SAG HARBOR SAILING

Rentals, Lessons, Charters and Summer Youth Programs

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EXPLORE SAILING LESSONS, RENTALS AND YOUTH PROGRAMS

Sail the Hamptons, home to some of the world's most beautiful waterways

Three people sailing a boat with blue and white sails alongside a second sailboat on open water with Sag Harbor Sailing
SAILING BOAT RENTALS

Our 23-foot Pearson Ensign sailboats can comfortably accommodate up to six people. Whether you choose to sail with a captain or on your own, you can fully enjoy your time on the water.

Additionally, our Commodores Club offers seasonal savings for those who sail more than three times.

Two people handling the rigging aboard a sailboat on a bright, breezy day with Sag Harbor Sailing
LEARN TO SAIL

Our instructors offer private lessons on our company’s fleet of 23-foot Pearson Ensign sailboats. Each private lesson can accommodate up to four students, ensuring attention and effective learning.

Get certified with our 2-day American Sailing Association beginner sailing certification program.

Two boys wearing life jackets and swim trunks jump off the back of a motorboat into a wide, sunny lake.
SUMMER YOUTH PROGRAM

Week‑long program includes diverse water adventures such as sailing, wakeboarding, tubing, water skiing, fishing, paddle boarding, SEABOBS, swimming, and even learning to captain a boat.

Sessions are held Monday–Friday, 9–12:00pm for ages 9–16 and operate from July 1 to August 30.

Learn to Sail_website
PRIVATE LESSONS

Learn to sail with personalized, hands-on instruction tailored to your experience level and goals. Whether you're stepping aboard for the first time or refining advanced skills, our private lessons provide a comfortable and confidence-building environment on the water.

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COMMODORES CLUB

Take your sailing lifestyle to the next level. The Commodores Club offers exclusive access, member benefits, and a welcoming community of sailors who share a passion for adventure, learning, and time on the water. Enjoy more opportunities to sail, connect, and make the most of every season.

Two boys wearing life jackets and swim trunks jump off the back of a motorboat into a wide, sunny lake.
SAILING CHARTERS & DAY SAILS

Escape the everyday and experience the beauty of the coastline under sail. From relaxing afternoon cruises and sunset sails to private celebrations and custom excursions, our charters are designed to create unforgettable moments on the water with family and friends.

TWENTY-NINE YEARS OF SAILING IN THE HAMPTONS
Sag Harbor Sailing logo for a sailing school and charter company in Sag Harbor, NY
"We had a great day out on the water! The boat was in awesome shape and the staff were super helpful!"
Julia W
on Yelp
★★★★★
Sag Harbor Sailing logo for a sailing school and charter company in Sag Harbor, NY
"Great trip fishing with captain Bob! He was great with kids. Two hour fishing trip is just right."
Bob H
on Yelp
★★★★★
Sag Harbor Sailing logo for a sailing school and charter company in Sag Harbor, NY
"My wife, 2 boys and I hired Mark for the sunset cruise. He was great, the weather was beautiful and our evening was perfect. I highly recommend."
Billy S
on Yelp
★★★★★

I WANT TO ESCAPE FOR THE DAY!