Windward Sailing Charters
Windward Sailing Charters
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i. Moored in Oyster Bay Harbor, she features a large shaded cockpit with cushions and ample room for 6, a secured deck with double lifelines and USCG-approved safety gear. The boat is equipped with onboard refrigeration, a Bluetooth stereo, and an integrated swim platform.
Private charters can be customized to meet your needs. If you require a specific start time not listed, please reach out and we will do out best to accommodate. Whether you are celebrating a special occasion with family or friends, are interested in learning to sail, planning a client outing, or just looking to relax and take in the beautiful views of Oyster Bay Harbor, we will strive to create a memorable experience for your group.
You'll find the boat to be in exceptional condition with polished gelcoat and teak varnished to the highest standards. The spacious cockpit features a folding table, drink holders, and charging ports. Bottled water and ice are included in your charter, as is the use of a medium-sized Yeti soft cooler. The boat is also equipped with several inflatable floats and a standup paddleboard for use when the boat is moored or at anchor.
Captain Jonathan is a lifelong sailor and licensed U.S. Coast Guard 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 enough time to tour Oyster Bay and Cold Spring Harbor. Consider booking a 3 or 4 hour charter if you are interested in sailing deeper into Long Island Sound or if your group wants to sail to a quiet anchorage to relax and swim. Full-day charters allow enough time to sail to a destination, such as Huntington or Northport Harbor.
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i. Moored in Oyster Bay Harbor, she features a large shaded cockpit with cushions and ample room for 6, a secured deck with double lifelines and USCG-approved safety gear. The boat is equipped with onboard refrigeration, a Bluetooth stereo, and an integrated swim platform.
Private charters can be customized to meet your needs. If you require a specific start time not listed, please reach out and we will do out best to accommodate. Whether you are celebrating a special occasion with family or friends, are interested in learning to sail, planning a client outing, or just looking to relax and take in the beautiful views of Oyster Bay Harbor, we will strive to create a memorable experience for your group.
You'll find the boat to be in exceptional condition with polished gelcoat and teak varnished to the highest standards. The spacious cockpit features a folding table, drink holders, and charging ports. Bottled water and ice are included in your charter, as is the use of a medium-sized Yeti soft cooler. The boat is also equipped with several inflatable floats and a standup paddleboard for use when the boat is moored or at anchor.
Captain Jonathan is a lifelong sailor and licensed U.S. Coast Guard 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 enough time to tour Oyster Bay and Cold Spring Harbor. Consider booking a 3 or 4 hour charter if you are interested in sailing deeper into Long Island Sound or if your group wants to sail to a quiet anchorage to relax and swim. Full-day charters allow enough time to sail to a destination, such as Huntington or Northport Harbor.
Trip availability and prices
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Customer reviews
Rating
All reviews (3)
From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain. His communication with us both before and during our 4-hour sunset cruise was casual, welcoming and thorough- and helped us enjoy every step along the way. "Windswept" was comfortable, capable and beautifully maintained- making for a relaxing, yet engaging sailing experience. Highly recommend!
highly recommend this experience with Johnathon
Jonathon welcomed my friends & I aboard as if we were family! He went above & beyond to make us comfortable in his space. He was very knowledgeable in sailing as my husband loves to learn & chat about it all. The boat was the perfect size for the 5 of us with plenty of room. The bathroom was so large for a sail boat! Getting to the sailboat was so easy & quick. We will definitely be looking to book with Jonathon again.
Thanks so much for taking the time to write a review! I’m so happy to hear that everyone had a great experience! Hope to see everyone again one day!
FAQs about Windward Sailing Charters
What are the trip rates for Windward Sailing Charters?
- US $525 per group, additional US $50 per person after 4 guests - 2 Hour Private Sailing Charter (2 hours)
- US $525 per group, additional US $50 per person after 4 guests - 2 Hour Private Sailing Charter - 10:00 AM (2 hours)
- US $525 per group, additional US $50 per person after 4 guests - 2 Hour Private Sailing Charter - 2:00 PM (2 hours)
- US $525 per group, additional US $50 per person after 4 guests - 2 Hour Private Sailing Charter - 4:00 PM (2 hours)
- US $525 per group, additional US $50 per person after 4 guests - 2 Hour Sunset Charter (2 hours)
- US $675 per group, additional US $75 per person after 4 guests - 3 Hour Private Sailing Charter (3 hours)
- US $675 per group, additional US $75 per person after 4 guests - 3 Hour Private Sailing Charter - 3:00 PM (3 hours)
- US $675 per group, additional US $75 per person after 4 guests - 3 Hour Private Sailing Charter - 9:00 AM (3 hours)
- US $675 per group, additional US $75 per person after 4 guests - 3 Hour Sunset Charter (3 hours)
- US $800 per group, additional US $100 per person after 4 guests - 4 Hour Private Sailing Charter (4 hours)
- US $800 per group, additional US $100 per person after 4 guests - 4 Hour Private Sailing Charter - 2:00 PM (4 hours)
- US $800 per group, additional US $100 per person after 4 guests - 4 Hour Sunset Charter (4 hours)
- US $1,475 per group, additional US $100 per person after 4 guests - 8 Hour Private Sailing Charter (8 hours)
- US $1,475 per group, additional US $100 per person after 4 guests - 8 Hour Private Sailing Charter - 12:00 PM (8 hours)
Which amenities are available onboard with Windward Sailing Charters?
- GPS
- VHF Radio
- Radar
- Chart Plotter
- Depth Finder
- Autopilot
- Anchor
- Dinghy
- Wheel Steering
- Life Jackets
- Bimini
- Kitchen
- Shower
- Bathing Platform
- Audio System
- Inside Speakers
- Outside Speakers
- Refrigerator
- Ice Box
- Grill
- Galley Stove and Oven
- Rod Holders
What add-ons can be available with Windward Sailing Charters?
- Paddleboard
- Drinks
Which kinds of activities does Windward Sailing Charters offer?
- Boat & Yacht Tours
- Sailing, Catamaran & Gulet Tours
- Sunset Dinner Cruises
- Booze Cruises
- Paddleboard
- Birthday Celebrations
- Bachelorette & Bachelor Parties
- Proposal & Engagement Trips
- Corporate & Group Events
Your operator
Capt. Jonathan Puleio helms his beautifully maintained 2012 Jeanneau Sun Odyssey 36i in Oyster Bay Harbor, offering memorable sailing charters, harbor tours, and sunset cruises. With a passion for the sea and decades of experience, he ensures every voyage is both relaxing and unforgettable. Whether you're seeking to experience the thrill of sailing or the tranquility of the bay, Capt. Jonathan promises to deliver an exceptional day on the water.
Capt. Jonathan Puleio helms his beautifully maintained 2012 Jeanneau Sun Odyssey 36i in Oyster Bay Harbor, offering memorable sailing charters, harbor tours, and sunset cruises. With a passion for the sea and decades of experience, he ensures every voyage is both relaxing and unforgettable. Whether you're seeking to experience the thrill of sailing or the tranquility of the bay, Capt. Jonathan promises to deliver an exceptional day on the water.
What the boat is like
Which kind of activities are offered
Which amenities are available onboard
What's included in the trip price
What’s allowed on the boat
What additional terms you should be aware of
Security deposit is not required
A refundable deposit is not required by the charter operator.
Fuel is included
Fuel is included in the price of the rental.
How cancellations work
Free cancellation up to 7 days prior to trip
You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
How you can pay
Reserve with a 10% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 10% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
PayPal
Bank transfer
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