The Jester Challenge 2006


New member
10 Mar 2005

The first single-handed trans-Atlantic Jester Challenge for yachts under 30 feet LOA will start at the end of May 2006 from a line off Plymouth and finish at Newport, Rhode Island. The Jester Challenge will be held every four years thereafter: there are no entrance fees, inspections, time-keepers or (formal) prizes.

The object of The Jester Challenge is to further the spirit of long distance, single-handed sailing in small boats, purely for sport and the camaraderie of other competitors. It will also pay tribute to 'Blondie' Hasler, the originator of the Single-handed trans-Atlantic Race, inventor of the servo-pendulum self-steering gear and designer of Jester. This 25 foot Folkboat-style, junk-rigged yacht has competed in every OSTAR since the first in 1960 but from which she has now been disenfranchised due to her size.

The second Jester Challenge will take place in 2010 on the 50th anniversary of the first race in 1960 when five yachts started and five finished: four of these were under 26 feet. It is expected that in 2006 at least two of the original competing yachts - and possible all five - will take part for it is hoped to invite Gypsy Moth III. Jester herself is the first confirmed entrant.

There are just two rules and one recommendation:

Competing boats must be 30ft LOA or below (unless invited by a majority of the other skippers)

It will be the responsibility of the skipper/owner to ensure that his/her vessel is covered by third-party insurance up to £2 million and

It is recommended that competitors sail a single-handed, open sea passage of 500 miles before the start in the vessel in which they intend taking up The Jester Challenge.

This is not a Race in the accepted meaning of the word and thus The Jester Challenge is, emphatically, not in competition with the Royal Western Yacht Club's OSTAR: a race for larger yachts and held in different years.

The Jester Challenge exists on the understanding that everyone has the right to sail across the Atlantic single-handed and 'in company' without submitting themselves to rules and regulations other than common sense, good seamanship and the established COLREGS: thus there are no sponsors, no organisers, no committees, no one responsible for collective or individual safety and no one has a duty of care to the competitors other than the skippers to themselves. Skippers will, individually, be expected to inform the appropriate authorities of their intended passage as they might - or might not - for any other lengthy or oceanic cruise.

For further information about The Jester Challenge please email the co-ordinator through If anyone knows the whereabouts of Cardinal Vertue, would they also e-mail the co-ordinator.


25 Nov 2004
Wortham, Suffolk, UK
How absolutely fantastic!

I wonder if we can expect to see any of the three intrepid stalwart East Coast OGA Vertues compete, after their limbering up passage to the Azores and back this year. The Jester Challenge appears to be formulated with a similar thought process and ethos to their own trip.

I hope it is a huge success, and if the challenge comprises a majority of classic boats, perhaps this forum could get together a fleet to send them off in style.

Thank heavens my boat is 31' LOD so I've got an excuse.


30 Nov 2002
I agree.

37ft, so an even better excuse.

Mind you, she is a close relation of Gipsy Moth II...


New member
3 Jan 2004
cked up for Aggrivated Arson
Me too.

I'm saved by a mere 6" (although LOA, measured last weekend for the first time, is 38' from bowsprit to mizzenboom). Might well be interested in forming part of a send-off fleet, though...

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