Wayward circumnavigator

Kevin Green | VOLUME 31, ISSUE 3
While many men in their 70s are putting on their slippers, 74-year-old American sailor Webb Chiles is sailing over the horizon on his sixth circumnavigation
Webb Chiles has been shipwrecked, swamped and cast ashore on remote islands, but still can’t imagine life off the water.

A lifetime of near-continuously sailing the world’s oceans has again brought the legendary Webb Chiles near our Australian shores. I thought it prudent to invite the 74-year-old American for a Cheeseburger in Paradise, as singer Jimmy Buffet would say. But alas, for his sixth circumnavigation, Chiles is crossing the Tasman Sea north of Sydney.

“I really enjoyed sitting on my mooring in Elizabeth Bay, but this time I’m hoping to make landfall in Bundaberg,” he emailed from his mooring in New Zealand.

Ignoring the mantra of a sailing boat’s length matching your age, Chiles’s boats have become smaller during his five decades of sailing (the current boat is a lightweight 24ft Moore).

Chiles has ticked a number of items off his bucket list, including being the first solo American sailor to round Cape Horn in his relatively small Ericson 37, in 1975, and breaking Englishman Sir Francis Chichester’s 1966 solo round-the-world record. In rounding Cape Horn, he beat Joshua Slocum on a technicality, as Slocum took the Strait of Magellan shortcut, rather than rounding the outer Horn Island. Chiles was capsized three times in the Southern Ocean and, despite a cracked hull, continued on to round Cape Horn.


I first heard of Webb Chiles while reading his book The Ocean Awaits, an account of his world voyage, from 1978 to ’84, in a tiny open boat, the 18ft Drascombe lugger Chidiock Tichborne I. In the book, Chiles describes buying the fibreglass Drascombe using all his money – $5000.

“I stopped working for other people in 1974. I also stopped being in debt then. Debts are chains,” says Chiles. “I have no credit rating because I haven’t borrowed money since 1973. I pay cash for everything, including my boats. If I don’t have cash, I don’t buy.”

His humour is evident throughout his life and in his books. Of the 16th-century poet Chidiock Tichborne, who inspired the boat’s name, he says: “Fitting a 19ft name on an 18ft foot boat was an amusing early challenge for the six-year voyage.”

Starting that voyage in 1978, he hoisted Chidiock Tichborne I’s red sails on the yawl rig and sailed away from San Diego. Many, including his recently divorced fifth wife Suzanne, thought they’d never hear from him again. Chiles nearly proved them right when the lugger was swamped between Fiji and Vanuatu, causing him to drift 300nm alongside the sunken hull in his rubber dinghy.

“Almost dying is a hard way to make a living, I once wrote. I have been in force 12 storms at least eight times and almost died yearly for decades. Due to strength and intelligence, I immodestly claim, and time and chance, I have survived,” Chiles says.

After recovering in Vanuatu, he went on to make a record-breaking open-boat voyage of 4058nm from Singapore to Aden, Yemen.

Chance is something Chiles knows well from many near scrapes. Having chanced a landing in Saudi Arabia, unannounced, he was jailed. While he was lucky to be released, his boat never was. But, keen to reap the publicity benefits, the English Drascombe company supplied Chiles with a replacement boat, Chidiock Tichborne II, which enabled him to continue the circumnavigation – until he halted inexplicably in the Canary Islands after 25,000nm.

“I made the voyage to please myself, and I stopped for the same reason. I had started the voyage to sail to the edge of human experience, to explore the unknown, to try to do what some people considered to be impossible. After five years and 25,000nm, that edge of experience had been charted, that unknown had become known, that impossible proved possible. I had nothing more to learn from it, and I was no longer willing to subordinate everything in my life to it,” Chiles wrote in the epilogue of The Ocean Awaits.


At the top of the affable American’s list of favourite places is the southern hemisphere. While discussing his upcoming Tasman crossing, I suggested a favourite place of mine, Lord Howe Island, which happens to be high on his list. The lagoon is a welcome spot after a long tack from Sydney and is a real paradise. For Chiles, who has sailed many sea miles, there are surprisingly few top spots. New Zealand is one, which was also the home of his fifth wife.

“I first sailed into New Zealand 40 years ago and have spent more time there than in any country other than my own. I’ve also spent more than three years in Australia,” he says.

