Longshore Sailing School in Westport offers camp-style one-week junior courses for ages 8–16 on Long Island Sound, covering sailing, catamaran sailing, racing, kayaking, and paddleboarding, with no experience required. Private instruction is available for ages 5 and up, and boats and boards are rented by the hour through the summer.
The practical details
We list only what the camp itself publishes, and programs change — dates, prices, ages and availability can all move after we check. Confirm the details on the camp’s own website and contact Longshore Sailing School directly before you register or pay. Last checked August 2026.
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★★★★★Moira Geraghty SchneiderLongshore Sailing School is the best! Their sailing programs are very well run. My child has been taking courses there for many years and always comes home happy to share about a new skill. On weekends we use them to rent kayaks and the staff is always friendly and helpful. LSS is a tremendous asset to our community and even organizes events to help clean up the sound. I have also seen them give away spots in camp to kids in the community. All around a top-notch spot to enjoy the beautiful sound.
★★★★★Patrik ErlmannWe love Longshore Sailing, their classes and summer programs are great fun and all the boats are in perfect condition. Rentals are easy via the web page and the staff is super friendly and helpful. The area is great for beginners and has lots of wind!
★★★★★Deirdre GriffinI have had two private sailing lessons this week and they were both fabulous. Eva, on Tuesday was so encouraging and patient. She went above and beyond after the 'hands on lesson aboard the Quest;' she wrote out two pages of notes with the key points of the lesson. Today (Friday, July 19th), Ari took myself along with my teenage niece and nephew out for a lesson and spectacular experience. He offered encouragement for them to participate but did not push. He was flexible to the situation, knowledgeable and adept with his skill as well as his ability to impart this information. I am excited and inspired to keep going with lessons. I cannot say enough about the professionalism of the instructors and the responsiveness of Jane, the director of the program. Thank you Longshore Sailing School.
★★★★★Melissa ClarkJane and everyone at the Longshore Sailing School were absolutely phenomenal. From kayaking, to sailing, to learning, the whole team is happy to help you have the best day out on the water. Could not imagine a better place to relax, enjoy and have fun with the whole family (or friends) ☺️
★★★★★Katy O'MeliaI went to the sailing school as a kid and loved it. I found out about their boat rentals, which are very reasonably priced, and was so excited. They make sure everything is ready for you, have life jackets if you don’t have your own, and are always friendly and helpful! And of course, being on the water is the best.