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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 360 listings

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
$190+/hour
Experience premier service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premier service: NYC’s longest-running private sailing charter

5.0
$395/hour
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/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
Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets
Sailing in Sag Harbor · 41 guests

Large and Luxuriously Appointed Schooner for Private Daysails, Swims and Sunsets

5.0
$1,100+/hour
Classic Yacht Charter in New York, New York
Sailing in Manhattan · 30 guests

Classic Yacht Charter in New York, New York

5.0
$1,800/hour
Private Sailing Charters - 37ft Sailboat in New York
Sailing in Manhattan · 6 guests

Private Sailing Charters - 37ft Sailboat in New York

5.0
$325/hour
38' Sailing Yacht in Toronto, Ontario
Sailing in Toronto · 8 guests

38' Sailing Yacht in Toronto, Ontario

New
$450/hour
Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/hour
41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests
Sailing in Toronto · 12 guests

41' Beneteau Oceanis Sailing Yacht in Toronto for 12 Guests

New
$45/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
Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau
Sailing in Sag Harbor · 6 guests

Private Sailing Charter – Explore the Hamptons from Sag Harbor Aboard a Beneteau

New
$230+/hour
28' Sailboat for 5 guests in Toronto
Sailing in Toronto · 5 guests

28' Sailboat for 5 guests in Toronto

New
$300/hour
A large and luxurious French Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Sailing Yacht for up to 6

New
$750+/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$108+/hour
Instant Book
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$150/hour
2hr Shared Champagne Sail
Sailing in Toronto · 12 guests

2hr Shared Champagne Sail

New
$85/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 the Adirondack Mountain Lakes
Sailing in New York · 4 guests

Sail the Adirondack Mountain Lakes

New
$160/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
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/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

Sailing Reviews in New York

  1. Tal

    Tal

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

    From the moment we stepped aboard, it was clear this yacht was something special. Impeccably maintained with every detail thoughtfully cared for, the vessel was not only stunning but also incredibly comfortable and inviting. What truly set this experience apart was our captain. An absolute gem- professional, patient, and genuinely kind. John’s calm demeanor and warm personality created an atmosphere of ease and enjoyment throughout the entire time. Whether it was navigating the waters flawlessly or ensuring everyone felt safe and cared for, this captain went above and beyond. This was more than just a ride—it was a luxury experience wrapped in beauty, serenity, and top-tier hospitality. Highly recommend for anyone looking to create lasting memories on the water. We will definitely be back❤️

  2. 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.

  3. MR

    Matthew

    Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

    We had a great time sailing out of Port Washington with Steven! Got to sail around the harbor to see some cool houses in Great Neck, the old lighthouse, and views of New York City in the distance. Steven was very communicative and a great captain for the morning! Would do again!

  4. KS

    Katherine

    Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

    Steven was an excellent host! He answered all of our questions up to the trip and met us on the dock when we got there. The boat was great and the trip was exciting, he even let us help sail! All the views were great and we loved the whole experience!

  5. JH

    John

    Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

    Four of us went out with Captain Steve for a 3 hour sunset sail. It was calm when we got on the boat. A light breeze picked up once we got underway. We sailed out of Manhasset Bay into the LI Sound. We first headed towards the Throgs Neck Bridge. When we got abreast of Kings Point and the Merchant Marine Academy, we turned around and headed back east. Steve pointed out the various islands (e.g., Hart Island) and lighthouses and coastal points (Connecticut, Larchmont, the Bronx, Whitestone and Throgs Neck Bridges, Merchant Marine Academy, Manhattan skyline in the distance, etc.) we saw, providing appropriate history and commentary along the way. He answered numerous questions. He was a most amiable host. The boat was in great shape, clean and well maintained. We recommend this experience most highly.

  6. DK

    Dmitri

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!