The magical feeling of gliding across the water in a sailboat can be a healing experience. Connecting people to the thrill of sailing and the beauty of the natural environment is our goal.

SAIL ROCKAWAY was founded in 2017 by lifelong sailor and waterman John Bolebruch. The goal is to make sailing and connecting to the water more accessible for all through diverse offerings and affordable rates. Ever expanding creativity, exploration, and education are the principles that are the foundation of Sail Rockaway.

Jamaica Bay boasts the best cruising grounds in New York City. Expansive, diverse, well protected and consistently groomed by the ocean breeze. The bay is home to a multitude of nearby wildlife preserves and parks all accessible by boat. The flagship vessel for most sailing tours and lessons is the Norfolk Oyster 17. Perfectly suited for exploring the nooks of Jamaica Bay while maintaining the comfort and safety of a much larger boat. The newest member of our fleet is the British-made Drascombe Lugger. Ours is the first Lugger ever to arrive in the United States from the UK back in 1973. We like to think that she has a certain mystique to her. We also include a Catalina Capri 22 and Optimist dinghies for classes. We have a dedicated Youth Summer Sailing program, plus a series of adult classes designed to accelerate students skills on the water. ​Catering to all skill levels and ages our present offerings are Lessons, Tours, and Youth Sailing.