Sailing in Sag Harbor with Sag Harbor Sailing
Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels; minimal physical effort required
Overview
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.
23’ Pearson Ensign Rental
Sailing Rentals, up to 6 Guests
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Adventure Photos
About This Adventure
Embark on an unforgettable sailing adventure in the Hidden Hamptons! Explore the stunning shorelines of Long Island’s Twin Forks aboard a 23′ keel boat, perfect for up to six passengers. Experience the blend of luxury and natural beauty, making every moment on the water truly memorable.
Discover the Hidden Hamptons!
About
Discover the Hidden Hamptons! The shore lines of Long Island’s Twin Forks are home to some of the world’s most prestigious residences and natural beauty. Enjoy sailing aboard a 23′ keel boat with outboard engine, room for six passengers plus, if needed, one of our captains. Captains cost $300.00 for full day or $200.00 for a half day or $125 for sunset.
Adventure Tips
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.
Local Insights
Wildlife
- Seabirds like gulls and cormorants
- Local seals occasionally sunbathe on rocks
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.
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Adventure Hotspots in New York City
Frequently Asked Questions
Recommended Gear
Sunscreen
Protects your skin from UV rays while on deck during sunny days.
summer specific
Hat and sunglasses
Keeps you comfortable and shielded from bright sunlight.
summer specific
Layered clothing
Helps you stay warm in cooler weather or chillier breezes.
spring|fall|winter specific
Water bottle
Stay hydrated throughout your sailing adventure.