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 ample room for 6, a secured deck with double lifelines and USCG-approved safety gear. The boat is equipped with onboard refrigeration, a new Bluetooth stereo and an integrated swim platform.

Private charters can be customized to meet your needs. Whether you are celebrating a special occasion with family or friends, 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 use of a medium sized Yeti soft cooler. The boat is also equipped with several inflatable floats and a standup paddle board for use when the boat is moored or at anchor.

Captain Jonathan is a lifelong sailor and U.S. Coast Guard licensed charter boat 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 steps away from the Oyster Bay LIRR station or a 20-minute Uber ride from the Hicksville LIRR station.

Two-hour charters allow just enough time to sail to the mouth of Oyster Bay Harbor and back. Consider booking a longer charter if you are interested in sailing deeper into Long Island Sound or if you want to leave time for swimming at the mooring. Full Day charters allow enough time to sail to a destination, such as Huntington or Northport Harbor. Your group can venture into town to indulge in a cocktail or enjoy a delicious meal at one of the many restaurants.