The Best Sailboat Rentals Near Middletown

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!

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!

Caribbean Vibez on a Brooklyn Sailboat

I rented the chef and boat package for my sister’s birthday. Johnny was great with communication and gracious with his time as we were running late. Chef Lioness’s food was amazing. The music, the food and the tour was awesome. This experience was worth every penny!!

Caribbean Vibez on a Brooklyn Sailboat

For a 3 hour Caribbean experience without a flight, passports and customs PLEASE join Capt Johnny! The vibes are superb, the company perfect and add on the bonus of having Lioness with a delicious menu aboard and you will have an amazing time. Pick up was on time, Capt. Johnny was docked waiting for us. He was knowledgeable of the sights, navigation and safety. My wife is usually running for the life vest out of uneasiness on boats. With Capt. Johnny she didn’t mention a life vest once (although they were readily available). Born and raised in New York, I saw and was educated on sites that I have never seen. Lioness provided a meal that could have easily come from a 5 star restaurant’s kitchen. The four course meal was seasoned to perfection. I have NEVER enjoyed Brussels sprouts to the point of wanting a second helping!!!! We left this experience wanting more time!!! I highly recommend Capt. Johnny and Lioness!! You will not regret it!!

Caribbean Vibez on a Brooklyn Sailboat

Thank you Johnny for a wonderful day! It was cloudy and high chance of rain on the day of our initial booking but he changed it to accommodate the weather and our safety. He was great! He was calm just like the waves. Johnny is a great captain. He provided his speaker so we felt comfortable on his vessel. He made us feel at home and we would definitely book again. Please book with Johnny too!