Starting at $575 • For Groups of up to 4 People
Unlock your sailing potential with personalized private lessons in Sag Harbor, NY. Tailored sessions for up to four offer expert instruction on Long Island’s iconic waters.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
2–3 hours
Fitness Level
Participants should have average fitness to manage movement on a small sailboat and handle basic sailing moves.
Wildlife
History
Sag Harbor was once a major whaling port in the 19th century, contributing significantly to Long Island’s maritime heritage.
Conservation
Local operators emphasize sustainable boating practices to preserve water quality and protect marine ecosystems in Peconic Bay.
Sag Harbor Sailing
Starting at $575 • For Groups of up to 4 People
Sag Harbor Sailing is a small, Sag Harbor, New York–based sailing company specializing in rentals, instruction, and youth programs focused on safe, skillful small-boat sailing. Founded by experienced captains and certified instructors, Sag Harbor Sailing operates a fleet centered on a 23′ Pearson Ensign keelboat used for rentals, American Sailing Association (ASA) certification courses, private lessons, and youth summer sessions.
The company offers a two-day ASA 101 Beginner Keelboat Course providing hands-on instruction in basic seamanship, points of sail, sail trim, tacking, jibing, docking, and safety procedures. Rentals of the 23′ Pearson Ensign accommodate up to six passengers for coastal exploring around the Twin Forks and Long Island shorelines. Private lessons run two- or three-hour sessions for up to four students and deliver personalized coaching tailored to skill level and goals. The youth summer program limits enrollment to twelve students per session, combines sailing practice with water sports and fishing, and is led by licensed captains and certified instructors. Safety equipment, life jackets, and briefings are standard for every activity. Reservations, scheduling, and course details are managed through the business’s booking system and staff. Sag Harbor Sailing emphasizes practical, hands-on learning, local knowledge of Sag Harbor waters, and adherence to American Sailing Association standards where applicable. Photographs, trip summaries, and clear booking policies help prospective guests choose the right experience. Reviews and third-party listings feature the business for its focused small-group instruction and accessible keelboat rentals. Booking information, rates, and seasonal availability are listed on the business website online directly.
Boat Size
23′ Pearson Ensign
Holds up to six passengers
ASA Course
ASA 101 Beginner Keelboat
Two-day certification course
Youth Program
12 per session
Limited small-group summer sessions
Private Lessons
2- or 3-hour
Private coaching for up to four
Reserve a 23′ Pearson Ensign rental, enroll in ASA 101, book private lessons, or register for the youth summer program — check availability and rates online.
Arrive early to prep
Show up 15 minutes before your lesson to get briefed and familiarize yourself with the boat setup.
Dress for the weather
Wear layers and bring a waterproof jacket to stay comfortable in changing coastal conditions.
Sun protection is crucial
Apply sunscreen and bring a hat and sunglasses to protect yourself from the sun's glare on the water.
Stay hydrated
Bring a water bottle to keep hydrated during your time on the water, especially on warmer days.
Non-slip boat shoes
Provides secure footing on a wet deck for safety and stability.
Waterproof jacket
Protects against spring breezes and unexpected rain during lessons.
spring
Sunglasses with UV protection
Reduces glare from the water and protects eyes from UV rays.
summer
Layered clothing
Allows you to adapt to fluctuating temperatures in coastal fall weather.
fall