Sailing in the Hamptons, Since 1997

Go sailing in the Hamptons on the calm back bays of the East End. Sag Harbor Sailing has taught beginners and seasoned sailors here since 1997. Drive in, take the helm, and set off across protected water. Book a lesson today or call (631) 725-5100.

Most Hamptons schools teach on the open Sound or the ocean. Our Hamptons sailing school sails the sheltered bays around Sag Harbor instead. The water is calmer here and the wind is steadier. That makes your first sail easier and far less nerve-wracking. It is also a beautiful place to learn, with Shelter Island and the North Haven shoreline in view.

Sag Harbor Sailing started in 1997. Jim "The Commodore" Tompkins began with a few boats and one simple idea. He wanted people to sail the boat themselves. His son Mark runs the school today. We are accredited by the American Sailing Association. Our captains are licensed by the U.S. Coast Guard. Most have more than 20 years on the water. Students from age 8 to 80 and up have learned with us. Hundreds have earned their ASA 101 certification right here.

We teach total beginners and rusty returners alike. Private lessons give you the captain's full attention. Group classes run three times a day. The two-day ASA 101 course gets you certified to skipper a 23-foot keelboat. Every lesson is hands-on. You steer and trim the sails from the start. By the end of a few sessions, most students can rig the boat, leave the dock, sail a course, and bring it back in. If you want a clear path, this is it. Take a lesson, earn your ASA 101, rent a boat, then sail all season as a member. Ready to begin? Explore our sailing lessons in the Hamptons.

Younger sailors have a spot too. Our youth summer program runs for ages 9 to 16. Sessions meet on weekday mornings in July and August. Kids learn to sail and try a range of water sports along the way.

Already know your way around a boat?
Rent a 23-foot Pearson Ensign by the day. Sail it yourself, or bring a USCG-licensed captain along. The Ensign is a stable keelboat. It seats up to 6 people and has a head on board. Every rental includes life jackets and safety gear. Rentals start at $475 plus fuel, staff and gratuity. You can sail to Shelter Island, North Haven, or out into Peconic Bay. See all of our Hamptons sailboat rentals. Nowhere else in the Hamptons can you drive in, park for the day or overnight, take the helm, and pick your own destination.

Where can you go?
It depends on your time on the water. In a half day you can reach Shelter Island or cruise the North Haven shoreline. A full day opens up Peconic Bay and the Twin Forks. The bays stay calm and scenic the whole way. You will not face open ocean swell here. Pack a cooler and sunscreen, and wear soft-soled shoes for the deck.

Want to sit back instead?
Book a sailboat charter for up to 6 guests. It costs a fraction of a crewed yacht. You can help sail or just enjoy the ride. Your captain knows these waters and can teach as you go. Ask about our sunset cruises from May through September.

Sail often?
The Commodores Club pays for itself once you sail three or more times a season. Members get reduced rates and Yacht Hampton amenities all summer. Fortune 500 companies book us for team-building regattas too. Groups of every size sail with us, from couples to company outings. Learn more about the Commodores Club.

Sailing in the Hamptons should feel easy and welcoming. We sail out of the Yacht Hampton Boating Center at 51 Pine Neck Avenue in Sag Harbor. The season runs May 18 through September 30. Read our story since 1997. Call (631) 725-5100 to book your spot on the water.