SAG HARBOR SAILING

Rentals, Lessons, Charters and Summer Youth Programs

View Our Fleet

EXPLORE SAILING LESSONS, RENTALS AND YOUTH PROGRAMS

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

Sag-Harbor-Sailing-Rentals_KEY_luffing-the-jib
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.

Young-woman-on-sailboat_KEY-1
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.

kids-jumping-off-boat_8_6
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.

TWENTY YEARS OF SAILING IN THE HAMPTONS
SHS_DrkBlue_Horizon_web - Copy
"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
★★★★★
SHS_DrkBlue_Horizon_web - Copy
"Great trip fishing with captain Bob! He was great with kids. Two hour fishing trip is just right."
Bob H
on Yelp
★★★★★
SHS_DrkBlue_Horizon_web - Copy
"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!