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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 351 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
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
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
$319/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
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
$195+/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
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
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$250+/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

Sailing Reviews in New York

  1. 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!

  2. 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!

  3. CF

    Carlos

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Captain Marco was absolutely amazing! He was incredibly attentive to our entire group throughout our birthday party celebration and truly went above and beyond. His energy and hospitality made it such a special and memorable day for all of us. We would definitely recommend him to anyone looking for a perfect day on the water and we are already planning our future boat adventures with him!

  4. JK

    Junghun Jemma

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    With Ian, our special 250th July 4th celebration became even more unforgettable. From the marina, we enjoyed spectacular views of the fireworks. What made the evening truly exceptional was Ian's personalized dock tour—something only possible because of his close relationship with the marina. It gave us experiences we never expected, including seeing the historic tall ships, watching the special boats on the river, and getting a close look at the Macy's fireworks barges as they prepared for the show. Ian went out of his way to make sure our family had a remarkable experience. Seeing my granddaughter dancing on the deck of his romantic sailboat to the music Ian thoughtfully selected, with the fireworks lighting up the sky in front of her, is a memory we will cherish forever. Thank you, Ian, for making our Independence Day celebration so magical. We will definitely be back on your sailboat for another special occasion soon!

  5. Gretchen

    Gretchen

    Sail the Hudson River in Kingston

    Cannot say enough about this experience. Loved the whole trip, great team at the helm, easy and accommodating and fun to spend the morning with. Highly recommend. Thank you so much!

  6. Andrew

    Andrew

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is a wonderful host! We had a romantic evening on his boat, getting to see the sunset and the city. Ian is very responsive, professional, and gracious, we definitely recommend him!