The Best Sailboat Rentals Near Westbrook

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!!

Custom Sailing Charter - Newport/ Block Island

We really enjoyed our sail with Candace, Stephanie and Matt - and we can't forget Eddie Spaghetti the daschaund! They told us a lot about the history of the area and made sure we were comfortable and well-taken care of on this sail. Many thanks to Stephanie too for the wonderful photos on the trip.

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.

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!

The Only 40ft Hinckley Sailboat in Manhattan

We had the sunset trip and it was amazing! Both Andy and his assistant were great… the views… OMG I absolutely recommend it!