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!
From the operator’s live schedule on Viator, checked Oct 12.
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 91 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Oyster Bay Two Hour Sailing Experience lasts about 2 hours.
Prices start at $650 per person for this Long Island experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is 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. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a private experience: only your party takes part. Up to 15 travellers can book together.
Confirmation is sent by the operator within 24 hours of booking.
Travellers rate it 5.0 out of 5 across 2 reviews on Viator and Tripadvisor; it is run by Windward Sailing Charters.
Reviews collected by Viator and Tripadvisor
Went with five friends for a sunset sail. This is an incredible experience! Booking was easy, and we had amazing views of the local area. Capt. Jonathan went above and beyond to make sure everyone was having a great time. Can’t recommend this experience enough!
Thank you so much for taking the time to write this review and share your experience! Hope to see everyone again one day!
Phenomenal experience. Captain Jonathan kept our group informed and made sure we had a great time. 11/10 would do it again!
Thank you for taking the time to write about your experience! So happy to hear that everyone had fun! Until next time!
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Oyster Bay Two Hour Sailing Experience | 2 hours | 5.0 (2) | $650 | |
 Outrageous Oyster Bay Scavenger Hunt | 2 hours | — | $23 | View |
 Private Long Island Sound Sailing Experience | 3 hours | — | $650 | View |
 Oyster Bay Three Hour Sailing Experience | 3 hours | — | $825 | View |
 Captain Steve's Sailing Experience on Long Island | 2 hours | 5.0 (11) | $550 | View |
 Skip the Lines Reliable Comfortable and stress free Rides | 45 min–1h 15min | 5.0 (153) | $215 | View |
 Bermuda Aquarium and Crystal Caves Admission | 4 hours | 4.4 (71) | $159 | View |