Longshore Sailing School: A Brief History

Established over 60 years ago, Longshore Sailing School is well-known as one of the oldest, largest, and most celebrated community sailing programs in the country. Operating seasonally, LSS conducts an extensive selection of classes (ages 8 through adult) and hourly boat rentals in the calm and protected mouth of the Saugatuck River in Westport, CT. Its beautifully designed 2 –story headquarters is a familiar local landmark at Westport’s Longshore Club Park.

Longshore Sailing School began in 1960 as a modest boating safety program for juniors run by town volunteers. It soon added dinghy sailing instruction to its curriculum and by 1968 it had become prominent throughout the country as a model public-access sailing program. By 1975 it had grown too big for the Town to comfortably handle and was taken private by John Kantor, who had been its Director for 10 years prior. He gave us our current name, Longshore Sailing School.

Longshore’s “community” sailing concept is different from traditional yacht clubs in that it is open to the public. You can get a lesson or rent a sailboat, kayak, or paddle-board for an hour with no further commitment. Or, you can enroll for more extensive instruction and progress as far as you like. Longshore routinely schedules over 100 courses each season and enrolls thousands of enthusiastic students.

Our highly refined, time-honored Core Curriculum – a sequence of courses designed to develop skills from beginner through advanced levels - is a unique part of the school and something we are very proud of. Each course comes with its own student manual, and together they provide a comprehensive sailing education when combined with our hands-on sailing drills. The Junior Program, has maintained high standards throughout its history because of its standardized curriculum and well-trained US Sailing certified instructional staff.