SAILING LESSONS, RENTALS & YOUTH CAMPS IN THE HAMPTONS

Sag Harbor Sailing has been on the water since 1997. Jim 'The Commodore' Tompkins started the school with a few boats and a simple idea: anyone should be able to sail in the Hamptons, captain or no captain. Today the school is run by his son Mark Tompkins and partner Joe Ialacci, with USCG-licensed captains and instructors who have 20+ years on the water. We're an ASA-accredited school based at the Yacht Hampton Boating Center at 51 Pine Neck Avenue in Sag Harbor, NY. Hundreds of students have earned their ASA 101 certification with us. We work with families, couples, corporate teams from Fortune 500 companies, and total beginners — ages 8 to 80+.

Our fleet of 23-foot Pearson Ensign sailboats can carry up to six people. Sail with one of our captains and learn as you go, or take the boat out yourself if you've got the experience. Half-day, full-day, and sunset cruise options are available from May 18 through September 30. Sail to Shelter Island, around North Haven, or out into Peconic Bay — the East End is one of the most beautiful cruising grounds on the East Coast.

If you sail with us three or more times in a season, the Commodores Club membership pays for itself. Members also get access to amenities at the Yacht Hampton Boating Center.

We teach sailing the way we wish we'd been taught: one boat, a small group, an experienced instructor, and real wind. Private lessons take up to four students per session. Group classes run three sessions per day from May 18 through September 30.

Beginners can earn their ASA 101 Basic Keelboat certification through our two-day intensive course. Once you've got 101, we offer intermediate keelboat cruising instruction (ASA 103/104) for sailors who want to take the next step toward bareboat chartering.

Every instructor has 20+ years on the water. Every certification is recognized worldwide.

Our youth summer program runs Monday through Friday, 9:00 AM to 12:00 PM, from July 1 through August 30. Kids ages 9-16 spend the week sailing, wakeboarding, tubing, water skiing, fishing, paddleboarding, riding SEABOBs, swimming, and even learning to captain a boat. We mix structured sailing instruction with the kind of summer day that makes kids ask to come back next year.

Spots fill up early — most weeks sell out by May. Book by week, not by the day.