Gary O’Grady and Katy
‘Due to covid’ is an oft quoted phrase precluding a change to the normal run of play in any event and sadly The Jester Challenge for 2020 and 2021 were no different.
2020 should have staged the Jester Baltimore Challenge (JBC) which coincides on each occasion with Baltimore Pirates week in Southwest Cork. A fun event marking the blackest night in Baltimore’s history when the town was sacked by Barbary pirates in 1631. Usually, the Jester challengers arrive in full pirate regalia to add colour to the festivities. The 2020 Jester Baltimore was tipped in to 2021 with quite some route alternations requiring it to be renamed Jester 518.
The Jester Challenge was founded by Ewen Southby-Tailyour in 2006 as a single-handed sailing challenge (not a race) to celebrate the exploits of war hero Blondie Hasler. The challenge is restricted to boats of 20’-30’ LOA with some exceptions. The name Jester comes from the boat Blondie Hasler famously sailed in the first OSTAR race of 1960. Blondie was a firm believer in relying on oneself in times of difficulty at sea and once quipped ‘one should drown like a gentleman’ rather than seek outside assistance. The core tenants of the Jester Challenge today stem from this attitude – self-sufficiency & good seamanship.
As the JBC couldn’t visit Ireland this year a new route, and possibly even more challenging than the usual, was devised by the new ‘Jester Helm’. With Ewen stepping down this year from 15 years of indefatigable organisation and leadership in this event, it was decided that it would take a team of 3 to continue this role. Thus the ‘Jester Helm’ was formed consisting of previous and current Jester challengers Roger Taylor, George Arnison & Howard Chivers.
The challenge started in both Plymouth & Pwllheli, North Wales. The Plymouth Jesters must leave to starboard- Draystone Ledge Buoy, Bishops Rock Lighthouse and a waypoint 51 degrees north, 8 degrees west then finish off St. Anns Head at Milford Haven. The Pwllheli entrants must only leave the 518 waypoint to Port and again finish at Milford Haven. The conditions favoured the Welsh, so it was no surprise they began arriving first.
I was part of the Plymouth entry and spent a relaxing week in Mayflower Marina getting the boat ready (or should have been) and getting to know the staff rather too well in the bar/restaurant, Jolly Jacks each evening.
The entry list was as follows,
Plymouth
| Bill Churchouse | BELGEAN | Westerly 22 | 22′ |
| Bob Litton | JALINA | Sadler 25 | 25′ |
| Christopher Ling | POCKET BATTLESHIP | Django 7.70 | 25’4 |
| Chuck Dandridge | J’HANA | Sadler | 29′ |
| Gary O’Grady | KATY | Westerly Konsort | 29′ |
| John Moody | BLACK MAGIC | Mirage | 29′ |
| John O’Rourke | Nirvana | Marcon Sabre 27 | 27′ |
| Katie Long | BLUE DIAMOND | Sadler 26 | 25’10 |
| Mark Castle-Smith | ANOMALY | Bent 24 | 24′ |
| Ronald Olivier | KERRIN II | Westerly Griffon | 26′ |
| Tony Head | TRIPLE VENTURE | Twister | 28′ |
Pwllheli
| Bob Angell | COMRADES | Morecombe Prawner | 28′ |
| David Knowler | HEADWAY III | Achilles 840 | 27’8 |
| Geoff Turner | DAWN | Parker 21 | 21′ |
| Mike Lynch | BONEGI | Twister | 28′ |
| Roger Fitzgerald | ELLA TROUT | Dehler | 29′ |
Day 1
The start was midday from both locations but with little wind outside Plymouth there would be serious progress issues once the flood tide started at about 17:00. Any gains made before then could potentially be washed away with the next tide. Most entrants headed offshore but I decided wrongly to stay closer to land and I was very quickly punished with a complete no wind zone. With no wind above 3 knots for the first couple of hours the rest of the fleet disappeared very quickly over the horizon. My idea was to stay close to land with the aim of anchoring on the tide change to wait for more favourable winds.
This actually turned out to be a fortuitous decision as by early evening, myself and most of the fleet were now anchored just outside Looe but I’d only completed a fraction of the miles to get there. The 3 frontrunners of Pocket Battleship, Anomaly and Triple Venture had made more progress and reached Fowey for the night. With no wind likely til dawn at least a comfortable night could be expected.
Day 2
Tony Head in Triple Venture was very quickly out in the morning and shot off from Fowey soon disappearing from my AIS. I was off at 05:00, as were most boats, but again with light winds for the first few hours until, when a few miles from my Lizard waypoint, all of a sudden I was needing to reef and I was flying along quite merrily, relieved to be making good progress. The winds settled down to a more consistent F4 so I shook the reef out and guided Katy off to the Scillies. Always on the very edge of my AIS coverage I could see J’Hana who, almost sensing I was there, picked up her skirts and was gone again. I spoke to Chuck afterwards in Dale and this was exactly the case. After a good run he told me Katy seemed to just pop up on his screen a few miles away hot on his tail which gave him the encouragement to get going, but remember – It’s not a race!
