
Jester's pennant
I had been thinking for some while in taking part in the Jester Challenge. If you don’t know this a single handed event for skippers of small boats under 30 feet who want to test their skill and self-reliance, a uniquely successful experiment in singlehanded ocean sailing.
https://jesterchallenge.org/
I had wanted to take part the previous year as the objective was the Azores but circumstances prevented me. This year’s objective was Baltimore in Ireland. I was in two minds about it but my best friend encourage me so I thought I would give it a go. It would be good to re-visit Ireland because I had not been back since my circumnavigation of Ireland in 2004. From Sea Bear’s base to the start in Plymouth was between 260 – 300 miles depending on the route so that would be some challenge in it’s own right.
1st June Pin Mill to Small Downs 65 miles 17 hours
Left the mooring at 6.45 taking the ebb down the Orwell. Clear of the docks hoisted the main and headed down the Medusa channel and then Goldmer Gat for the Kings Channel which we tacked down. The wind had freshened so the yankee was furled and a 2nd reef put in the main. We took the Little Sunk crossing of the sands and across the Black Deep to enter Foulgers Gat. The wind headed us before the exit so I thought to motor the last bit. Only trouble was no cooling water exiting the exhaust. Thinking it might be a blockage in the inlet I unscrewed the top of the filter only for fumble fingers to drop it into the bilge – whoops. Now the bilge is deep and dark – no chance of fishing it out. As a temporary measure a wooden bung was used and I kept the engine cover off to keep my eye on it.
All the tacking had slowed us down so by now the tide had turned so it was slow progress and it was gone midnight when I anchored at the Small Downs. Getting into the anchorage in the dark was made less stressful as I had a track in the plotter from a previous visit.
2nd -3rd June Small Downs to Newhaven 86 miles 25 hours
No need for a very early start, weighed anchor and made sail with a gentle NW wind.
Some time later was passing Dover and the wind was increasing so a reef put in the main and some yankee furled. By late afternoon we were past Dungeness. A long slow night passage followed, many long tacks and a bumpy sea making it impossible to cook. By dawn we passed the red buoy Royal Sovreign and then later past Beachy Head. I had to wait to enter Newhaven for a ferry to exit. The visitors pontoon was full but a marina staff directed me to a vacant finger berth. I was shattered and after making secure retired to my bunk.
Newhaven
The weather was unsettled for a few days with SW 4-6. It gave me the opportunity to recover. I also managed to locate and fish out the screw top of the water inlet from the bilges. Determined to not lose it in the bilges again I drilled a hole through one of the tops “ears”, fixed a loop through this with seizing wire and then could keep it on a leash.

Hope Inn Newhaven
8th June Newhaven to Osborne Bay 61 miles 17 hours
An improving forecast allowed me to get away from Newhaven. The weather still was not ideal, visibility a little murky so my plan was to take the outer route around Outer Owens. Entering the Solent I crossed the deep water channel and then followed the island shore to enter and anchor at Osbourne Bay. My first visit here and slightly fooled by the flatness of the bays bed, and in the dark my first attempt left me too far out, too near the channel. But easily rectified by creeping closer in.
9th June Osborne Bay to Studland Bay 24 miles 6 hrs
Weighed anchor and off to Yarmouth. I needed to refuel and I must say I found the fuel berth at Yarmouth very easy to use. Then off to Hurst Castle and take the North Channel out of the Solent. Into Studland bay, my first visit here. For some reason I struggled to pick up a mooring buoy, it is not as if I don’t get enough practice with my own mooring.
10th June Studland to Portland 23 miles 7hrs 30 mins
Had a SW of 20 to 25 knots so 2 reefs in main and a partly furled Yankee. First tack well to the south of St Albans Head to clear the overfalls. By the afternoon was wind was easing so gradually shook out the reefs and then a couple of miles of the entrance to Portland harbour with ever decreasing wind and being headed I started the engine, entered Portland harbour and anchored. I was hailed by another fellow entrant who recognised my boat name from the entrants list. We had a bit of a gam about strategy for rounding the Bill. He had tried that morning but turned back. He was going to leave that night to try again
11th Portland to Plymouth 76 miles 19 hours
A reasonable forecast at last, variable 3 becoming E 4-6 later.
I had planed to head out for the East Shambles before heading for the bill. However condition were very benign and suddenly there were hoards of boats heading out and I went for W Shambles instead. It was indeed very calm and just spoilt by a nasty fog bank which reduced visibility for a nervous time.
Fortunately it soon cleared and the Bill rounded in near perfect conditions. There were 20 other sails in sight.
I decided to make use of the forecast Easterlies and make it a long haul to Plymouth direct rather than call in at Brixham, anyway the anchorage there would not be good in an Easterly. The wind was very variable for the passage so I at times I resorted to the engine. My course took me way off shore so it was not until late eve that I had sight of a hazy coastline.
Shortly before passing Start Point light I had the company of a dolphin pod, always a delight.
Much later the wind did indeed blow strong and rain arrived too. After the Mewstone I handed the sails and ran up the eastern channel to finally anchor in Jennycliff Bay with some relief at about 4 in the morning.
12th June Plymouth
The rain continued through the morning but around 1.30 it had stopped and the wind eased so I upped anchor and went into Mayflower marina, the meeting up point for the Jesters.

Refreshment in Plymouth
13th – 14th June
Reprovisioned the boat, did some washing, organised charts for the next leg and attended the skippers briefing and dinner.
15th June Start of Jesters Plymouth to Newlyn
I left the marina around 11 to be ready for the Jesters Start off the breakwater at 12. Good to see so many- 25 small boats setting off together.
It was blowing about 18 knots from SW so I had 1 reef in the main, it felt about right. With this wind direction I knew it would be hard tacking to make progress westwards.
Later that afternoon the Eddystone light and Hands Deep cardinal were off to port. Later that evening the winds fell light and by nightfall and time to switch on the navigation lights there was barely any wind. I could just see the loom of the Lizard light way off the starboard bow.
The night was worrying, no wind, no steerage way, the sails slatting about. I was almost far enough out to be in the shipping lane off the Lizard. I could see the lights of several ships not very far off but there was little I could do about it. Jester rules, such as they are, preclude use of engine except in an emergency, so a sleepless and worrying night.
Dawn came with little change, not even past the Lizard yet and the plotter showed I had been going backwards with the tide. The forecast was not optimistic. A big blocking high was sat over the Scilly Isles so very little likelihood of much wind.
Around 1pm with no progress for 12 or more hours and little prospect of wind I decided to abandon.
I was not alone, after the event I discovered that of the 25 starters from Plymouth 12 had also given up and some of the finishers had used their engines at some point.

track off lizard