We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

GetMyBoat Logo

    Incredible sailboat rentals in Long Island, United States.

    Average of 86 reviews in this area.
    7 listings
    Sail From Northport or Huntington, NY - $225/Hour
    person$75
    Super Owner12 guests

    Sail From Northport or Huntington, NY - $225/Hour

    Sail from Norwalk, CT - $220/Hour
    hour$265
    Super Owner12 guests

    Sail from Norwalk, CT - $220/Hour

    Sail From Port Washington, NY - $215/Hour
    hour$215
    Super Owner12 guests

    Sail From Port Washington, NY - $215/Hour

    Charter Sailboat Cruiser in Stamford, Connecticut
    hour$195
    6 guests

    Charter Sailboat Cruiser in Stamford, Connecticut

    Sailing Long Island Sound with Captain Steve
    hour$225
    6 guests

    Sailing Long Island Sound with Captain Steve

    Private Schooner in NY
    day$1,500
    6 guests

    Private Schooner in NY

    GetMyBoat customer reviews for Sailing in Long Island.

    1. DE
      Desireé
      Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

      Captain Rick was excellent!!! He is a skilled and patient captain. We had so much fun on the trip. Lots of laughs and great conversations. This day could not get any better. The boat and amenities were as advertised. I will definitely book this trip again with Captain Rick!

    2. KC
      Kellie
      Charter Sailboat Cruiser in Stamford, Connecticut

      We booked our trip last minute with Marco and he was very fast to respond and helpful. It was such an easy process and we had such a great time. Marco was fantastic and we can’t wait to come back!!

    3. BF
      Brigitte
      Sail from Norwalk, CT - $220/Hour

      Wonderful trip, easy and very enjoyable. Capt Mark was great. Strongly recommend that you spend a special boat trip with The Naked Truth and Capt Mark

    4. GM
      Geovanna
      Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

      The best experience of our lives. My mom had the greatest birthday ever. Captain Rick is amazing. We’re extremely grateful for his great attitude and help putting this together. He made this experience 10x better. Thank you Captain Rick!!

    5. CJ
      Christiana
      Sail From Northport or Huntington, NY - $225/Hour

      Mark was an entertaining host. Definitely recommend his services !!

    6. NS
      Nicholas
      Charter Sailboat Cruiser in Stamford, Connecticut

      Marco was a wonderful captain and we had a great time watching fireworks from Todd's Point on the water. He piloted the ship safely and got us "front row seats" for the show. He also was mindful of other boaters in the area and got us out before the show ended so we weren't stuck or in danger. This was a surprise for my partner and Marco made it so worth the wait to reveal that we were going on an adventure in this beautifully renovated, fully equipped and well maintained ship. Would do this trip over 100 times! I highly recommend Marco for anyone that wants a safe, comfortable, and truly special time on the water.

    Boating Guide - Long Island Sailing

    Rent or charter a sailboat for a memorable experience in Long Island.

    Are you ready for a fun adventure out on the open water onboard a sailboat in Long Island? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Long Island is a wonderful sailboat rental destination.

    Using GetMyBoat to book your next sailing experience.

    Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

    Search for the perfect experience now and book your dream day out on the water.

    GetMyBoat has 7 listings for Sailing experiences in Long Island with 86 reviews.

    Search Long Island