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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

Luffing the Jib

SAILING BOAT RENTALS

23′ Pearson Ensign 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.

3-Hours $475

Sailing Classes & Lessons
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 personalized attention and effective learning.

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

2-Hours $325 and 3-Hours $445

Sag Harbor Sailing

SUMMER YOUTH PROGRAM

The Ultimate Summer for Your Child
Offered throughout the summer, our week-long program features a wide range of activities on the water including sailing, wake boarding, tubing, water skiing, learning to captain a boat, fishing, clamming, paddle boarding, SEABOBS, swimming and more.

Sessions are held Monday–Friday for ages 9–15 and operate from June 10 to August 30. Sign up for multiple weeks or just for the day.

TWENTY YEARS OF SAILING IN THE HAMPTONS

"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

"We rented a sailboat on Sat. Beautiful day. Captain Mark was great and let us be hands-on as possible sailing the 23 ' Pearson Ensign. Would recommend highly!"

– shelleyrey on Tripadvisor

"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."

– Bill S. on Yelp

"Great trip fishing with captain Bob! He was great with kids. Two hour fishing trip is just right."

– Bob H. on Yelp