We saw a few retirements today with boats scattered round the south Cornish ports. By the very late evening there were just 3 Plymouth Jesters left heading north towards this imaginary point 518. Tony in Triple Venture was there first always keeping well ahead of the fleet.
Passing the TCZ south of the Scillies was proving awkward with again low winds. I intended to use the inshore zone but couldn’t get the right angle on it and had to opt for full use of the west going TCZ. I entered around midnight and didn’t see another vessel all night and was finally out, past the north, south TCZ west of the Scillies and heading north just after 1000. I saw nothing of the islands themselves, just the nightime lights.
Day 3
After a long night keeping lookout ‘by sight and sound and by all available means’ it was a relief to be out in open water and away from the threat of traffic to enjoy a well-earned 20-minute nap! This is about the most you can achieve safely in these waters. There was a great and very long swell of about 4 meters I should think which was a pleasure to sail across with a very soothing motion. I managed to catch up on a bit of sleep here. The 518 waypoint was now around 70 miles away. As the day closed and we went in to evening the wind and waves started picking up as if saying, ‘you can’t ignore us – we’re here all night’. Indeed, they were. Nothing dangerous or threatening just very annoying short sharp knocks on the hull in a very successful attempt to keep me from dropping off.
My gas bottle decided to run out at 01:00 so this needed replacing if I were to maintain the regular caffeine fixes. Then at about 03:00 the batteries died, and I lost all electric. I did have a warning of this when the plotter gave an indication that the tiller pilot was running low on his usual voltage. I decided to give the batteries a boost with the engine but as soon as the engine tried to start all the electrics completely dropped and I was left in darkness with no instruments. So apparently it does happen. I was also very tired but could at least figure out to change to the starter battery which is isolated and got everything working again. I read all the batteries voltage (I have a house bank of 3) and took out the bad boy and charged up the other 2 and things were again back to normal.
However, I did get some company to perk me up. A pigeon had joined the crew and sat itself on the coach roof during the night and stayed with me until Milford Haven where I’m sure it has made new friends now. I did check if it were a racing pigeon but no tags or rings. I kept him fed and watered for the journey for which he seemed grateful. Not sure if this breaks the solo sailing rules but as he very selfishly didn’t offer any assistance I think I’m ok.
I settled down for another nap but was rudely awoken at 05:00 by the wind having a very sudden shift from SW to NW. It was as if someone had pushed a button as there was no gradual veering, but an instant change and I had some work to do to change the sails and get going again. The really annoying thing was the waypoint was now exactly where the wind was howling from. When the wind shift came in I was about 2 hours from the waypoint but it took me a torturous 7 hours to get round it adding 5 depressingly long hours to the journey. And what’s more there was Chuck and J’hana just appearing once again at the top of my screen laughing as they rounded the waypoint. I was never to see them again til the finish. This was my lowest point. In my head I was giving up sailing and selling the boat. Never has a mark been more difficult to round with the wind now blowing from all directions from F1 to F6, it was completely ludicrous. I didn’t know whether to tack, gybe, reef, kick the pigeon but instead opted for more coffee. Tiredness was taking its toll.
Day 4
After finally rounding the mark after midday I set course for the final run home many many miles away and collapsed in a heap.
The night was spent reefed down as I was beginning to really feel exhausted now and didn’t want any sudden surprises in the night to deal with. I just needed Katy to take over completely which she did admirably. I tried to sleep but every noise on board seemed to be otherworldly and I began sound hallucinations. The kettle sounded like an untuned radio. The waves against the hull were indistinct voices at a party. Everything was something it wasn’t meant to be.
At 05:00 I pulled myself together, filled myself with more caffeine, shook out the reef and signalled to the engine room for full speed ahead. Finally, at 13:27 we reached the finish line off St. Anns Head and with the little dexterity left in me picked up a Dale mooring buoy after the 3rd attempt. I then flopped down knowing full well I should tidy up first but having only about 2 hours sleep since Looe the bunk was tempting me ever closer.
Chuck then called up to say it was beer o’clock shortly so get yourself together. I didn’t tidy up and sensibly had just an hours sleep, well I couldn’t miss the pub, that would just be rude.
From Plymouth there were 4 finishers (times not important)
| Chuck Dandridge | J’HANA | Sadler | 29′ |
| Gary O’Grady | KATY | Westerly Konsort | 29′ |
| John Moody | BLACK MAGIC | Mirage | 29′ |
| Tony Head | TRIPLE VENTURE | Twister | 28′ |
From Pwllheli 4 boats also made it round
| David Knowler | HEADWAY III | Achilles 840 | 27’8 |
| Geoff Turner | DAWN | Parker 21 | 21′ |
| Mike Lynch | BONEGI | Twister | 28′ |
| Roger Fitzgerald | ELLA TROUT | Dehler | 29′ |
If you are interested in long distance solo sailing get on to the Jester website – https://jesterchallenge.wordpress.com/ It really is great fun.
This article was originally published in the Westerly Owners Magazine.
Jester Challenge 