John Calimafde was a self-taught sailor. He primarily competed in two one design classes.
History of the Ensign Class
by Gerald Daly (1990)
“John Calimafde, of Old Greenwich, Connecticut, is a perennial winner in his fleet and regional regattas in Ya ‘ssoo. Ensign number 101, and has placed in the top five at the national championships seven times. Sligh and Calimafde are among the many Ensign sailors who haul their boats to regattas on trailers. Doing that is not easy. It takes a staunch trailer, a larger car or small truck, and plenty of common sense, but it is done frequently and successfully.”