Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Map View

All listings in New York

Incredible sailboat rentals in New York, United States.

5.0

(780 Reviews)

Page 1 of 3 • 70 listings

Sailing in Manhattan · 6 guests

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

5.0

Superowner

Best of 2025

$240+/hour

Sailing in Manhattan · 6 guests

The Only 40ft Hinckley Sailboat in Manhattan

5.0

$300/hour

Instant Book

Sailing in Etobicoke · 6 guests

35ft C&C 35 Sailboat in Toronto

5.0

$179/hour

Sailing in Salisbury · 2 guests

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

5.0

$85/hour

Sailing in Sag Harbor · 6 guests

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

5.0

$750/hour

Sailing in Manhattan · 6 guests

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

5.0

Superowner

$300+/hour

Instant Book

Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9

Superowner

Best of 2025

$200+/hour

Sailing in Toronto · 6 guests

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

5.0

$89+/hour

Sailing in Norwalk · 12 guests

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

4.7

Superowner

$200/hour

Sailing in Huntington · 12 guests

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

5.0

Superowner

$150/hour

Sailing in Manhattan · 6 guests

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

5.0

$285/hour

Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.7

$475/hour

Events in Manhattan · 12 guests

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

5.0

$475/hour

Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0

$146/hour

Sailing in Manhattan · 6 guests

Sailing NYC aboard 34' Catalina

5.0

Superowner

$285/hour

Sailing in Sag Harbor · 25 guests

A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

5.0

$850/hour

Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0

$325/hour

Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0

$50/hour

Sailing in Oyster Bay · 6 guests

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

5.0

$190+/hour

Instant Book

Sailing in Manhattan · 6 guests

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

5.0

$295/hour

Sailing in Prince Edward · 12 guests

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

4.9

$322/hour

Instant Book

Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0

$268/hour

Sailing in Manhattan · 12 guests

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

5.0

$700/hour

Sailing in Port Washington · 12 guests

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

4.8

Superowner

$219/hour

Top Destinations Nearby

Sailing Reviews in New York

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!
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!
Abhishek

The Only 40ft Hinckley Sailboat in Manhattan
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.
AM
Angela

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Wonderful experience with my 2 daughters! They jammed out to their favorite music while enjoying the sights and were given a chance to steer the boat! Ian was attentive and amiable throughout the booking and sailing experience.
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!
Jonathan

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
Ian was a gracious host. Perfect trip and captain. I would highly recommend you use his sailboat!