Windward Sailing Charters 

5.0
/5
(1 review)
 5 Bay Avenue, Oyster Bay, NY 11771, United States

Windward Sailing Charters 

5.0
/5
(1 review)
map-thumbnail
5 Bay Avenue
Oyster Bay, NY, United States

Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36 I. Moored in Oyster Bay Harbor, she features a large shaded cockpit with ample room for 6, a secured deck with double lifelines and USCG-approved safety gear. The boat is equipped with onboard refrigeration, a new Bluetooth stereo, and an integrated swim platform.

Private charters can be customized to meet your needs. 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 U.S. Coast Guard licensed charter boat 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 steps away 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 longer 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 delicious meal at one of the many restaurants.

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Customer reviews

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Rating summary

5.0/5
out of 5 stars from 1 review
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photo by reviewers

There are no review photos
for this charter yet!

Customer rating

1
0
0
0
0

Customers claimed

Good experience

100%

Appropriate for children

0%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

100%

Showing 1 - 1 of 1 review
Showing: 1 of 1 review
Amanda J.
Amanda J.
5.0/5

Aug 2, 2025

3 Hour Private Sailing Charter

Amazing!

VERIFIED

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.

Jonathon welcomed my friends & I aboard as if we were family! He went above & beyond to make us comfortable in his space. He was...  

Captain replied
 Amanda J. recommends Windward Sailing Charters
 Amanda J. recommends Windward Sailing Charters
undefined (The Captain)
Replied on August 4, 2025
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!

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
March 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour Private Sailing Charter
FREE Cancellation 3 days notice
2 Hour Trip, starts at 12:00 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $525 
2 Hour Sunset Charter
FREE Cancellation 3 days notice
2 Hour Trip, starts at 6:30 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $525 
3 Hour Private Sailing Charter
FREE Cancellation 3 days notice
3 Hour Trip, starts at 12:00 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $675 
3 Hour Sunset Charter
FREE Cancellation 3 days notice
3 Hour Trip, starts at 6:00 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $675 
4 Hour Private Sailing Charter
FREE Cancellation 3 days notice
4 Hour Trip, starts at 12:00 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $795 
4 Hour Sunset Charter
FREE Cancellation 3 days notice
4 Hour Trip, starts at 5:00 PM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $795 
8 Hour Private Sailing Charter
FREE Cancellation 3 days notice
8 Hour Trip, starts at 10:00 AM
Seasonal trip May 1 - Nov 1
Price for up to 6 people
US $1,495 
There is 1 person looking at this listing.

Customer reviews

Loading...

Rating summary

5.0/5
out of 5 stars from 1 review
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photo by reviewers

There are no review photos
for this charter yet!

Customer rating

1
0
0
0
0

Customers claimed

Good experience

100%

Appropriate for children

0%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

100%

Showing 1 - 1 of 1 review
Showing: 1 of 1 review
Amanda J.
Amanda J.
5.0/5

Experience:

5.0/5

Equipment

5.0/5

Crew

5.0/5

Overall

Amazing!

VERIFIED

3 Hour Private Sailing Charter on August 2, 2025

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.

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.  

 Amanda J. recommends Windward Sailing Charters
undefined (The Captain)
Replied on August 4, 2025
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

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What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Jeanneau
Boat Model
Sun Odyssey 36i
Year built
2012
Boat length
36 ft
Capacity
6 persons
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