Great sailboat rentals near Stamford, Connecticut.

Average of 28 reviews in this area.
2 listings

Step onboard a sailboat for an unforgettable experience in Stamford, Connecticut.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Stamford, 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. Stamford, Connecticut is a wonderful sailboat rental destination.

Using GetMyBoat to rent your next sailboat.

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.

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GetMyBoat customer reviews for Sailing in Stamford.

  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. 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.

  3. CC
    Cherise
    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Captain Rick was a gracious host, he made us feel at home on his boat. He was every engaging and so very funny! He displayed such patience with our children and even let our son steer the boat. Can't wait to book with him again!!

  4. LY
    Lizzie
    Charter Sailboat Cruiser in Stamford, Connecticut
  5. EL
    Esther
    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Captain Rick is the man! He is great to sail with. He is calm and easy to be with. We highly recommend him. He will be our first go to person for future sailings.

  6. RB
    Robert
    Charter Sailboat Cruiser in Stamford, Connecticut

    Very friendly and accommodating, making sure all of us enjoyed ourselves. Beautiful boat. The six of us had a wonderful time. We’d definitely pick Marco again.