Windward Sailing Charters

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Bay Ave
Oyster Bay, NY 11771

Windward Sailing Charters offers private sailing charters, sunset cruises, and sailing lessons in Oyster Bay, NY. Situated in the heart of Long Island's Gold Coast, Oyster Bay Harbor provides a temporary respite from bustling city life with its natural beauty, diverse wildlife, and impressive estates. Guests can sail aboard the meticulously kept Jeanneau Sun Odyssey 36i, WINDSWEPT, which features a spacious shaded cockpit and modern electronics, ensuring a memorable and enjoyable experience.

Owned and operated by USCG licensed OUPV Captain Jonathan, Windward Sailing Charters provides a personalized sailing experience with a maximum of 6 guests per charter. Whether celebrating a special occasion, interested in learning to sail, or planning a corporate team building outing, guests can customize their experience and enjoy the calm waters of Oyster Bay, which are typically protected and calm even on windy days. With a flexible cancellation policy and the option to bring your own food and beverages, Windward Sailing Charters offers a unique opportunity to explore the beauty of Long Island's historic Gold Coast.

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5.01 reviews
Photo of Elizangela D.
Elizangela D.
6/28/2023

What a great experience! All I needed to do to go on Capitan's Jonathan's exquisite Sailboat was showing up. He had everything prepared and well planned: Drinks, route, safety equipment and...

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