Great sailboat rentals near Stamford, Connecticut.

Average of 51 reviews in this area.
3 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. ND
    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.

  2. NS
    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. PF
    Charter Sailboat Cruiser in Stamford, Connecticut

    Marco was friendly and knowledgeable throughout the whole experience. My group of 6 people fit comfortably on the vessel, and would definitely look forward to book with Marco again!

  4. DK
    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Rick was amazing and his boat was perfect for a larger group. He offered us an amazing time and great hospitality. We shared many laughs and many great stories. I would recommend it for anyone and you could not pick a better host. The boat was capable of hosting a party of 8-10 comfortably with plenty of room to lounge and take in the sun. Super clean and super well kept. He also offers several great historic pieces about the area and don’t forget to ask him about the jacuzzi!!!

  5. ET
    Charter Sailboat Cruiser in Stamford, Connecticut

    omgosh first time ever on a boat .Marco was soo cool and friendly we learn few things today . we had a blast definitely booking again .Marcossss you rock thank youuuu for a awesome evening

  6. IM
    Charter Sailboat Cruiser in Stamford, Connecticut

    We had a great time! The weather was good. The boat is beautiful Hunter and kept in tip top shape. Marco is a great captain, very knowledgeable. We felt very safe with him at the helm. Will definitely repeat!