About This Tour
Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is meticulously maintained and equipped with modern amenities. Features include a fully shaded cockpit with an integrated swim platform, Bluetooth stereo, refrigeration, YETI soft cooler, and folding cockpit table. Private sailing charters are perfect settings for celebrating special occasions, enjoying a relaxing day on the water with family and friends, or hosting memorable client events. Those coming from NYC can take the Long Island Railroad (LIRR) from Penn Station to the Oyster Bay stop, which is steps to the marina!
What's Included
Photo Gallery

Spacious Cabin

Walkthrough Transom with Integrated Swim Platform

Shaded Cockpit with Seating for 6
Popular time slots can fill up fast.
TopTours Insights
Oyster Bay Two Hour Sailing Experience
This two-hour sailing trip aboard a private catamaran in Oyster Bay offers a relaxed way to enjoy the coastal scenery. It's ideal for couples or small groups seeking a peaceful outing on calm waters, with opportunities for swimming and enjoying the views.
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Additional Information
Meeting Point
Access to the boat is via launch service operated by Oyster Bay Marine Center. The launch ride is 2-3 minutes from the dock. Parking is free.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
✓ Free cancellation due to bad weather
Tour Operator
Windward Sailing Charters
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Trusted local operator
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Frequently Asked Questions
Common questions about Oyster Bay Two Hour Sailing Experience in Long Island
Who operates this experience?
This experience is operated by Windward Sailing Charters, a local water sports provider.
What's included?
This tour includes Pool floats, Stand up paddle board, and USCG Licensed Captain. Additional amenities and services are included. All inclusions are provided by the tour operator.
How long is this tour?
The experience lasts approximately 2 hours, giving you time to fully enjoy your chosen activity.
Can I cancel this tour?
Yes, you can cancel up to 24 hours before the scheduled departure time for a full refund. If weather conditions are unsafe, the tour may be canceled by the operator. In such cases, you'll be offered a refund or reschedule.
What should I bring?
We recommend bringing a swimsuit, towel, and sunscreen. All necessary equipment is provided by the tour operator.
Will I receive instant confirmation?
Yes, you'll receive instant confirmation when you book.
What to expect on this tour?
This water sports experience lasts approximately 2 hours and includes all necessary equipment and guidance. You'll have access to Pool floats and more.
What's the best time to do this tour?
Morning and early afternoon are typically the best times for water activities, as conditions are usually calmer and visibility is better.
Do I need to know how to swim?
Swimming ability requirements vary. Life jackets and safety equipment are provided. Please check the tour details or contact the operator if you have concerns about swimming requirements.
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