United StatesConnecticut

Incredible sailboat rentals in Connecticut, United States.

Average of 8 reviews in this area.
12 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. 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.

  2. CO
    Clayton
    Catatonic 500, Luxury 51' Catamaran for Long Island Sound

    Dirk and Sandy provided a great experience. They were great with our kids, 8 & 5, and knew when to engage or step back and allow family time. The boat was beautiful and spacious. We look forward to going back.

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

    Eric and Sylvia are a great team. Been sailing for years. Boat is well kept and comfortable. Thimber islands are great area to sail around and just relax in the widest part of the Sound.

  4. SO
    Steve
    Catatonic 500, Luxury 51' Catamaran for Long Island Sound

    Fantastic day out on the water! Dirk and Sandy could not have been more accommodating or friendly. Highest recommendation!

  5. RS
    Remington
    Charter 36ft Sloop In Westbrook, Connecticut

    Great time and great crew... look forward to seeing them again!

  6. LP
    Lauren
    Catatonic 500, Luxury 51' Catamaran for Long Island Sound