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All listings in New York

Incredible sailboat rentals in New York, United States.

Page 1 of 247 listings

Limited Availability
Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
 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
Limited Availability
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
#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
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
Sail in downtown Toronto
Sailing in Toronto · 6 guests

Sail in downtown Toronto

5.0
$119/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
High Demand
Private Sail from Brooklyn Bridge Park
Sailing in Manhattan · 6 guests

Private Sail from Brooklyn Bridge Park

5.0
Superowner
$230/hour
Limited Availability
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
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
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
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
$321/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
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
$208+/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
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 Reviews in New York

  1. SV

    Stacey

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

    Nate is truly the best of the best if you’re looking to book a boating experience! There are individuals who distinctly stand out for good reason and Nate is one of them through and through.

  2. 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!!

  3. MA

    Melis

    Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

    Ian is the absolute best! He took us out for an amazing trip and we had the best time ever! He knows what he’s talking about when he says “you should see new york city at night”!

  4. Laura

    Laura

    Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

    I would highly recommend sailing with Captain Steve! He is extremely knowledgeable and an excellent sailor. We loved our sail with him!

  5. 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!

  6. Jahaan

    Jahaan

    56' SeaRay Yacht in New York!

    We had an absolutely fantastic day out on the water with this private boat. From start to finish, everything was well organized, relaxing, and enjoyable. The boat was clean, comfortable, and perfect for taking in the beautiful scenery. Our captain was friendly, knowledgeable, and made sure everyone felt welcome and safe throughout the trip. We loved having the flexibility of a private boat, allowing us to explore at our own pace and enjoy some truly memorable views. We would highly recommend to anyone looking for a fun, relaxing, and personalized day on the water. We can't wait to do it again!