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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 248 listings

 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
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
Limited Availability
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
Instant Book
#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
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
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
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
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Caribbean Vibez on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez on a Brooklyn Sailboat

5.0
Superowner
$191/hour
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

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

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
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
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
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
$327/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
$220+/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
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
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
Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

5.0
$310+/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. PC

    Peter

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    Had a GREAT day on the sound with Captain Rick. His boat is in excellent condition clean comfortable and so well maintained. Rick is a very experienced sailor with whom we always felt safe. He showed us all over Long Island Sound, which he knows so well. I highly recommend Rick for a great day on the water!!

  2. CE

    Celebi

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

    We had an amazing experience with Captain L! He was incredibly attentive, professional, and made sure everything went perfectly for us. The whole trip felt smooth, relaxing, and very special thanks to him. Highly recommend to anyone looking for a great time on the water!

  3. BH

    Bibiana

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

    We are still talking about our time aboard The Genesis! Eric was so welcoming to our family, ages 2 - 70! A true sailor, Eric took us on a two-hour sail from Chelsea Piers to the Statue of Liberty. He shared his endless knowledge about NYC as we passed spots of interest on the shoreline. Eric was super kind and patient with our 5-year-old grandson, allowing him to steer the boat. That experience was priceless. The Genesis is a wonderful sailboat that has been lovingly and meticulously cared for. Thank you, Eric, for helping us celebrate Nick's 70th birthday. It was perfect!

  4. NH

    Nicole

    Private Sail from Brooklyn Bridge Park

    We loved getting up close to the statue of liberty ! Mike really showed us some beautiful sights! He was so great! Excellent experience top to bottom!

  5. demetrios

    demetrios

    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Would recommend hands down! NYC has a lot of boats and operators but dealing directly with an owner/operator is so much better.

  6. Maria

    Maria

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    We had an absolutely perfect experience with our captain! From start to finish, everything was seamless—professional, friendly, and so attentive. The boat was in excellent condition, and the captain made us feel safe and comfortable the entire trip. His knowledge of the area and smooth handling of the boat made the day unforgettable. We couldn’t have asked for a better experience. Highly recommend!