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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 349 listings

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
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
$240+/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$275/hour
Limited Availability
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
North River Sailing - See NYC from a Classic Racing Yacht
Sailing in Manhattan · 6 guests

North River Sailing - See NYC from a Classic Racing Yacht

5.0
$315/hour
Limited Availability
Sail to the Statue of Liberty and Ellis Island aboard the 30' C&C Sailing Yacht
Sailing in Manhattan · 6 guests

Sail to the Statue of Liberty and Ellis Island aboard the 30' C&C Sailing Yacht

New
$300/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
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
Sail on a classy and fast Sailing Yacht in the Hamptons, New York
Sailing in East Hampton · 6 guests

Sail on a classy and fast Sailing Yacht in the Hamptons, New York

5.0
$340/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$161+/hour
Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$120+/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
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
Sail the Adirondack Mountain Lakes
Sailing in New York · 4 guests

Sail the Adirondack Mountain Lakes

New
$160/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
Limited Availability
ASA Practice Sailing Exercises | 30ft C&C
Tours in Manhattan · 6 guests

ASA Practice Sailing Exercises | 30ft C&C

New
$150/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
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
$1,200/hour
Limited Availability
30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline
Sailing in Bronx · 6 guests

30ft C&C 30 MK 1 Sailboat: Jersey City Harbor Sailing with Views of NYC Skyline

New
$150/hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/hour
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. PM

    Prince

    Affordable Yacht 27' Doral in Toronto

    Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.

  2. 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!

  3. 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!

  4. 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.

  5. JR

    Jai

    Sail to Fishers Island on a fast and classy 35' Sailboat

    We had a wonderful experience and found Captain Eric to be an excellent sailor and gracious host. He is extremely friendly, relaxed and a great conversationalist who has many stories to tell about the Thimble Islands and other topics. We had a large party with a two year old child and Captain Eric made us all comfortable and provided us with a perfect trip.

  6. Lauri

    Lauri

    Sail to Fishers Island on a fast and classy 35' Sailboat

    CaptIn Eric provided an amazing experience for my family. Not only did he display his professional sailing skills but he accommodated time for dining and swimming and the thrill of being under sail on a beautiful sunny and windy day. We've already shared our great experience with friends and family and hope to join them for another trip on Erics Nomade.