Webb Chiles

OCC Jester Award - 2014

For his singlehanded passage in a Moore 24 from San Diego to Opua, New Zealand in the spirit of the Jester Challenge.

Webb Chiles, 73, was born in Saint Louis, Missouri, far from the sea and into a family where no one had ever owned a boat. In his early teens he decided he wanted to sail the world and write about it. As an adult he has: five circumnavigations—he is now on his sixth; seven books; and hundreds of magazine and newspaper articles.

He began what, time and chance permitting, will become his sixth circumnavigation, from San Diego, California in May, 2014, aboard an ultra-light Moore 24 named GANNET, and reached Opua, New Zealand four months and four stops later. Moore 24s have often been raced single and double-handed from California to Hawaii, but GANNET is the first to cross the Pacific.

Chiles calls himself an artist. One of his best known lines is: a sailor is an artist whose medium is the wind. He has written that the artist’s defining responsibility is to go to the edge of human experience and send back reports. That is what he continues to try to do.

For more information see his website: