The Best Sailboat Rentals Near Greenport

Sail From Northport or Huntington, NY

Captain Mark hosted us for my boyfriend’s surprise birthday party. Mark was extremely easy to plan with, accommodatingly sailed out of a more convenient port for us, and took us to two swim spots! The day was described as “the best outing ever” by many of our friends.

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

We had a fantastic day out with Captain Andy! He is a total pro and made the whole day very easy, comfortable, and fun. The boat is gorgeous, and Andy had everything we needed aboard. Highly recommend!!

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Yesterday’s sailing experience was simply amazing. The captain and crew went above and beyond to take care of our family and make sure all of our needs were met. Even when we were caught up in the moment, they made sure to point out the incredible sights and beauty of the Vineyard so we would not miss a thing. Their kindness, attention to detail, and genuine care made the whole experience unforgettable. We had such a wonderful time and will definitely charter with them again when we return.

63' Catamaran - Newport, RI - Luxury sailing for large groups!

Thank you so much for having us last night! It was truly the BEST boat experience any of us had ! The Captaint and Kiki were the best hosts ! Super helpful and fun !! They exceeded our expectations and the boat was amazing ! Will definitely make this a yearly thing !!!

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

This was actually the best day of my life. I had my bachelorette and the boat was so incredible, Brian and his partner are amazing hosts and their boat is so gorgeous and special. They were flexible with the hours and very accommodating. Would love to rebook !!

Sail From Northport or Huntington, NY

Great captain, great experience. First time sailing for me and felt as comfortable as ever. Seamlessly kept me informed on the goings on with sailing so I felt at peace knowing what was happening. The boat was comfortable and safe. Captain mark was accommodating and friendly, good heart, good vibes! You'd be lucky to Have Captain Mark!