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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 349 listings

High Demand
 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
$240+/hour
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Caribbean Vibez on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez on a Brooklyn Sailboat

5.0
Superowner
$191/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
High Demand
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Sail the Hudson River in Kingston
Sailing in Kingston · 6 guests

Sail the Hudson River in Kingston

5.0
$125/hour
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
$475/hour
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
$300/hour
Limited Availability
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
High Demand
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/hour
Limited Availability
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$321/hour
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

5.0
$196+/hour
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
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
$225+/hour
Instant Book
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$107/hour
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/hour
Jeanneau 39i Julia Sailing Yacht in NY Harbor
Sailing in Manhattan · 6 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$400/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
Cruise Long Island Sound Aboard 62ft Lagoon 620 Catamaran in Greenwich, CT
Sailing in Greenwich · 12 guests

Cruise Long Island Sound Aboard 62ft Lagoon 620 Catamaran in Greenwich, CT

5.0
$1,500/hour

Sailing Reviews in New York

  1. 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!

  2. PR

    Prapsede

    One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

    Sorry for the very late review! I took this boat ride about 3 years ago, and it was such an amazing experience. The views were beautiful, the ride was relaxing, and I had a great time. Gene and his crew took care of us and made my sisters party amazing. Highly recommend!

  3. ST

    Shaddy

    56' SeaRay Yacht in New York!

    We had an incredible experience aboard Encore with Captain Max! I booked the boat for my engagement, and when rain threatened our original date, Max was extremely understanding and worked with me to move the reservation so the moment could still be everything I had planned. He was communicative, flexible, and genuinely invested in helping make the occasion special. The boat was beautiful, clean, comfortable, and exactly as advertised. Once we were aboard, Max made us feel completely at ease and gave us the perfect experience on the water. This was one of the most important and memorable days of our lives, and Max played a huge role in making it happen. I truly appreciate how accommodating he was throughout the entire process. I couldn’t recommend Captain Max and Encore more highly!

  4. Kim

    Kim

    Sail in downtown Toronto

    Dominic was incredible! He was so chill and so kind with our family. It was a perfect day out sailing on the water. He taught us so much, shared stories, local history and was genuinely so sweet with our family, taking pictures and showing us points of interest! A PERFECT EXPERIENCE AND A PERFECT DAY!

  5. CP

    Colleen

    Sail in downtown Toronto

    We had a fabulous afternoon sailing with Captain Dom. He was very welcoming, friendly and knowledgeable. We immediately felt safe and comfortable sailing with him. The boat was clean and very comfortable and the vibe was relaxing and chill. We enjoyed being out on the lake with the great views of the skyline. It’s a great way to unwind and spend some quality time with some family or friends. I would definitely recommend this experience and I will be booking again to sail with Captain Dom.

  6. EC

    Ehsan

    Sail in downtown Toronto

    We had a great night with Dom. He was very friendly, kind, and easy to talk to, and made the whole experience enjoyable from start to finish. He also took so many great photos of us, and we’ll always have those memories. We had an amazing time and would definitely recommend this tour to anyone. Thanks again, Dom!