Living , Modern




Snapshot of Accomplishments:
• Circumnavigated the globe five times, most of the time sailing solo:
1975–76 EGREGIOUS. San Diego, California. East via
Cape Horn and Southern Ocean. Two stops:
Auckland, New Zealand; Papeete, Tahiti.

Nuku Hiva, Marquesas Islands. West via Suez and
Panama Canals.

1984–1990 RESURGAM. Nuku Hiva, Marquesas Islands. West via
Panama Canal and Cape of Good Hope.

1991–2003 RESURGAM and THE HAWKE OF TUONELA. Sydney,
Australia. East via Cape Horn and Cape of Good

2008–2009 THE HAWKE OF TUONELA. Opua, New Zealand.
West via northern Australia, Cape of Good Hope
and Panama Canal.

• In 1975, became the first American to solo around Cape Horn
• At one point set a world record for the longest voyage in an open boat, the 18 ft. Drascombe Lugger Chidiock Tichborne
His original name was Webb Tedford. He was born on November 11, 1941 in Saint Louis, Missouri. In 1949, when he was 8 years old, Webb’s father committed suicide, and a year later the boy was adopted by his stepfather and his name was changed to Chiles.
In 1963 Webb Chiles graduated college and moved to California where he developed his writing while working at various jobs. In January 1967 he bought his first boat – a 26’ Excalibur sloop and two years later a second one, a 35’ Ericson 35 sloop, which he named Egregious. In September of 1973 he purchased a new bigger engineless boat, an Ericson 37′ cutter, which he also named Egregious.
He lived on his boats and taught himself how to sail and navigate. He made a couple of five hundred mile long passages along the Californian and Mexican coastlines and eventually felt experienced enough to take on Cape Horn. In November 2, 1974 he sailed from San Diego, California for his first attempted solo circumnavigation via Cape Horn. The sea and solitude were new to him, but technically he felt that to be a good sailor, one must accept that nobody knows the sea until one makes long passages offshore and that nobody knows solitude until spending months, if not years, alone.
Almost forty years later, Webb Chiles has circumnavigated the globe 5 times, published seven books and scores of magazine articles, and established himself as an “adventurer” in the truest sense of the word.
-Heavily paraphrased from an article in Latitude 38

Anecdote: following is an excerpt from Webb Chiles’s website :
Twice in my life I have lost everything. Once the loss occurred over a period of years while I was sailing CHIDIOCK TICHBORNE, an 18’ open boat, west around the world. When I was falsely imprisoned as a spy in Saudi Arabia in 1982, I did not own a single object, not a teaspoon or a tee-shirt, that I had owned when I sailed from San Diego, California, in 1978. The second loss was as complete but took place during a single night in 1992 when I sank the 36’ sloop, RESURGAM, off the coast of Florida, following which I floated and swam for 26 hours and was carried more than 125 miles by the Gulf Stream before reaching an anchored fishing vessel.

  • Filter Nominees

  • Reset

Preserving America’s Sailing Legacy

Engaging Sailing’s Next Generation

Stay Connected to the National Sailing Hall of Fame