The Best Sailboat Rentals Near Greenport

Sailing NYC aboard 34' Catalina

We had such a great evening sailing around NYC! Andrew was a wonderful host and captain and even went out of his way to help one of our group struggling with motion sickness. We enjoyed the route and putting up the sail in the harbor! Overall, it was an awesome experience, and I would definitely recommend booking for a fun and memorable experience!

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

We had an absolutely perfect experience with our captain! From start to finish, everything was seamless—professional, friendly, and so attentive. The boat was in excellent condition, and the captain made us feel safe and comfortable the entire trip. His knowledge of the area and smooth handling of the boat made the day unforgettable. We couldn’t have asked for a better experience. Highly recommend!

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!

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

Nina is a fantastic person, fantastic captain and a fantastic company. 2 of us and a doggie went on a short adventure with her and it couldn’t have been a better experience. We had so much fun, laughter and comfort with her on her boat that i can barely put this in words. We will definitely do this over and over again. Highly recommend!

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!

The Only 40ft Hinckley Sailboat in Manhattan

I highly recommend chartering Captain Andy's sail boat! Everything in the listing was exactly as described and his boat was perfect for a day on the water. He answered all of our (admittedly dumb) questions about NYC and was super friendly and took plenty of photos of us when asked. I have no complaints and would definitely charter Captain Andy's boat again!