Best results for Sailing in Oyster Bay, NY

Cruise Oyster Bay Harbor as the sun sets

Build team racing skills and strategy on Long Island Sound

Build your sailing skills with instructor-guided time on Oyster Bay Harbor

Step aboard CHRISTEEN to see harbor sights and learn its story

Learn the basics aboard a relaxed harbor sail led by a certified instructor

Help raise the sails or take the helm aboard a traditional tall ship

Sail into sunset aboard a traditionally rigged schooner

Learn sailing basics and take the helm on the Hudson River

Build your sailing skills with instruction tailored to your goals

Cruise NYC Harbor at sunset on the historic yacht Ventura

Private NYC sailboat cruise from Chelsea Piers, with skyline and landmark views

Private sunset sail from Chelsea Piers with skyline and Statue of Liberty views

Sail NYC on a private charter with a U.S. Coast Guard licensed captain

Plan a proposal sail with skyline views and personalized details

Private harbor sailing with sunset views of New York City landmarks

Private sailboat cinema with a film of your choice

Private harbor sailing with close-up Statue of Liberty views

Sail New York Harbor with skyline views, a private yacht, and your own captain

Private New York Harbor sailing for a romantic celebration

Sail New York Harbor aboard a historic tall ship with close Statue of Liberty views

Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening

See New York Harbor from a historic tall ship in pre-sunset light

Live jazz, harbor landmarks, and sunset views aboard a tall ship

Private New York Harbor sail with views of the Statue of Liberty