United StatesConnecticut

Incredible sailboat rentals in Connecticut, United States.

Average of 39 reviews in this area.
10 listings

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. 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!

  2. JL
    Jessica
    42' American-built Catalina Cruising Monohull Rental 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!

  3. NC
    Nathalie
    Sail on the classy 35' "Nomade" Yacht in the Thimble Islands, Connecticut

    Eric was a gracious host. His boat was divine and equipped with everything we needed. He sailed us around the Thimble Islands where we swam and took in the glorious surroundings. A perfect way to spend your 50th birthday. Merci beaucoup, Eric!

  4. GR
    Gillean
    Captained Sailboat Charter in Salisbury

    Nina was great, and the sail was so relaxing and peaceful. Not too many powerboats out like you see on so many other lakes, so it was smooth sailing all the way. I’d highly recommend a sail with Captain Nina on this lovely lake.

  5. CD
    Carolyn
    Sail on the classy 35' "Nomade" Yacht in the Thimble Islands, Connecticut

    Had a wonderful time with Captain Eric on Nomade even though the wind seemed to be missing that day. He made sure all of us felt included in the sailing experience and we all left the boat in a happy mood. Thanks, Eric.

  6. CF
    Christian
    42' American-built Catalina Cruising Monohull Rental in the Hamptons

    Had a fantastic time with Nate on his sailboat. Our group arrived late and he was able to keep us out for an additional hour. Very considerate and friendly, enjoyed hearing about his sailing adventures. Hope to be back!