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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 2 of 247 listings

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

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/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
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
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
Limited Availability
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
$197+/hour
Affordable Yacht 27' Doral in Toronto
Events in Etobicoke · 10 guests

Affordable Yacht 27' Doral in Toronto

5.0
$160+/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
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
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
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
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
Snoozed - Active 02 Jun 2026

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. 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!

  3. 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!

  4. 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!

  5. 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.

  6. CD

    Courtney

    Private Sail from Brooklyn Bridge Park

    This was such an incredible experience. The captain was amazing and was very well informed about sailing and NYC. Planned this for a surprise birthday party and it was a fabulous time. I absolutely recommend and hope to do this again soon! Note, bring extra layers becuase it can get very chilly!