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About Winston & Cynthia

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Winston and Cynthia transformed their desire to simplify their lives and be free of all their “stuff” into a mutual second career in paradise, as crew on megayachts.  

You are lead through your lifetime by the inner learning creature, the playful spiritual being that is your real self.

—Richard Bach

Cynthia, a public relations professional from the Midwest and Winston, a construction company owner from New Brunswick, Canada, met on the beach in 1990 in La Jolla, CA. Lured by an ad they saw vacationing in the Caribbean, they traded their ocean-side condo for a grass hut, running a pirate bar on a tiny island—then moved to U.S. Virgin Island’s Hassel Island, where they raised the population to a whopping nine. 


Acquiring dual U.S. Coast Guard Captain’s Licenses and transitioning from island landlubbers to fulltime professional yacht captains, Winston and Cynthia have crewed luxury sailing and motor yachts in the South Pacific, Pacific, Atlantic, Caribbean, Gulf of Mexico, and the Intracoastal Waterway.  They’ve hosted more than 100 week-long yacht charters and are well-known throughout the industry, having worked in it now for almost twenty years.


'Great fun read guys!' - Tim E

"An Exciting Must Read!" -  Jim White

"Inspiring & Delightful "- Suzanne L

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