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    Incredible sailboat rentals in Long Island, United States.

    Average of 78 reviews in this area.
    6 listing
    Charter Sailboat Cruiser in Stamford, Connecticut
    hour$195
    6 guest

    Charter Sailboat Cruiser in Stamford, Connecticut

    Luxury 51' Lagoon Catamaran on Long Island Sound
    hour$575
    6 guest

    Luxury 51' Lagoon Catamaran on Long Island Sound

    Flying Scot Windsurfing in Brookhaven, New York
    hour$125
    5 guest

    Flying Scot Windsurfing in Brookhaven, New York

    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 customer reviews for Sailing in Long Island.

    1. Jean
      Jean
      Charter Sailboat Cruiser in Stamford, Connecticut

      Marco is a great captain - really knowledgeable and generous with sharing stories of his experiences. Know this is a tour on a sailing cruiser - sails will not go up. It’s a great circular tour around Stamford Harbor under motor.

    2. 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.

    3. BS
      Bonnie
      Charter Sailboat Cruiser in Stamford, Connecticut

      Marco is the perfect captain. Extremely knowledgeable about boats, navigates the waterways with great confidence, and truly loves what he does. The boat is very clean, maintained beautifully, and the day was perfect. I would definitely sail with Marco again. Great experience!

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

      Capt. Rick was so fun! His knowledge of sailing and expertise made him a wonderful guide. Plus he is so personable! You can tell he really enjoys the water and loves to share the joys of being on the water with his guests! The boat was great and well outfitted! Such a wonderful experience!! I highly recommend! The trip on Capt. Ricks boat was so memorable and special! It made my 40th birthday an event to remember!

    5. Denis
      Denis
      Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

      Rick was amazing and his boat was perfect for a larger group. He offered us an amazing time and great hospitality. We shared many laughs and many great stories. I would recommend it for anyone and you could not pick a better host. The boat was capable of hosting a party of 8-10 comfortably with plenty of room to lounge and take in the sun. Super clean and super well kept. He also offers several great historic pieces about the area and don’t forget to ask him about the jacuzzi!!!

    6. AF
      ASHLEY
      Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

      Rick was passionate about his love for the water and for the art of sailing, he answered the questions the kids had, he even answered mine. He was great with the kids, pirate flags and buried treasure had them engaged from the start. The boat was incredible, the ride was comfortable and Rick was warm and inviting. I highly recommend sailing with Rick.

    GetMyBoat has 6 listing for Sailing experiences in Long Island with 78 review.

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