So you set off sailing and eventually get back to where you started from. This latest loop took Chiles many years, with many trips back to the States between legs. You can read all his reflections over the past 6, 7? years of Cruising World. It's not as if he's going so as to be the fastest, youngest, oldest, most-times-married. It's just what he does, like some people make the donuts every morning.