Ewen Southby-Tailyour once descibed it as ‘a modern experiment in old-fashioned self-reliance, self-sufficiency and personal responsibility’.
Every two years a group of singlehanded sailors heads for Plymouth to sail the Atlantic. The Challenge in 2024 will see them head off to the Azores and 2026 will likely see them making a full Atlantic crossing to Newport, Rhode Island. In the intervening odd years there is a less challenging passage to Baltimore in Ireland. The Jester Challenge is not a race in any way, shape or form, simply an opportunity for skippers to test their boats and their seagoing mettle in a supportive and non-competitive environment. Skippers can make stopovers in other ports or harbours if they so desire, and there is no stigma attached to retiring from the event. Each sailor takes full responsibility for him or herself, their boat and the equipment they carry. There no entry fees and virtually no rules, although there are guidelines.
Prognosis of future Jester Challenges (JC, JAC and JBC) with outline start dates:
- 2026 Newport 10th May
- 2027 Baltimore13th June
- 2028 Azores early/mid June
- 2029 Baltimore mid June
The background of the Jester Challenge and its ethos is described by Ewen Southby-Tailyour in a 2006 article. The first challenge was held 2006, following a meeting of potential participants at the 2005 boat show.
The co-oridination of the challenge was undertaken by Ewen, who flew the original Jester burgee throughout every Jester challenge from the starboard cross trees of Black Velvet. It was flown on Equinox for the start the 2018 challenge then transferred to Black Velvet and is flown until every Jester is safely accounted for.
In 2021 Ewen formed the Jester Helm, a small group of Jester challengers who now co-oridinate challenges.
Jester Challenge 