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Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

With Captain

100% refund within 5 days of your trip
  • Looks Good

    This date is available.

Relaxed, luxurious-feeling sails along Long Island’s Gold Coast, with calm, scenic views that leave guests refreshed and creating easy, lasting memories.
Well‑kept sailboat with a shaded, cushioned cockpit and spacious deck, consistently praised for being spotless, comfortable, and thoughtfully maintained.
Guests highlight a calm, kind, and personable captain with strong local knowledge who creates a welcoming atmosphere and keeps everyone at ease throughout.
Renters say this listing is great for:
Family TimeSightseeingLuxury ExperienceRelaxation
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AI Overview

Owner's Description

Sail Long Island's Gold Coast aboard a beautifully maintained 36' Jeanneau sailboat! Moored in Oyster Bay Harbor, WINDSWEPT features a large shaded cockpit with cushions and ample room for 6, a spacious deck, and US Coast Guard approved safety gear. The boat is equipped with onboard refrigeration, a powerful Bluetooth stereo and an integrated swim platform. Private sailing charters can accommodate a maximum of 6 guests and 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, a photoshoot, or just looking to relax and take in the beautiful views of Oyster Bay harbor, your time aboard WINDSWEPT will be memorable and enjoyable. Charter pricing is below. Per person pricing is calculated based on 6 guests and includes a licensed Captain but does not include the site's booking fee of ~16%. - 2-hour charter: $600 ($100/person) - 3-hour charter: $825 ($138/person) - Half Day Charter: $1000 ($167/person) - Full Day Charter: $1800 ($300/person) WINDSWEPT's cockpit features a folding table, cushions, 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 two standup paddleboards for use when the boat is moored or at anchor. Captain Jonathan is a lifelong sailor and U.S. Coast Guard licensed Master 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 a 5-minute walk 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 3 or 4-hour 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 meal at one of the many restaurants. Below are some additional activities to consider before or after your charter, many of which are in walking distance from the marina. Please check hours as several attractions are only available on certain days of the week. Sagamore Hill National Historic Site (Teddy Roosevelt's former home) Raynham Hall Museum John P Humes Japanese Stroll Garden Oyster Bay Railroad Museum Muttontown Preserve Theodore Roosevelt Nature Sanctuary Cooper Bluff Waterfront Bar Oyster Bay Brewing Company Wild Honey (restaurant) 2 Spring (restaurant) Teddy's Bully Bar (restaurant)

Jonathan

Jonathan

16 total bookings
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (10 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  2. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  3. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  4. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  5. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  6. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  7. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  8. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
  9. Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
9 photos have been added by reviewers who booked this listing.
  1. KN

    Karinne

    Jonathan is a gentleman, we had a wonderful time !

  2. KG

    KJ

    Jonathan is very knowledgeable of the area and a great captain. Will definitely book with him again!

  3. jj

    joy

    stellar experience overall, great memories with my family and learned a little history about oyster Bay.

  4. RS

    Robert

    Jonathan is a very personable and friendly guy. Would definitely book with him again.

  5. Tal
    Tal

    From the moment we stepped aboard, it was clear this yacht was something special. Impeccably maintained with every detail thoughtfully cared for, the vessel was not only stunning but also incredibly comfortable and inviting. What truly set this experience apart was our captain. An absolute gem- professional, patient, and genuinely kind. John’s calm demeanor and warm personality created an atmosphere of ease and enjoyment throughout the entire time. Whether it was navigating the waters flawlessly or ensuring everyone felt safe and cared for, this captain went above and beyond. This was more than just a ride—it was a luxury experience wrapped in beauty, serenity, and top-tier hospitality. Highly recommend for anyone looking to create lasting memories on the water. We will definitely be back❤️

Jonathan

Jonathan

16 total bookings

Jonathan is a lifelong sailor and licensed OUVP charter boat captain with decades of sailing experience. A Long Island native, Jonathan grew up sailing out of Oyster Bay Harbor.

Features & Details

  • Jeanneau
  • Sun Odyssey 36i
  • Capacity: 6 people max

Safety Equipment

Anchor & Rode
Bilge Pumps
Carbon Monoxide Detectors
Emergency Steering
Fire Extinguishers
First Aid Kit
Flares
Life Jackets (1)
Lifebuoys
Medical Supplies
Navigation Lights
Navigation Equipment
PFDs (6)
Radar Reflectors
Sound Signals
Tool Kit
VHF Radio

Operating Equipment

AIS
Autopilot
Dinghy/Tender
GPS ChartPlotter
Inverter
Depth Sounder

Guest Amenities

BBQ
Berths (1)
Cabins (1)
Cooler
Fridge
Kitchen Utensils
Oven
Pillows & Blankets
Shower
Sink
Stove
Sun Protection
Toilets (1)
Towels
Washrooms Onboard

Leisure & Entertainment Equipment

Bluetooth
Floats
Sound System
Indoor dinning Area
Indoor Lounge Area
Outdoor Dinning Area
Outdoor Lounge Area

Accessories

Inflatables (1)
Rods
Tackle
Paddleboards

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

5 Bay Avenue
Oyster Bay, New York, 11771
United States
Departure Location

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 5 days before your trip.

Additional Terms & Information

- Children under 12 must wear life jackets per USCG regulations; life jackets are provided - Maximum of 6 guests per USCG regulations - Only non-marking soles allowed (no shoes preferred) - Hard coolers are not permitted (they can damage the deck) - Soft coolers are permitted; a medium size soft cooler is available for use during your charter - Guests must be physically able to step on and off the launch boat - Cancellation due to inclement weather is permitted if chance of rain is >40% during the scheduled time of your charter, sustained winds are greater than 25 knots, or there is a threat of lightning

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