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A Sailor for Life

Assembling the Puzzle: Dennis Caprio's quest to "find himself" in 1970 led him to discover sailing. Mission accomplished.

Dennis Caprio sailing

Early in September of 1970, I overloaded my 1967 BMW R60 motorcycle and set off on a ride-about—same as the Australian walk-about but less tiring. I was 26 and wanted to find myself. Among the tangibles I’d need to sustain the search, I carried a Kodak Retina III 35-millimeter camera and a small bag of Tri-X black & white film, a Royal typewriter, paper, a two-man tent, sleeping bag, single-burner camp stove, a kit of nesting pots and pans, a coffee pot and a duffle full of clothing. I reckoned that observation and introspection would guide me to the elusive self. Decades later, I continue to search for my “self,” but—older and wiser now—I know it changes configuration and theme more rapidly than I can discover relevant pieces.

Still, I have to credit a stop on my ride-about year for leading me to the first and most significant shape in the puzzle. Visiting friends in Painesville, Ohio, I learned to sail! — at night, aboard a 32-foot wooden sloop of unknown design, build and age. When Jake, the boat’s owner, suggested that I steer, we were close reaching on starboard tack under genoa and full main. Jake advised me to watch the wool telltales on the windward shroud and keep them flying at about a 45-degree angle. I couldn’t see them well enough to discern an angle, so I relied on the feel of the tiller, loading up in the puffs and going slightly soft in the lulls, to keep the little boat on course. When I sailed too close to the wind, I could hear the sails luff and feel the steering go limp. If I steered too low, the tiller felt numb and the boat slowed.

We sailed until dawn, and when I climbed onto my motorcycle a day later to head east, my life had changed. I was a sailor and would be one forever.

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