Seascape The Webb Chiles Interview

We caught up with famed sailor and author Webb Chiles just after he’d finished his sixth circumnavigation at age 77.

Webb’s long list of exploits are well known, including his harrowing Pacfiic crossing aboard an open 19-foot Drascombe Lugger called Chidiock Tichborne. There might not be anyone alive with as many small-boat sea miles and stories as Chiles—so naturally we had plenty of questions for him.—Eds

When did it all start—your love of boats and sailing and then especially the thirst for adventure?

First, I do not love boats, as some seem to, and I do not thirst for adventure.

I have great admiration for some boats, particularly small ones that if well designed, well built and well sailed can do so much more than most think possible, but I do not love them. Long ago I learned not to love anything or anyone who could not love me back, and while I believe that boats, along with musical instruments made of wood, seem more alive than any other of man’s creations, they are not.

Of adventure, I have said that amateurs seek adventures, professionals seek to avoid them. I have lived this long and sailed so far only because I plan, prepare to the extent of my resources, never do anything at the last minute, and though I have taken risks, I have never taken an uncalculated risk.

Having said that, my desire to sail oceans came from my childhood spent in a suburb of Saint Louis, Missouri, about as far from the ocean as one can be. I was an only child and not close to my mother and stepfather and I did not want to be there. So I escaped as many do through books. I read Slocum and Conrad and Irving Johnson’s articles in National Geographic about his circumnavigating with paying crew in the brigantine Yankee.