Webb Chiles grew up far from the ocean in a non-sailing family.  Fortunately for the sailing world, he was an avid reader and the likes of Slocum and Conrad lead him to purchase at age twenty-five his first boat, an Excaliber 26.  Less than ten years later he made his first circumnavigation in an engineless Ericson 37, with only two stops, becoming the first American to sail alone around Cape Horn and setting a then world record for the fastest solo circumnavigation in a mono-hull, breaking Sir Francis Chichester’s time by more than three weeks.  

Two years later in 1978, wanting a quantitatively different experience, Chiles set off from San Diego in Chidiock Tichbourne, an eighteen-foot undecked yawl-rigged Drascombe Lugger and made what was then by far the longest open boat voyage, of more than 20,000 miles.  His third circumnavigation and part of this fourth was made in a Sparkman & Stephen designed She 36, Resurgam.  He completed his fourth circumnavigation in a 37-foot Heritage One Ton, Hawke of Tuonela, after Resurgam sank in the Gulf Stream, and then made a fifth in the same boat.  At seventy-three, not wanting to rest on past accomplishments and again wanting a new experience, Chiles has, in his own words, set off on what, time and chance permitting, will become his sixth circumnavigation, the “new experience” being undertaken in Gannet, an ultralight Moore 24.

It is noteworthy that Chiles has made all his voyages in stock boats and never had a sponsor.  Chiles is also a survivalist.  His undecked yawl was pitchpoled and swamped in the South Atlantic, leaving Chiles to survive in a nine-foot inflatable dinghy for fourteen days before reaching land three hundred miles away unassisted.  In the Red Sea, the Saudis seized Chidiock Tichborne and imprisoned him as a spy. When Resurgam sank, he swam for twenty-six hours in the Gulf Stream before being rescued by a fishing boat.

"People who know of me at all probably do so as a sailor; but I have always thought of myself as an artist, and I believe that the artist’s defining responsibility is to go to the edge of human experience and send back reports. Here are my reports."

1974 Egregious, Ericson 37. East via Cape Horn and Good Hope. 203 days, 2 stops. No engine.

1978-1984. Chidiock Tichbourne I & II, Resurgam. 18’ Drascombe Luggers, 36’ S&S Cutter. West via Suez and Panama. (CT I seized by Saudi authorities, CT II donated by builder, resumed voyage in Egypt, then left the boat in the Canaries, resumed voyage in Resurgam).

1984-1990. Resurgam, 36’ S&S.  West via Panama and Good Hope.

1991-2003. Resurgam and Hawke of Tuonela, 37’ Morgan 1-ton sloop. East via Cape Horn and Good Hope. (Resurgam sank off Florida, Chiles drifted 30 hours in Gulf Stream, picked up by fishermen).

2008-2009. Hawke of Tuonela. West: New Zealand-Australia-Good Hope-Panama-New Zealand.

2014- 2017. Gannet, Moore 24. West. San Diego, S. Pacific-Good Hope-Marathon, FL.

(Intends to proceed to San Diego via Panama).