The Best Sailboat Rentals in Long Island

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

Mark was super cool, and we had a great time overall. The only issue was that the zodiac boat at the front was blocking access to the bow, so we couldn’t use that part of the boat. We also wanted to swim, but there was probably a miscommunication — we ended up eating during the time we should’ve been swimming, and later Mark said it was too late. That was a bit disappointing, as we didn’t get to swim at all during our 4-hour trip. Everything felt safe and nice overall. Mark let us play any music we wanted, and everything was clean. A longer trip with more time would definitely be a better option next time.

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

This charter was the perfect little getaway—a mini vacation on the water that left us completely refreshed. The boat was exactly as described: clean, comfortable, and clearly cared for with pride. Every moment felt relaxing and easy, from the smooth ride to the peaceful surroundings. It was the kind of experience that makes you forget about everything else for a while—in the best way. Highly recommend for anyone needing a short but sweet escape.

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

Marco is the consummate professional/captain. Flexible on the water with things to do and we all had a blast cruising and diving and swimming in the Sound

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

Steven was an amazing and communicative captain! He let us help sail and was completely flexible with the route. 10/10 experience & made bday so special.

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

Steven F. did a great job. We had a wonderful time. We enjoyed his nautical expertise as well as his engaging, friendly, and entertaining personality.