Jester Challenge 2026
This year was the 20th anniversary of the first Jester Challenge in 2006, and we were privileged to welcome guests from that inaugural event to Mayflower Marina in Plymouth to support the 2026 challengers at the start.
Trevor Leek (owner of Jester and a participant in both 2006 and 2010) and his wife Sandra joined us for the Skippers Dinner, along with Tony Head (also a participant in 2006 and 2010). Eric Andlauer (who arrived at Newport first in 2006 – very first successful Jester Challenger) sailed Mingming, Roger Taylor’s famous junk-rigged Corribee, across the Channel for the occasion.
John Apps (RAVEN), a participant in 2006, 2010, 2018 and 2022 joined three other Challengers at the start. His passage to Newport, despite significant sail problems and adverse weather, inspired many watchers. His track and log are on the website and will shortly be joined by an article he has written, so we leave more detail to John’s own account. Many of us held our breath for longer than is healthy, and John’s determination made our anniversary year even more memorable. (Please also read other news, below)
John was the only finisher this year, and he received the usual warm welcome and help from the NYC. As usual we are grateful to Norm and his colleagues.
The other challengers, Bob Turner, Hugh Davies and Pete Matthews, were well prepared and have their own stories to tell. For the first week of the challenge the wind stayed in the north, and all made good progress, but fast is not necessarily comfortable and skippers reported confused and sometimes rough and breaking seas. Bob suffered equipment failure and retired after a week; Hugh and Pete reached the Azores before deciding to retire.
Jester Baltimore Challenge 2027
Next year will follow the usual pattern with a challenge from Plymouth or Pwllheli to Baltimore in the Republic of Ireland, starting on 13th June. The pirates’ festival seems to have paused but we are always assured of a good welcome. A mixture of old and new faces have already registered their interest, so we expect the usual large, convivial, fleet.
There is always room for more, so register your interest via the website if you would like join us.
Jester Azores Challenge 2028
We are often asked for the date of future challengers. We plan to start the Jester Azores Challenge from Plymouth on 4 June 2028, subject to coordinating with other events at the Marina and the harbour. We already have a few skippers who are thinking ahead and have registered their interest.
Other News
Yachting Award?
We hear from the Medway Cruising Club that John Apps has been nominated for the British Yachting Sailor of the Year for his achieving in the Jester Challenge. These awards are decided by vote; if you would like to vote for John you can do so before the 7th November at:
https://www.britishyachtingawards.com/john-apps
Jester Dinner and Seminar
Following the two-day seminar at Letchworth Garden City earlier this year, a second event is planned for the weekend of January 23–24 2027. After feedback from the previous event the organisers hope to allow more time for informal discussion and aim to design the program with Baltimore challengers in mind.
If you are interested and have not heard directly from the organisers let us know and we’ll pass on your email.
One small boat
We do not advertise boats, but sometimes there has to be an exception. Sadly, due to deteriorating health, Len Hiley will need to find a home for EMU, his 1974 Hurley 27. Len’s help has been well received by many Jesters over the years, EMU reached the Azores in 2018 and Len’s video on self-steering without a windvane is on the Jester Website. If you want to know more please email the helm and we’ll pass on more details.
