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    Incredible sailboat rentals in Connecticut, United States.

    Average of 69 reviews in this area.
    11 listings
    Charter Sailboat Cruiser in Stamford, Connecticut
    hour$195
    6 guests

    Charter Sailboat Cruiser in Stamford, Connecticut

    42' Catalina Sailing Yacht in the Hamptons
    hour$300
    6 guests

    42' Catalina Sailing Yacht in the Hamptons

    Charter 36ft Sloop In Westbrook, Connecticut
    person$145
    6 guests

    Charter 36ft Sloop In Westbrook, Connecticut

    Beneteau 57' Luxury Sailing in Sag Harbor
    hour$600
    6 guests

    Beneteau 57' Luxury Sailing in Sag Harbor

    35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York
    hour$300
    6 guests

    35ft Dufour 4800 Sloop Boat Charter in Sag Harbor, New York

    Sail or Cruise! Classic Schooner/ Stable/ Comfortable & Fun!
    hour$1,000
    25 guests

    Sail or Cruise! Classic Schooner/ Stable/ Comfortable & Fun!

    Boating Guide - Connecticut Sailing

    Rent or charter a sailboat for a memorable experience in Connecticut.

    Are you ready for a fun adventure out on the open water onboard a sailboat in Connecticut? 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. Connecticut 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 Connecticut.

    1. NT
      Nicole
      42' Catalina Sailing Yacht in the Hamptons

      Everyone had a great time. The crew was very welcoming and friendly. Overall fantastic experience. Thank you!

    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. Ilona
      Ilona
      42' Catalina Sailing Yacht in the Hamptons

      We had a great day out on the water with Nate! He was very flexible with starting a bit later due to the weather and had great communication overall. He and his crew are very kind and professional. The boat is great and this is a must-do while you are in the Hamptons!

    5. JL
      Jessica
      42' Catalina Sailing Yacht in the Hamptons

      Our trip with Nate was awesome. He is a great host and made our trip incredibly comfortable and fun. He took us on a great route - where we were able to swim in clear waters, and get a good view of surrounding areas. Highly recommend! Went way above our expectations!

    6. Lauri
      Lauri
      Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

      CaptIn Eric provided an amazing experience for my family. Not only did he display his professional sailing skills but he accommodated time for dining and swimming and the thrill of being under sail on a beautiful sunny and windy day. We've already shared our great experience with friends and family and hope to join them for another trip on Erics Nomade.

    GetMyBoat has 11 listings for Sailing experiences in Connecticut with 69 reviews.

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