United StatesConnecticut

Incredible sailboat rentals in Connecticut, United States.

Average of 71 reviews in this area.
11 listings
Charter Sailboat Cruiser in Stamford, Connecticut
hour$195
New YorkLong IslandCruising Monohull
6 guests

Charter Sailboat Cruiser in Stamford, Connecticut

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

Luxury 51' Lagoon Catamaran on Long Island Sound

42' Catalina Sailing Yacht in the Hamptons
hour$300
New YorkLong IslandCruising Monohull
6 guests

42' Catalina Sailing Yacht in the Hamptons

Beneteau 57' Luxury Sailing in Sag Harbor
hour$750
New YorkLong IslandCruising Monohull
10 guests

Beneteau 57' Luxury Sailing in Sag Harbor

Captained Sailboat Charter in Salisbury 2 hr sails
hour$85
SalisburyBeach Catamaran
4 guests

Captained Sailboat Charter in Salisbury 2 hr sails

Charter on 50ft Beneteau Sailing Yacht in Greenport, New York
hour$275
New YorkLong IslandCruising Monohull
6 guests

Charter on 50ft Beneteau Sailing Yacht in Greenport, New York

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

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

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. JL
    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. ND
    Natasha
    Charter Sailboat Cruiser in Stamford, Connecticut

    Marco was such a gracious captain. We were a group of four adults just relaxing on the boat cruising around. Marco was very polite, accommodating and knowledgeable. I highly recommend booking his boat.

  3. EC
    Ethan
    Beneteau 57' Luxury Sailing in Sag Harbor

    the team had a great time, we really enjoyed our experience and will def be coming back!! def recommend!

  4. 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.

  5. VW
    VICKI
    Charter Sailboat Cruiser in Stamford, Connecticut

    our family had an amazing time and Marco went above and beyond to make our experience memorable he is super sweet and professional as well

  6. JR
    JACLYN
    Charter Sailboat Cruiser in Stamford, Connecticut

    Great experience on the water. Communication leading up to depature was great. Highly recommened for a great time.