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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 248 listings

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
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
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
$160/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
$156+/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
110ft Luxury Yacht Private Charter in NYC | 6-Course Dinner and Live Music
Tours in Manhattan · 120 guests

110ft Luxury Yacht Private Charter in NYC | 6-Course Dinner and Live Music

New
$3,000/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
$750/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour
 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 2026
Snoozed - Active 02 Oct 2026
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
Snoozed - Active 23 Sep 2026
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
Snoozed - Active 28 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

Sailing Reviews in New York

  1. MC

    Marco

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is a great captain. You can truly see he loves to sail. The best way to be lead on an adventure is by someone who is passionate. He has a lot of knowledge regarding the cityscapes the surround our rivers here in NYC. I have seen the city from the sky during heli rides and can say sailing was so much better. Will definitely bring more visiting family and friends to sail with him.

  2. RA

    Rosette

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Captain Ian was professional, knowledgeable, and created a relaxed, welcoming atmosphere from the moment we stepped aboard. The boat was beautiful, the views of the Manhattan skyline were incredible, and the entire experience felt both peaceful and memorable. Captain Ian made sure everyone was comfortable while sharing interesting insights along the way. If you’re looking for a private sailing experience on the Hudson that’s both scenic and personal, I highly recommend booking with Captain Ian. We can’t wait to sail again!

  3. AB

    Alan

    Sail in downtown Toronto

    Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.

  4. KD

    Katherine

    Sail in downtown Toronto

    We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!

  5. GK

    Galina

    Sail in downtown Toronto

    Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!

  6. PS

    Pierangela

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We had an amazing time on the boat! Ian was incredibly attentive, friendly, and made sure we were comfortable throughout the entire trip. The boat was beautiful, very clean, and well maintained. The cruise itself was absolutely incredible relaxing, scenic, and a perfect experience from start to finish. We would definitely recommend this tour to anyone looking for a memorable day on the water. Thank you, Ian!