Of Chiles’s colourful marital history, I’d venture to say the sea is the mistress he ran away to. He has, however, been happily married to Carol for 21 years. He also sailed with his previous wife, Jill, aboard the She 36 Resurgam on a circumnavigation that included a second rounding of Cape Horn.

“Certainly, my sailing has impacted some of my marriages. That the numbers of marriages and circumnavigations will be the same, if I successfully complete this one, is chance,” he says.

Resurgam proved to be an accident-prone yacht, colliding with a ship off the Bahamas and nearly losing the mast.

“A grating, twanging sound. Metal to metal. Harsh. A giant file rasps the strings of a giant guitar. This is it, Jill,” he wrote in his book, Single Wave, of the collision and fear of imminent shipwreck.

Despite surviving yet another near sinking, disaster followed for his relationship and the ill-fated Resurgam when, in a fit of despair, he scuttled her off Florida, thus ending a nine-year relationship with his favourite yacht.

“I was Socrates after drinking hemlock,” he wrote afterwards.

From the sinking yacht, he swam in the open ocean to his expected death.

“I had wanted her to be my last boat and Jill to be my last woman. Now, both were.”

Despite staring death in the face, he wouldn’t succumb. Chiles floated and swam, with his life story unfolding in his confused mind, until he was rescued after 26 hours. The jaded and wounded sailor stumbled on land for a year until the pull of the sea grew again. At the end of the same year, Chiles owned a 37ft IOR yacht The Hawke of Tuonela. Sailing into Key West some months later, he met Carol, who went on to sail 10,000nm with him during his fourth circumnavigation.


For those who have used a sextant (I have difficulty getting sights even from a large, stable yacht) the idea of relying on one in a small boat surrounded by islands and reefs is inconceivable. Yet this is how Webb Chiles navigated until the advent of GPS in 1995.

“I’m pleased to know how to navigate with methods that have not changed much since Captain Cook’s day. Knowing your position within a probability of five miles seems outrageous today, but five miles on most boats is less than an extra hour of being alert,” he says.

He had used the precursor to GPS, SatNav, on Resurgam, but the irregular updates caused him endless worry, as did another unusual item for his boats – a diesel engine. During that trip, he often used the archaic, but effective, Radio Direction Finder to beam into major beacons, such as while battling through the infamous Agulhas Current to Durban Harbour, South Africa.

These days, Chiles embraces technology, using an iPad mini as his chartplotter, with the iPhone iNavX app as a backup, plus a laptop. The laptop is connected to a Garmin eTrex GPS unit, which he uses in his current boat’s cramped confines.

Bought for $9000 in 2011, the fin-keeled Moore 24, Gannet, has a flush deck, which prevents its skipper from sitting upright below on the benches, so Chiles rests on the floor. The yacht’s reputation for toughness, despite the light build, attracted Chiles. He has made several modifications, including a carbon bowsprit, a tiller and – to help run the small tillerpilot – solar panels. Interestingly, he uses an electric Torqeedo outboard, which powers both the yacht and its tender. He named the yacht Gannet after the ocean bird he admires for its grace.


Chiles has completed five circumnavigations, a feat surpassed only by Japanese solo yachtsman Minoru SaitM, who finished his eighth at 77 years of age. Now completing his sixth, I put it to Chiles that there can’t be much left on his bucket list.

“The simple answer is: no. But I still refine my experience, always trying to simplify, to find the easiest way to do things. I don’t claim to know it all, or that my way is the only way,” he says.

Preparing his body as well as the boat is a key factor, says Chiles, who does as many press-ups as his age – 74 years – and walks a lot when ashore. At sea, he’s an unfussy eater and is using freeze-dried food from Back Country Cuisine, New Zealand, on his current voyage.

He has also a more leisurely pace, flying home to Chicago from his mooring in New Zealand and then returning to enjoy the Bay of Islands while preparing for the Tasman Sea crossing, a waterway he knows well.

Subtropical Australia is his next port of call, possibly Bundaberg, if the weather permits.

Chiles and I do have one thing in common – he likes the strong malts of my homeland in the Scottish Highlands, with 10-year-old Laphroaig his regular tipple aboard. Finishing our correspondence, he quotes his mission statement, which really says everything about this extraordinary sailor: “Live passionately even if it kills you, because something is going to kill you anyway.”