The Jester Challenge to Newport, Rhode Island, 2026
Start off western end of Plymouth Breakwater, 1200 Sunday 10 May 2026.
Finish at a line extending due west (true) from Castle Hill Lighthouse on Newport Neck, Rhode Island.
Norm Bailey and the NYC are looking forward to welcoming Jesters to Rhode Island, and we will again enjoy the support of Mayflower Marina at the start.
Event Tracking
Challengers
| Skipper | Yacht | Type | LOA | Finish |
| Bob Turner | ONE DAY | Westerly Tempest | 30′ 7″ | Retired |
| Hugh Davies | EDEN MARINDIN EM | Vertue 2 | 25′ | Retired |
| Pete Matthews | WINGDING | Contessa 32 | 32′ | Retired |
| John Apps | RAVEN | Rival 34 | 34′ | 24/07/2026 20:30 |
Bob Turner and ‘One Day’ (Photos: George Arnison)
Hugh Davies and ‘Eden Marindin’ (Photos: George Arnison)
Pete Matthews and ‘Wingding’ (Photos: George Arnison)
John Apps and ‘Raven‘ (Photos: George Arnison)
The Start
This is the 20th anniversary of the first Jester Challenge in 2006, and we were privileged to have some VIP guests from that inaugural event come to Mayflower Marina in Plymouth to support the 2026 entrants and be part of the Start.
Trevor Leek (owner of the famous Jester and a participant in both 2006 and 20010) and his wife Sandra joined us for the Skippers Dinner in Jolly Jacks, along with Tony Head (also a participant in both 2006 and 2010). Eric Andlauer (who arrived in Newport first in 2006 – so will forever be the very first successful Jester) sailed Mingming (Roger Taylor’s famous boat) across the Channel for a flying visit – but couldn’t be persuaded to keep going on this occasion. And John Apps – a participant in 2006 (and 2010, 2018 & 2022) still going strong as an entrant in 2026.
The 2026 Jester Challenge started on a sunny but breezy day in Plymouth with all four entrants crossing the starting line in good order and cheered on by a number of supporting boats. Conditions were ideal with a blustery F5 NE wind giving the entrants a flying start out of Plymouth Sound and towards the Lizard.
Some of the supporting boats at the Start: Clockwise from top left – Mingming; Sula ; Rouselle; Cara; Island Star (Committee/Media boat);Triple Venture (Photos: George Arnison)
Sitreps
17 May 2026, Sitrep 1
The four Challengers cleared Western Approaches in one day and all have maintained average daily runs of over 100nm, thanks to wind that stayed in the northern sector. EDEN MARINDIN, WINGDING and RAVEN have followed similar courses to the South, at times their tracks are so close they would have been able to make VHF contact.
Fast sailing, however, did not always mean comfortable. Skippers reported confused and sometimes rough and breaking seas, finding themselves between a low over Portugal and a high in the Atlantic. ONE DAY (Bob Turner) suffered equipment failure and, consequently, Bob has now retired from the challenge. As we write he is heading north in the Irish sea toward home.
The weather pattern of the last week is not set to continue. Low pressures will dominate the next week. As the wind backs skippers will need to plan ahead: will they now tack west or try to get into light winds south on the edge of the Azores high?
28 May 2026, Sitrep 2.
After the excellent first week, the next provided the challengers with few options but to head west in weather that ranged from light winds and fog to force 8. EDEN MARINDIN and WINGDING have now made port in Terceira, WINGDING having to anchor outside the marina at the south end of the harbour to wait out a gale at the same time that RAVEN to the east of the Island was forced north, and has subsequently had to lie ahull through a second gale.
Hugh Davies (EDEN MARINDIN) and Pete Matthews (WINGDING) have now retired from the challenge. In Pete’s case it is sad that that primary reason is that despite ongoing efforts he failed to get transatlantic insurance cover, an ongoing problem for corithian sailors. We are sure that the three who retired are disappointed, but they have all made seamanlike decisions and made port in good order under sail. They will certainly have stories to tell and experiences to share.
When the weather permits, we expect RAVEN to head into Praia da Vitória. John has mentioned several times that he has a furling gear issue and that he may need still water to fix the problem. A brief stop may also prove convenient in weather terms, since the Azores high appears to be moving slightly north, which may provide some relief from the current train of low pressures.
8 June 2026, Sitrep3.
The last week was challenging for John Apps (RAVEN), after trying to make for calm waters in Praia harbour with a SW’ly gale blowing, John settled for Lajes harbour on Flores. Pointing has been a problem for John with his genoa out of service due to a furler problem. Once in the calm of the harbour John has repaired his furler and changed genoas and is on his way west again.
Hugh Davies (EDEN MARINDIN) is planning to stay in the Azores for a while to explore the area and Pete Matthews (WINGDING) is expected to start heading back next week.
The Azores high appears to be returning to its normal state but there is still plenty of weather for John to contend with.
On the 3rd June John reminded us that this was the anniversary of the first Jester start, 20 years ago. There is also an excellent article in the current Practical Boat Owner exploring the Jester Challenge and its history by the founder of the challenge, Ewen Southby-Tailyour, and PBO’s Jake Kavanagh.
23 June 2026, Sitrep4.
Few Jester Challengers have managed to make it as far West as John is onboard Raven in a JC event. Of those that have, most have finished. John has had a mixture of winds but very little easterly. He is now 1,400 nm from the finish but the North Atlantic drift is increasing as he approaches the Gulf Stream and the weather will undoubtedly have a few surprises to come.
Wingding (Pete Matthews) is back in the UK and Eden Marindin (Hugh Davies) continues his stay in the Azores.
9 July 2026, Sitrep5.
With only John in the Challenge there isn’t a great deal to report. John is ‘trekking’ on with a damaged main sail after a period of calm resulted in it flogging a seam loose, reminding us that light winds can take a toll on sails as well as patience. Raven has less than 500 nm to go to Newport but with the strongest section of the gulf stream to cross and changeable weather expected it is far from clear where and when John will make landfall.
25 July 2026, Sitrep6
This Jester Challenge finished when Raven crossed the finish line on 24th July 2026.
After John and Raven made it across the Gulf Stream the Atlantic had another sting in the tail when they encountered a complex weather system with periods of gale force winds. Then, whilst making his final approach he went to start his engine and it suffered a problem which John thinks was sediment that had been stirred up in the tank.
Upon crossing the line John made contact with New York Yacht Club and through a variety of message relays a VHF connection was established. They sent out a boat crewed by the commodore, vice commodore and a club officer who found Raven about 4nm from Newport off Brenton Point. They towed him in to Newport Harbour and to a slip at their club. The club manager ensured that John and Raven were taken care of and Norm Bailey assisted with organising communications and operations despite being on a cruise in the Bay of Biscay. Our thanks go to everyone involved at NYC for helping John.
John writes: “I passed Castle Hill Light at 2030 on 24 July 2026. Just thought for the record it might be interesting. I make it 75 days. Newport YC once again have been incredibly good. Hailey was on the radio every hour checking my progress in often at half a knot, although at the end I achieved 3 knots. The launch picked me up and towed into Newport Harbour.”
This has been a significant test of John’s superb seamanship, managing his boat to reach the finish line with sail problems and considerable weather challenges throughout.
Bravo Zulu John and Raven.
