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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 360 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
$345/hour
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
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
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
#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
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/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
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
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
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
$325/hour
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$271/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
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
Jeanneau 39i Julia Sailing Yacht in NY Harbor
Sailing in Manhattan · 6 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$400/hour

Sailing Reviews in New York

  1. NG

    Nicole

    Sailing NYC aboard 34' Catalina

    We had such a great evening sailing around NYC! Andrew was a wonderful host and captain and even went out of his way to help one of our group struggling with motion sickness. We enjoyed the route and putting up the sail in the harbor! Overall, it was an awesome experience, and I would definitely recommend booking for a fun and memorable experience!

  2. Maria

    Maria

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We had an absolutely perfect experience with our captain! From start to finish, everything was seamless—professional, friendly, and so attentive. The boat was in excellent condition, and the captain made us feel safe and comfortable the entire trip. His knowledge of the area and smooth handling of the boat made the day unforgettable. We couldn’t have asked for a better experience. Highly recommend!

  3. 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!

  4. 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!

  5. MS

    Megan

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We celebrated our 10th anniversary on Faith and couldn’t be happier. Captain Ian personalized the journey for us and guided us along the way. He was exuberant, caring, and checked in with us to make sure we were having a great time. He asked if we wanted to learn sailing and taught us a few things, which was so cool and unexpected. We are excited to sail again to learn more and see the beautiful sites NYC has offer!

  6. AS

    Andie

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian and Kim were fantastic hosts, captain and first mate! We used Ian’s vessel for a music video shoot, and not only were they helpful and accommodating, but happy to have us aboard and a part of our production. I highly recommend booking with Ian for a similar situation or if you just wanted a fun outing with some good friends!