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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 355 listings

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
Instant Book
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Instant Book
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Limited Availability
 Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0
Superowner
Best of 2026
$240+/hour
Caribbean Vibez on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez on a Brooklyn Sailboat

5.0
Superowner
$191/hour
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$148/hour
Limited Availability
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
$475/hour
Limited Availability
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$300/hour
Luxury 49ft Sailing Yacht Charter in NY Harbor - US Coast Guard Inspected
Sailing in Manhattan · 12 guests

Luxury 49ft Sailing Yacht Charter in NY Harbor - US Coast Guard Inspected

5.0
$750/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$327/hour
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/hour
Discover Sailing 3hr Introductory Sail
Sailing in Toronto · 4 guests

Discover Sailing 3hr Introductory Sail

4.5
$69/hour
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/hour
Experience premier service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premier service: NYC’s longest-running private sailing charter

5.0
$395/hour
Chaparral 256 Family Cabin Cruiser
Powerboats in Jersey City · 9 guests

Chaparral 256 Family Cabin Cruiser

5.0
$275/hour

Sailing Reviews in New York

  1. RR

    Roberto

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian was amazing, very friendly and caring. Can’t wait to do it again Thanks

  2. Irene

    Irene

    Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

    Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

  3. LP

    Lolly

    Manhattan Luxury Sailboat - 40' Hinckley Sailboat

    I highly recommend chartering Captain Andy's sail boat! Everything in the listing was exactly as described and his boat was perfect for a day on the water. He answered all of our (admittedly dumb) questions about NYC and was super friendly and took plenty of photos of us when asked. I have no complaints and would definitely charter Captain Andy's boat again!

  4. LX

    Linda

    Manhattan Luxury Sailboat - 40' Hinckley Sailboat

    My group and I had an incredible experience with Captain Andy. He was warm, accommodating, and an excellent captain throughout the entire trip. He truly made the day unforgettable for all of us, and we can’t wait to set sail with him again. The sailboat, Nanette Marie, was stunning so comfortable and perfect for capturing beautiful photos.

  5. Abhishek

    Abhishek

    Manhattan Luxury Sailboat - 40' Hinckley Sailboat

    Captain Andy is one of the best hosts and extremely skilled at what he does. I was planning a proposal for my girlfriend and he went above in beyond in helping us out. He gets back quickly regarding any queries and makes sure you have a memorable experience. I have nothing but good this to say about our experience. Definitely recommend Captain Andy if you are looking for a good time on a sail boat.

  6. AN

    Afisha

    Manhattan Luxury Sailboat - 40' Hinckley Sailboat

    Wow! What a magical way to celebrate my birthday!! From the moment I inquired about booking with Captain Andy, he greeted me with such warmth and enthusiasm. On the day of, he was so welcoming towards my family and I, handling us with such patience and care, ensuring our safety and comfort. And, let’s not forget the level of skill he harnessed as we sailed the Hudson! We took on a few waves; there was a particularly big one that quickly became the highlight of our trip. Some members of my family have had bad experiences in water, but I was delighted to share and witness their excitement around facing it. Trusting in Captain Andy’s years of sailing experience we were all free to embrace a little splash. My little sister’s reaction was especially precious, as it was her first time being aboard a boat. “More waves! More!” Haha! Thank You, Captain Andy for such a memorable sail experience. This definitely won’t be my last time booking. To those of you reading, what are you waiting for?! Book him!!