The Best Sailboat Rentals Near Fire Island

Experience premier service: NYC’s longest-running private sailing charter

We had an amazing experience with Captain L! He was incredibly attentive, professional, and made sure everything went perfectly for us. The whole trip felt smooth, relaxing, and very special thanks to him. Highly recommend to anyone looking for a great time on the water!

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

We are still talking about our time aboard The Genesis! Eric was so welcoming to our family, ages 2 - 70! A true sailor, Eric took us on a two-hour sail from Chelsea Piers to the Statue of Liberty. He shared his endless knowledge about NYC as we passed spots of interest on the shoreline. Eric was super kind and patient with our 5-year-old grandson, allowing him to steer the boat. That experience was priceless. The Genesis is a wonderful sailboat that has been lovingly and meticulously cared for. Thank you, Eric, for helping us celebrate Nick's 70th birthday. It was perfect!

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

Our sail with David was wonderful! He’s so nice and had some great ideas for pictures for our engagement shoot!

Chaparral 256 Family Cabin Cruiser

we highly recommend eli as a captain - he was very accommodating & easy communication, great boat and enjoyable experience! 5+ star!

Sail From Northport or Huntington, NY

Mark is a wonderful captain and person all around. He is very communicative and informative both before and while we were on his sailboat. We had the best time sailing from Huntington to Northport. He sang a Happy Birthday to our Mom and brought out his guitar! Thanks so much, Captain Mark!

Sail From Northport or Huntington, NY

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!