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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 247 listings

Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,900/hour
Limited Availability
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/hour
Limited Availability
Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
Sailing in Manhattan · 6 guests

Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

5.0
$224+/hour
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
Sailing in Sag Harbor · 41 guests

Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

5.0
$1,100+/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$158+/hour
Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Learn To Sail 23' Pearson With Instructor In Sag Harbor, New York

New
$249/hour
ASA Practice Sailing Exercises | 30ft C&C
Tours in Manhattan · 6 guests

ASA Practice Sailing Exercises | 30ft C&C

New
$250/hour
A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6

New
$1,000+/hour
Private Sail Charter of NYC Skyline and Statue of Liberty
Sailing in Manhattan · 6 guests

Private Sail Charter of NYC Skyline and Statue of Liberty

New
$250+/hour
SAIL Historic Southern Lake Champlain on 30ft Catalina Sailboat
Sailing in New York · 6 guests

SAIL Historic Southern Lake Champlain on 30ft Catalina Sailboat

New
$150/hour
Day Sail Statue of Liberty, Ellis Island and Wall Street
Sailing in Manhattan · 6 guests

Day Sail Statue of Liberty, Ellis Island and Wall Street

New
$250/hour
Sail the Adirondack Mountain Lakes
Sailing in New York · 4 guests

Sail the Adirondack Mountain Lakes

New
$160/hour
40ft Pirate Ship Themed Catamaran in Dobbs Ferry
Sailing in New York · 12 guests

40ft Pirate Ship Themed Catamaran in Dobbs Ferry

New
$289/hour
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Greenport · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
27  feet of fun in the summer sun, under sail!
Sailing in Brooklyn · 6 guests

27 feet of fun in the summer sun, under sail!

New
$150/hour
Sunset Cruise Lady Liberty, Wall Street and the Brooklyn Bridge
Sailing in Manhattan · 6 guests

Sunset Cruise Lady Liberty, Wall Street and the Brooklyn Bridge

New
$250/hour
Sail the glamorous Hamptons in a 58ft Catana luxury catamaran
Sailing in Sag Harbor · 12 guests

Sail the glamorous Hamptons in a 58ft Catana luxury catamaran

New
$900/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/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
Snoozed - Active 17 Sep 2026
Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.
Sailing in Brooklyn · 6 guests

Sail New York's historic waterways aboard Water Music, a classic 40 foot yacht.

5.0
Snoozed - Active 02 Jan 2027
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
Snoozed - Active 17 Sep 2026

Sailing Reviews in New York

  1. CL

    Cathy

    Private Sail from Brooklyn Bridge Park

    Ian was a great captain. Very fun to sail with and he made us feel very comfortable. Celebrated my 30th and couldn’t recommend this experience, esp with Ian, more.

  2. CS

    Cait

    Private Sail from Brooklyn Bridge Park

    We had the best time on the boat trip. Michael was a great captain who was helpful and friendly. I would highly recommend this boat tour.

  3. NG

    Nicole

    Private Sail from Brooklyn Bridge Park

    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!

  4. ME

    Malky

    Private Sail from Brooklyn Bridge Park

    Sailing with this boat was a truly beautiful and magical experience!! It was comfortable and looked fresh too. We had a wonderful captain and he was very experienced and smooth! Ian was very responsive and accommodated us with our specific timing at sunset. My husband and I really enjoyed our night on the water!

  5. FS

    FRANCI

    Private Sail from Brooklyn Bridge Park

    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. VL

    Van

    Private Sail from Brooklyn Bridge Park

    It's a bit windy but we all enjoyed the view and how friendly and professional Andrew is. He was very kind in helping my friend who has sea sickness. I had a wonderful birthday today on the boat even though it was cold. Also, they kindly waited for me to arrive due to unexpected traffic jam.