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Jester Challenge a tribute to self-reliance

Fifty years after the first OSTAR single-handed trans-Atlantic race, the third Jester Challenge for single-handed sailboats 20 to 30 feet gets under way May 23 from Plymouth, England, to Newport, R.I. As of early January, 93 solo sailors had registered.

"The Jester Challenge - a continuing experiment in old-fashioned self-reliance, self-sufficiency and personal responsibility - encourages oceanic passages in small boats sailed by independent yachtsmen exercising their individual freedoms at sea," organizer Ewen Southby-Tailyour writes about the challenge.

The challenge will be thoroughly Corinthian, without any sponsorships or fees or organizing authority or rules, for that matter - only "those governing common sense and good seamanship," intones Southby-Tailyour, biographer of Blondie Hasler. Hasler was the first owner of the original Jester, a 25-foot bluewater solo sailer, and a co-founder in 1960 of the OSTAR.

"No skipper is likely to enlist onshore navigational and meteorological help and there is no time limit," writes Southby-Tailyour. "Without inspections, the Jester Challengers will sail against each other on an individual basis and ... are not expected to give a fig about level playing fields, but are expected to 'behave like gentlemen' over numbers on board and the use of an engine.

"The skippers will be happy once again, I trust, simply to reach their destination safely, take their own finishing times and then compare rigs, routes, equipment, clothing and diets. In the early days, some suggested we insist on oil lamps, towed logs and sextants, but while the Jester Challenge is for small vessels - some of whom may well have been built in pre-GPS days - there is nothing Luddite about it," he writes. "Satellite navigation will continue to predominate, as will - unsurprisingly - wind vanes. With no regulations, Jester Challengers can carry - or not carry - what safety equipment they like, based on personal experience: We rely on the maturity of the skippers."

Southby-Tailyour says the event flies in the face of rampant professionalism and hyper-competition in sailing, and a surfeit of "nautical nannying" that assumes that small sailboats skippered by skilled seamen are not seaworthy.

"The begrudgers might note, too, that the Jester Challenge continues to fill a gap demanded by traditional and proper seamen who would otherwise be denied the opportunity to pit their wits against both the oceans and other like-minded seafarers," he concludes.

Information is available at

See related article:

- Gentleman sailor, master navigator

This article originally appeared in the March 2010 issue.