JOHN "sean" BOLEBRUCH

Sean moved to Rockaway in 2009 hoping to foster a deeper connection with water. At first it was the ocean which drew him, but soon enough the bay began to whisper.

From 2012 to 2017 he managed and maintained the fleet of wooden fishing skiffs at Marina 59. Around the same time he acquired a Seidelman 37 sloop that was sailed locally for fun, without an engine no less; thereby putting his true sailing skills to the test. Since then he's twice circumnavigated his Norfolk Oyster sailboat  around the entirety of Long Island.

Sean grew up in Port Washington NY, located on the north shore of Long Island. Port Washington boasts a strong boating community and a lively harbor known as Manhasset Bay. His experience in boating began at a young age when his father John Sr. propped him up at the helm. Many childhood summers were spent bopping around in dinghies or on extended voyages aboard the families Herreshoff cat ketch 31 "Splash".

Over the next three decades, the continual pursuit of sailing would lead Sean on many journeys throughout New England, the Caribbean, Mediterranean and especially right here in his own backyard of New York.

Captain Sean is an American Sailing Association Certified Instructor with credentials in ASA 101, 102, 103, and 104; with more to come. 

Sean continues to grow Sail Rockaway to further peoples connection to the water in creative, meaningful and fun ways.

SAM JACKSON

Sam Jackson developed his sailing skills from a young age in the waters of Cape Cod, where he excelled racing Optimists and 420s.

As an instructor at Chapoquoit Yacht Club for more than a decade, Sam taught and inspired many students who have since achieved greatness as racers and mariners. After graduating from Colgate University, where he competed on the sailing team, Sam's love of classic racing sailboats led him to a job as crew aboard Nefertiti, a 1960's America's Cup racing yacht docked in Newport, RI.

In 2010, Captain Sam sailed from Hawaii to San Francisco aboard the 134 ft sailing brigantine; the SSV Robert C. Seamans, using only the sun and stars to navigate. Under the guidance of the Sea Education Association, which specializes in sail training and oceanographic research, Sam and the crew collected scientific data for UC Berkley during their oceanic voyage. After a month at sea, Sam took the helm under the Golden Gate Bridge and was later gifted the classic red beanies by a representative of the Jacques Cousteau Society. Long story short; Captain Sam is a tried and true salt. 

After moving to NYC, Sam served as Port Captain aboard the Nantucket Lightship WLV-612 in Brooklyn Bridge Park before buying his own classic sailboat, fixing it up and sailing it down the Hudson River to Jamaica Bay at Marina 59.

Sam has been a main instructor for our youth program. We sail, swim, and explore shoresides in Jamaica Bay. 

All Sail Rockaway captains are currently licensed by the United States Coast Guard for commercial passenger vessel operation. Our captains are also trained and certified in CPR/First Aid.