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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 366 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
35ft C&C 35 Sailboat in Toronto
Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0
$183/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
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
Sailing in Norwalk · 12 guests

Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

4.7
Superowner
$200/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
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
$200+/hour
Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

5.0
Superowner
$150/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
$92+/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
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
Sailing NYC aboard 34' Catalina
Sailing in Manhattan · 6 guests

Sailing NYC aboard 34' Catalina

5.0
Superowner
$285/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
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$150/hour
42' Catalina Sailing Yacht in the Hamptons
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons

5.0
$312+/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 Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$195+/hour
Instant Book
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
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
$330/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
$275/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
A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups
Sailing in Sag Harbor · 25 guests

A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

5.0
$850/hour
Sail From Port Washington, NY - $219/Hour - $37/Person
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY - $219/Hour - $37/Person

4.8
Superowner
$219/hour

Sailing Reviews in New York

  1. GE

    Glenda

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    This charter was the perfect little getaway—a mini vacation on the water that left us completely refreshed. The boat was exactly as described: clean, comfortable, and clearly cared for with pride. Every moment felt relaxing and easy, from the smooth ride to the peaceful surroundings. It was the kind of experience that makes you forget about everything else for a while—in the best way. Highly recommend for anyone needing a short but sweet escape.

  2. JC

    Julia

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

    Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!

  3. Nehal

    Nehal

    Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

    Mark’s boat is spacious. I had booked the boat during the sunset hours and the views were amazing. Mark provides detailed instructions for the pickup and is very punctual.

  4. AL

    Abby

    The Only 40ft Hinckley Sailboat in Manhattan

    Captain Andy was amazing- super accommodating and flexible. We got EPIC engagement pictures , while also having the best experience :). only amazing things to say!

  5. FS

    FRANCI

    Sailing NYC aboard 34' Catalina

    Ian provided us with a fantastic sailing experience for our wedding anniversary. It was absolutely lovely—truly beyond our expectations. His communication and instructions were clear and outstanding from start to finish. On the day of our sail, Ian even reached out to offer an earlier time slot when one became available, which we appreciated. The boat was perfect, and we had an unforgettable time on the water. Thank you, Ian, for making our special day even more memorable!

  6. Irina

    Irina

    35ft C&C 35 Sailboat in Toronto

    It was a great experience for me and my whole family. Peter made us a part of sailing experience and my husband and our teenagers gladly participated in everything that needed to be done and also enjoyed the conversation and the company of the captain. Thank you, Peter!