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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 364 listings

 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 2025
$240+/hour
The Only 40ft Hinckley Sailboat in Manhattan
Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan

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

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
Best of 2025
$225+/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/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
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
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Sailing in Manhattan · 6 guests

Woman-owned luxury with transparent pricing - read our 5-star reviews!

5.0
$285/hour
27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$91+/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
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$148/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
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
Sailing NYC aboard 34' Catalina
Sailing in Manhattan · 6 guests

Sailing NYC aboard 34' Catalina

5.0
Superowner
$285/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
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$295/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
$326/hour
Instant Book
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
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$272/hour
Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic Mahogany Trimaran

5.0
$750+/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

Sailing Reviews in New York

  1. NT

    Nick

    Sail From Northport or Huntington, NY

    Mark is a wonderful captain and person all around. He is very communicative and informative both before and while we were on his sailboat. We had the best time sailing from Huntington to Northport. He sang a Happy Birthday to our Mom and brought out his guitar! Thanks so much, Captain Mark!

  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

    The Only 40ft Hinckley Sailboat in Manhattan

    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. Tarik

    Tarik

    Cruising Monohull Rental in Kingston

    Great sail. Our captain Rob was very knowledgeable and easy to talk to. He let us help with some of the sailing and then we sat at the front of the boat and enjoy the view. It was a perfect day weather wise. Had a great time overall.

  5. LE

    Lara

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

    My girlfriends and I had the best time celebrating a bachelorette party with Captain Brian and his beautiful boat! From the very start Brian had quick communication and was helpful answering our questions. The actual boat was so nice, with a rustic charm. It comfortably fit all 10 girls. Brian made the day extra special - he’s so kind and fun. Would definitely recommend to this others and even hope to do another trip again!

  6. EC

    Emily

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

    Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!