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    All listings in New York

    Incredible sailboat rentals in New York, United States.

    5.0
    (870 Reviews)

    Page 1 of 4 • 76 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    $240+/hour
    Instant Book
    The Only 40ft Hinckley Sailboat in NYC Harbor – Sail in Style!
    Sailing in Manhattan · 6 guests

    The Only 40ft Hinckley Sailboat in NYC Harbor – Sail in Style!

    5.0
    $285/hour
    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
    Sailing in Sag Harbor · 6 guests

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

    5.0
    $600/hour
    35ft C&C 35 Sailboat in Toronto
    Sailing in Etobicoke · 6 guests

    35ft C&C 35 Sailboat in Toronto

    5.0
    $179/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
    27 Foot Sailboat for a Day of Fun in the Sun in Toronto
    Sailing in Toronto · 6 guests

    27 Foot Sailboat for a Day of Fun in the Sun in Toronto

    5.0
    $54/person
    #1 Manhattan Sailboat! 5-Star Champagne & Catering Service with Captain & Crew
    Sailing in Manhattan · 6 guests

    #1 Manhattan Sailboat! 5-Star Champagne & Catering Service with Captain & Crew

    5.0
    Superowner
    Best of 2023
    $290/hour
    Instant Book
    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
    Tours in Stamford · 6 guests

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    4.9
    Superowner
    $180+/hour
    Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
    Sailing in Norwalk · 12 guests

    Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

    4.7
    Superowner
    Best of 2023
    $33/person
    Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
    Sailing in Huntington · 10 guests

    Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

    5.0
    Superowner
    Best of 2023
    $33/person
    Woman-owned luxury with transparent pricing - read our 5-star reviews!
    Sailing in Manhattan · 6 guests

    Woman-owned luxury with transparent pricing - read our 5-star reviews!

    5.0
    $285/hour
    56' SeaRay Yacht in New York!
    Events in New York · 12 guests

    56' SeaRay Yacht in New York!

    4.7
    $475/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 ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available
    Sailing in Sag Harbor · 6 guests

    42' Catalina ailing Yacht - Two Hour Sailing Charter - Sunset Sail Available

    New
    $400/hour
    A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups
    Sailing in Sag Harbor · 25 guests

    A Luxuriously Appointed USCG Certified Trimaran Large and Small Groups

    5.0
    $850/hour
    Sail in downtown Toronto
    Sailing in Toronto · 6 guests

    Sail in downtown Toronto

    5.0
    $72/person
    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
    Best of 2023
    $475/hour
    42' Catalina Sailing Yacht in the Hamptons - 4 Hours
    Sailing in Sag Harbor · 6 guests

    42' Catalina Sailing Yacht in the Hamptons - 4 Hours

    5.0
    $325/hour
    Sailing NYC aboard 34' Catalina
    Sailing in Manhattan · 6 guests

    Sailing NYC aboard 34' Catalina

    5.0
    Superowner
    $220/hour
    Sailboat on the Hudson
    Sailing in Ossining · 6 guests

    Sailboat on the Hudson

    New
    $150/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
    $325/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
    $225+/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
    A Tropical Experience on a Massive Sailing Trimaran
    Sailing in Toronto · 12 guests

    A Tropical Experience on a Massive Sailing Trimaran

    4.9
    $323/hour

    Top Destinations Nearby

    Sailing Reviews in New York

    1. MC

      Monica

      Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

      Ian is absolutely wonderful. I wanted to celebrate my 30th birthday and it was a rainy weekend, and Ian was SUPER FLEXIBLE in booking around good weather, like he truly and genuinely cared about us having a good experience. Great human!!!

    2. GS

      Gurpreet

      Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

      Ian did a great job with our trip. He was able to show us all around nyc and even though we were running close to the sunset, he was able to get us out on the water in time to watch. The boat ride was smooth, he was very accomodating. It was fun chatting with him and he came prepared with blankets, jackets, water if needed. The boat trip itself was smooth with no issues. Would definitely book again, if needed and highly recommend!

    3. RC

      Roman

      35ft C&C 35 Sailboat in Toronto

      We (dad+mom+7yo son) had an amazing 2-hour trip with Peter in Sep 2024! Enjoyed very much every minute of it. Learned a lot about sailing and had a chance to try it out under the captain's guidance. And we really really enjoyed the conversation with Peter. I definitely recommend Peter and his boat "Restless" !

    4. JT

      Julia

      Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

      We had an amazing experience with Ian! The boat was beautiful and the route we took was too! Ian made sure we were comfortable the whole time, and took good care of us. We couldn’t have asked for any more, it was perfect. Thank you!!

    5. MC

      Mike

      Sailing NYC aboard 34' Catalina

      Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!

    6. JD

      Jessica

      35ft C&C 35 Sailboat in Toronto

      I had an amazing experience with Peter and Simon. Would recommend this experience to anyone.

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