The Best Sailboat Rentals Near Candlewood Lake

Classic Beauty: Nautor Swan 46' Bluewater Cruiser, Sag Harbor, New York

Captain Alan and his boat are incredible!! We brought a group of girls for a bachelorette trip and spending the day out on the water was SO much fun. Captain Alan was so communicative and helpful throughout the process and leading up to the day of our charter. He had everything we could have needed on board and was so helpful the whole trip!! His deckie was also so incredibly helpful - we could not have asked for a better time!!! He even had floats and a paddleboard to use which was awesome. Highly recommend to anyone looking for a fun day on the water!! 10/10, no notes!!

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.

Woman-owned luxury with transparent pricing - read our 5-star reviews!

Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!

Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person

Mark’s boat is spacious. I had booked the boat during the sunset hours and the views were amazing. Mark provides detailed instructions for the pickup and is very punctual.

The Only 40ft Hinckley Sailboat in Manhattan

Captain Andy was amazing- super accommodating and flexible. We got EPIC engagement pictures , while also having the best experience :). only amazing things to say!

Sailing NYC aboard 34' Catalina

Ian provided us with a fantastic sailing experience for our wedding anniversary. It was absolutely lovely—truly beyond our expectations. His communication and instructions were clear and outstanding from start to finish. On the day of our sail, Ian even reached out to offer an earlier time slot when one became available, which we appreciated. The boat was perfect, and we had an unforgettable time on the water. Thank you, Ian, for making our special day even more memorable!