Set sail aboard a 23’ Pearson Ensign with Sag Harbor Sailing and discover the scenic shoreline of Long Island’s South Fork. Perfect for casual cruises or sailing lessons, this trip offers a peaceful escape on the water. Read on to find out why this adventure is a top choice for visitors seeking a maritime experience with a personal touch.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels; minimal physical effort required
Wildlife
History
Sag Harbor has a storied maritime past, once serving as a major whaling port in the 19th century, which laid the foundation for its sailing traditions today.
Conservation
Sag Harbor Sailing emphasizes responsible boating practices, helping preserve the delicate coastal ecosystems and ensure the waters remain pristine.
Sag Harbor Sailing
Set sail aboard a 23’ Pearson Ensign with Sag Harbor Sailing and discover the scenic shoreline of Long Island’s South Fork. Perfect for casual cruises or sailing lessons, this trip offers a peaceful escape on the water. Read on to find out why this adventure is a top choice for visitors seeking a maritime experience with a personal touch.
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.
Check the weather forecast before heading out
Wind and water conditions can change quickly, so plan accordingly for a safe and enjoyable trip.
Bring sun protection and water
Even on cloudy days, the sun’s reflection on the water can be intense; stay hydrated and protected.
Dress in layers
Temperatures can vary, especially on the water, so layering ensures comfort throughout the trip.
Learn local maritime history
Sag Harbor has a rich boat-building and sailing history that adds context to your experience.
Sunscreen
Protects your skin from UV rays while on deck during sunny days.
summer
Hat and sunglasses
Keeps you comfortable and shielded from bright sunlight.
summer
Layered clothing
Helps you stay warm in cooler weather or chillier breezes.
spring|fall|winter
Water bottle
Stay hydrated throughout your sailing adventure.