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    Port Sailing School

    3.3 (7 reviews)
    Closed 9:00 am - 5:00 pm

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    4 years ago

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    3 years ago

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    7 years ago

    I wish someone had warned me before I signed up for their Caribbean sailing trip last year - it was a total disaster.

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    6 years ago

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    Windward Sailing Charters - Oyster Bay is known for its breathtaking sunsets.

    Windward Sailing Charters

    (1 review)

    What a great experience! All I needed to do to go on Capitan's Jonathan's exquisite Sailboat was…read moreshowing up. He had everything prepared and well planned: Drinks, route, safety equipment and amenities. The weather was perfect as it was the beginning of June. The boat is a beaty, and I was really impressed about how detailed oriented his captain is about keeping it looking and running so fine! Whether you refer to yourself as a day Sailer, sailboat rider, a weekender sailboat, or pocket cruisers, or just an immature boat lover like me - looking for some time in the water, there's no better way to enjoy the thrills of coastal sailing and wind than on this beautiful sailboat. Hope you enjoy it as much as I did!

    From the owner: Lifelong sailor and licensed USCG captain offering private sunset charters, excursions and sailing…read morelessons in Oyster Bay, NY. Private charters can accommodate up to 6 guests. WINDSWEPT is a beautifully kept 36 ft Jeanneau Sun Odyssey featuring a spacious shaded cockpit perfect for relaxing and taking in the spectacular views of Oyster Bay Harbor and Long Island Sound. She is professionally maintained and equipped with modern electronics and USCG approved safety gear. Private charters are highly customizable. Whether you are celebrating a special occasion, interested in learning to sail, or planning a client outing, your time aboard WINDSWEPT will be both memorable and enjoyable. Below is a list of the different types of charters we offer: Sunset Cruises Sail and Swim Charters Sightseeing Harbor Tours Sailing Lessons Celebrate a Special Occasion (Wedding, Anniversary, Proposal, Birthday, etc.) Corporate Events (Client Entertainment or Team Building Exercises) Destination Sails Dock & Dine Photoshoots Contact us today to learn more!

    Hudson River Sloop Clearwater

    Hudson River Sloop Clearwater

    (6 reviews)

    We went on a sail aboard the Clearwater and had a lovely time. The boat was conveniently docked by…read morethe Boat Basin on the upper west side. It's an all wood vessel designed after the old sailing sloops. And I must say it's a very good-looking vessel. The crew, which was made up of almost all volunteers, were great and very personable. As part of the trip, we all got to help hoist the sail which was quite the experience. It actually takes a lot of work and people to hoist this massive sail. We sailed in the evening and got to watch the sun set over the city. We were lucky that there was enough wind to get us moving but not too windy that it made the sail rough. We had a such a great time and wished that the sail was longer!

    Went with friends. It was a wet and slightly windy day. I was expecting to actually do some sailing…read moredown the Hudson. But to my disappointment. We just pretty much went in circles. There are no restrooms on boat or in the parking area of the park. They have an outhouse if you really need to go. Is down the stairs in a dark closet like space. So if your thinking of trying this makes sure your bladder is empty before getting on. The staff are very friendly and respectful. They can answer all your questions. It was a fun trip. Ring your own snacks they don't sell anything on the boat. I am glad I got to experience the ride on a sailing boat. But for me one and done works. You can help raise the sails if you want to.

    Port Sailing School - boatcharters - Updated September 2026

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