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Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility.


The Jester Challenge was created for skippers of small boats who want to test their skill and self-reliance, is a uniquely successful experiment in single-handed ocean sailing. This site tells you everything you need to know about it: its history, philosophy, guidelines and future events, along with the views and experiences of skippers who have taken part over the years.

There is a Challenge every single year and new skippers are always welcome. If you like the idea of developing your offshore seamanship in a relaxed and supportive environment, visit the Jester Challenge website. 

This is the fifth of a 10-part post where solo sailor Bernie Branfield shares his first hand account of his single-handed, 2022 Jester Challenge, from Plymouth, UK to the Azores, in his 26′ Invicta Mk2, Louisa. You can read more about Bernie at the end of the post.


Louisa is about 50 years old, she was very well made as far as I can tell and has been well set for offshore sailing by a pervious owner who kept her in the Mediterranean and sailed her on his own. The last owners didn’t appear to do much with her but kept her clean. Most things seemed to be solid but I hadn’t tested her in all of the conditions I was expecting so I was prepared to sail her cautiously. By this I mean with sheets and halyards cracked off a fraction and plenty of windward traveller. By this approach I would loose 5 to 10 degrees of windward performance which would make me slow but there should be shock absorbency inherent in the running rigging. The standing rigging was relatively new with the lowers having been uprated and replaced last year. The mast had been fully inspected by me and no problems found.

To reach a destination, both the boat and crew need to make it there. This philosophy shaped my sailing and approach to on-going boat management. As an example, I checked the bilges regularly for any water ingress. There was some and I thoroughly check the source which turned out to be one of my water holders that had sprung a leak.

On my way to the start the boom attachment for the kicker cam adrift. The boom had corroded through where the plate was riveted on. I re-riveted it on and determined to not load the kicker up fully when off the wind. A cleat on the mast was removed after the mainsail caught it when being raised. I was continually watching for this type of situation and to help reduce chafing I put PVC sleeving over points of contact such as where sheets crossed guard wires.

I had a set of checklists for daily checks and weekly checks which I managed to keep to as weather would allow. As soon as conditions were suitable I would go forward and check all deck fittings and what I could see from the deck. Nothing required attention except the lower shrouds. At around 10 days in I was reefing and leant back against the after lower starboard stay. It seemed very loose, almost as though it wouldn’t support my weight, let alone the mast! I lowered the main sail and reduced the genoa to less than three reefs in size. In the morning, after worrying all night, I inspected the lower stays and it seemed that the aft lowers had lost a significant amount of tension. It was at this time I remembered that the cheap swageless fittings that I had used and planned to replace prior to departure were still in place. I tried to think of all of the reasons that the stays might go slack and all of the ways in which I could monitor the problem and how I could prevent it from getting worse.

After checking the rigging spares I found all of the parts I was going to use to replace the cheap fittings with: sta-lok swageless eyes, thread lock, extension shackles. It was all there, I just needed flat water to fit them. I even had the Loos tension gauge that a friend had lent me. My strategy for dealing with the problem included setting the main and genoa sheets so that I could reach them from the cabin to let the sails fly if anything changed on the mast or rigging. Reefing deeper and earlier than normal. Running with even more slack in the running rigging to increase shock absorbency. Marking the aft stays, as these seemed to be the worst affected, to check for movement. In hind sight this was near on pointless but worry made me try everything possible to at least monitor the situation. I found some cable grips onboard and attached these so that they were just in contact with the top of the swageless fittings. I then lashed the cable grips to the deck eyes.

Two weeks was a long time to be worried to the point of feeling sick and by the time I was safely in Angra da Heroismo marina and I could check things out I found that the starboard aft lower had slipped a further 1.5mm. The mast had a pronounced rake which it didn’t have when I started.

Also, the grip had twisted in the direction of the thread which seemed to indicate that the wire was slipping out of the fitting.

I replace both of the fittings on the aft lowers which was about 2 hours work. So far the tension has remained constant after around 24 hours sailing between Angra and Velas and Velas to Praia.

Food management onboard was effected by moving a few days supplies of evening meals from the bunk stowage to upper port side locker whenever it was calm enough. For the first week I lived off high calorie snacks as it was too rough to even boil the kettle. Eventually I was able to have a cup of tea and heat some soup up but the cooking arrangements were not going as planned. This got better as time went on and I even managed a corned beef hash which lasted three days and was quite tasty. I knew food wouldn’t be a highlight but at times it was miserable. Towards the end I was able to follow my diet plan but I think I had lost quite a bit of weight. Hydration was a problem early on. I felt sick for the first three days and was having to force myself to drink 2 litres of water a day which wasn’t ideal. I took rehydration salts and vitamin supplements most days which helped.

Clothing became an issue, my carefully packed clothing suffered when one of the vacuum bags leaked so that the contents swelled up and I had to dismantle the bag to get anything out of the locker. By the time I had done this much of my clothing was either damp or in the wrong bag. I made do with very limited changes of clothes until I got to Angra.

Boat cleanliness was an issue as the black mould which I thought I had treated came back with a vengeance. Clothing, sleeping bag, curtains, towel, water proofs were all affected by it and this was quite demotivating. Once in Angra I dried and cleaned every space with bleach solution and used the warmer weather to help dry the boat out. I wish that I had put more effort into this prior to setting off.

Personal hygiene wasn’t great but once I got into my rhythm this improved and the wet wipes and spray bottle worked well. Heads arrangement was standard singlehanded. I was rigorous about brushing my teeth, I mention this because when I was surrounded by dolphins I spat out the spent tooth paste and the dolphins disappeared immediately. This might also work on Orcas and seems a lot less invasive than diesel or bleach that I have seen suggested as deterrents.

Other problems with the boat were limited to losing the damping oil out of the compass when I fell on it and a couple of very minor breakages; a mug and a couple of splinters of wood from the bench slats. Compared to the others I faired very well and it wouldn’t take much to have Louisa ready for moving on.

About Bernie Branfield

I have been sailing since I was 7, I started in Mirror dinghies at the local gravel pit and made my way up to VLCCs for a large oil company as Third Mate. After a break for family life I bought a MacWester Rowan 22’, Chantilly, which I sailed to Holland, Belgium, France and Ireland as well as around the UK East Coast. I still have Chantilly. For a short time I owned an Achilles 24, Mischief, that I had hoped to sail to the Azores but abandoned this plan after an eventful trip back from Ireland. My current boat is an Invicta 26’ Mk2, Louisa, which I bought just before the Covid lockdown. Due to timing, work commitments and various other factors I decided to enter the 2022 Jester Challenge to Newport Rhode Island. When I am not sailing my own boat I try and crew on a yacht delivery each year to build up experience. I have around 30,000 sea miles in yachts and various qualifications including YM Offshore under my belt. Louisa was built in the early 1970s and suits my singlehanded sailing needs to a tee, she is moored at Hoo Ness Yacht Club on the River Medway in Kent.

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