Many boat owners now have websites and for a fee, will take you for a ride on their vessel, but before you go, please ask them if they are USCG licensed, ASA certified or even insured. Twenty years of experience does makes a difference.