Webb’s Done It Again

Legendary cruiser Webb Chiles marks a birthday with yet another cruising adventure. "Editor's Log" for our September 2009 issue.

August 19, 2009

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Marianne Lee

For as long as I can remember, it seems like I’ve been reading sea stories by Webb Chiles. Not a story every night, mind you. But steadily, over the years, his have been among the tales that have stood out from the mainstream, often hauntingly so. Webb’s been at it a long time. He first set sail in 1974 from San Diego, California, aboard Egregious, bound for Cape Horn.

Twice denied a rounding in a boat battered and broken, he returned again, and on this third try became the first American solo sailor to dip into the Roaring 40s and sail around the southern tip of the continent. From there, he continued eastward through gales, knockdowns, and equipment disasters to complete a two-stop circumnavigation in what was then the fastest time recorded in a monohull. It’d taken him 348 days, 202 of them spent sailing.

His stories from that trip, including the narrative of his first book, “Storm Passage: Alone Around Cape Horn”, would clearly indicate that Webb marches not to a different drummer but to his own drum and bugle corps, for which he’s written the music and composed the choreography for a wild, driving dance with the sea. If there’s any doubt, dear reader, well, read on, through his later works and the accounts of his next three circumnavigations; one was undertaken in an 18-foot open boat, Chidiock Tichborne, and none of them went strictly according to plan. Or perhaps they did. While others might take to the sea in search of tropical sunsets and memorable landfalls, Webb’s stories have all been about pushing the limits-his limits.


Or as he says near the end of “Storm Passage”, as he ponders a second circumnavigation: “There will be other commitments and other voyages for me, including another solo rounding of Cape Horn-after all, who, having visited hell, would not, given the opportunity, return to see if it really was as bad as he remembered.”
After the end of his fourth great circle, in Sydney, Australia, in 2003, The Hawk of Tuonela and Webb ended up on a mooring in New Zealand’s Bay of Islands. For the next few years, he’d return from his Stateside home to sail seasonally to distant Pacific islands in the way that many weekend warriors might take an overnighter to an anchorage just down the coast. Then, in 2008, he set out again to sail around the globe, first to South Africa, where he left the boat briefly, then on across the Atlantic, through the Caribbean and the Panama Canal, and back across the Pacific.

Earlier this summer, Webb wrote from Nuku Hiva, in the Marquesas Islands, where he’d stopped to rest and to consider making repairs. A strand in a windward shroud had parted several hundred miles east of there, but he’d rigged lines to the lower spreader so he could push on and make his landfall. After lying in a rolly anchorage in the Baie de Taiohae, he concluded that it’d be safer to sail on “conservatively” with the jury rig and cover the 800 miles to Raiatea than to try and make repairs then and there.

And that’s what he did. He sailed through the pass at Raiatea a couple of weeks later with the mast still standing to technically complete his fifth circumnavigation; he’d sailed there earlier from New Zealand on one of his seasonal forays. The time at sea: 169 days. This fall, as he closes in on his 68th birthday, he plans to return and sail the 2,200 miles to his mooring in the Bay of Islands. If there are no disasters, and he can do it in less than 32 days, he’ll beat the point-to-point record he set in Egregious 34 years ago.


In another note he writes, “While this will be far from a world record now, it’s pleasant to consider setting a personal best in my old age.”

And if he does, you can bet there’ll be another grand sea story to tell.
I can’t wait to read if-and how-he makes it.

Mark Pillsbury


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