Windward Sailing Charters 

Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i. Moored in Oyster Bay Harbor, she features a large shaded cockpit with cushions and ample room for 6, a secured deck with double lifelines and USCG-approved safety gear. The boat is equipped with onboard refrigeration, a Bluetooth stereo, and an integrated swim platform.

Private charters can be customized to meet your needs. If you require a specific start time not listed, please reach out and we will do out best to accommodate. Whether you are celebrating a special occasion with family or friends, are interested in learning to sail, planning a client outing, or just looking to relax and take in the beautiful views of Oyster Bay Harbor, we will strive to create a memorable experience for your group.

You'll find the boat to be in exceptional condition with polished gelcoat and teak varnished to the highest standards. The spacious cockpit features a folding table, drink holders, and charging ports. Bottled water and ice are included in your charter, as is the use of a medium-sized Yeti soft cooler. The boat is also equipped with several inflatable floats and a standup paddleboard for use when the boat is moored or at anchor.

Captain Jonathan is a lifelong sailor and licensed U.S. Coast Guard Master Captain with decades of sailing experience. A Long Island native, Jonathan grew up sailing out of Oyster Bay Harbor.

For those traveling from New York City, the marina is a 5-minute walk from the Oyster Bay LIRR station or a 20-minute Uber ride from the Hicksville LIRR station.

Two-hour charters allow enough time to tour Oyster Bay and Cold Spring Harbor. Consider booking a 3 or 4 hour charter if you are interested in sailing deeper into Long Island Sound or if your group wants to sail to a quiet anchorage to relax and swim. Full-day charters allow enough time to sail to a destination, such as Huntington or Northport Harbor.