About Sag Harbor Sailing, a Hamptons Sailing School Since 1997

Sag Harbor Sailing has taught the Hamptons to sail since 1997. We are a family-run sailing school and charter operation on the protected bays of the East End. Our goal has not changed in all that time: get people out on the water, in their own hands, with an expert beside them. If you have ever wanted to learn, this is a welcoming place to start.

It began with one idea. In 1997, Jim "The Commodore" Tompkins started the school with a few boats and a simple plan. He wanted customers to sail the boat themselves, not just ride along. His son Mark, a co-owner today, grew up in that tradition and still runs the school by it. Many students come back season after season, and some bring their own kids to learn. Nearly thirty years later, hundreds of sailors have earned their certification with us. Our well-kept fleet of 23-foot keelboats has logged thousands of miles. Those trips have ranged from the Twin Forks around Shelter Island to Block Island, Newport, and Mystic.

We believe almost anyone can learn to sail. Students from age 8 to 80 and up have gone from their first lesson to skippering on their own. We teach on the calm back bays around Sag Harbor, not the open Sound or ocean. The protected water and steady wind make a gentler classroom, so beginners feel at ease and progress faster. It is a patient, hands-on approach, and it works.