Select Page

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 seventh 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.

Why do I want to try and sail across the Atlantic? I don’t remember a time when I haven’t wanted to, other challenges such as ‘round the world’ or ‘north west passage’ don’t appeal as much as tackling the North Atlantic and never have. I cannot explain it, but since finding out that it was possible in a modest production boat I have had it in my sights. I was surprised to find out that the number of people who have successfully completed a single-handed passage of the North Atlantic, crossing from the UK to NE USA, passing North of the Azores, is estimated to be less than 1,000 people, a fraction of the number who have climbed Everest. This year there have been around 10 single-handed crossings and this was a busy year for events! There is a reason for this, the route is against the prevailing weather and current. Also, the weather is notoriously volatile with frequent storms and the additional hazards of ice and fog in the North Eastern phase of the crossing.

The Jester Challenge presents an ideal context within which to attempt this passage and my preparations over the past five years were focussed towards the full Jester Challenge to Newport in Rhode Island. I believed I had the right boat and the best opportunity considering my age, health and life situation. I became committed to this year’s event when I got my USA B1/B2 visa which had taken almost 10 months.

I derive a great deal of fulfilment from planning and preparing for sailing trips in my various old, scruffy and cheap boats. Seamanship and prudence coupled with the satisfaction of doing more with less motivates me, as does the post adventure glow of making it home safely. Sailing, meeting people and encountering nature are significant factors in choosing adventures. A specific destination is a secondary consideration to the adventure, I would have been just as happy to aim for Boston or New York.

Photo credit: Graeme Shimwell

Getting to the start line was relatively easy as I had started preparations in plenty of time but I was aware that I hadn’t completed a 500nm offshore passage as suggested by the guidelines. Such a passage is not easy to achieve on the East Coast as it is a least two days to a suitable setting off point and then the passage is across the North Sea which is very different to the North Atlantic.

At the start point in Plymouth I was extremely nervous and I am convinced that this stress manifested itself as mild seasickness for the first few days. The first day was a great start but day 2 was a shock to the system. My motivation took a big hit as I encountered the sea state left by the depression that had been stationary off the West Irish coast for a few days. To counter this I retreated and sailed south before I tried going west again. I found it difficult to get into a sailing rhythm and establish a routine. The schedule of taking sun sights and downloading weatherfax transmissions helped with this but I spent much of the time in my bunk reading. In the heaviest weather I hove to, in reality the maximum wind speed was probably force 9 but the sea state was significant, regularly encountering swell and waves totalling 9m with a shortish period between peaks that caused the boat to slam and bounce alarmingly. Although I had the boat under control and safe and I was able to rest, being hove to resulted in no progress or being driven backwards so was a negative factor in my state of mind.

My morale hit a low when I encountered the second weather system. This was after being becalmed in the bay of Biscay and making very little westerly progress. A combination of lack of progress, the tough conditions and discovering a problem with the boat exacerbated the situation. Whilst I was setting a reef in the main sail during the night I found that a lower stay had lost tension. Thoughts that went through my mind were mostly rational but the overriding thought was that I could lose the mast. With the sails stowed I waited for daylight to assess the situation. All four lower stays seemed slack but only one seemed very slack. This was difficult to assess as the boat was bouncing around a fair bit. I determined to try sailing but under reduced canvas. With a small jib set (about 5 turns unfurled) I managed to make some progress but I needed to work out how to manage the situation. Tightening stays in open water, especially when sailing, is very dangerous as any slack that is taken in can either lead to over tensioning the rig or accelerate the onset of the problem. As it turned out it was a good thing that I didn’t apply any addition tension as a swageless fitting was slipping and adding tension would increase the chances of the fitting failing. It was at this time that I received a message that for some reason settled my nerves, gave me hope of a positive outcome and reminded me that I was not alone. The message had nothing to do with the rigging as I had decided to not worry anyone with this news until I had a better handle on it. My motivation improved as I found that I could set sail with an extra reef in without putting undue stress on the rig. Where normally I would sail with 2 reefs I was now sailing with 3 reefs. This had two effects; my westwards progress was hampered as I could only get within 70 degrees of the wind but the boat didn’t slam into the sea so much. Things became more comfortable but progress towards Newport became almost negligible. It was at this point that I decided to head for safety so that I could assess the rigging problem and consider my options. Closest land was A Coruna in Spain, the Azores was still over 600nm away. I determined to give it a day of trying to make progress towards the Azores and then review my plan. Practical steps that I took to deal with the rigging issue included fitting cable grips to the stays just above the swageless fittings, adding lashings to the secure the cable grip to the deck fitting, taking the main and jib sheets into the cabin so that I could release them quickly if I detected a change. This all occurred around day 10. The worry created by the rigging situation and lack of progress seemed to make me feel seasick again.

By day 14 I was 600 nm from the Azores and progress in that direction, although very slow, seemed possible.

I resigned myself to slow progress but when I became becalmed yet again on day 17, my state of mind took a severe dip as the boat appeared to be shaking itself to bits in the slack swell. Ignoring the Jester rules I used the engine to stabilise things and get out of the centre of the high pressure I had ended up in. On day 19 I had the best day of the whole passage. I was surrounded by dolphins in the morning for about an hour, long enough to video them from the bow. Again in the evening I had dolphins, probably the same pod, and they came back after the sun went down. In the dark the light show that their activity generated in the phosphorescence was incredible.

Food was not a consideration in terms of motivation when I was planning the trip. This was a mistake, I took some treats, mainly sweets and hot chocolate drink but they were relatively ineffective in terms of improving morale. Fresh fruit played a part and when the oranges ran out on day 15 I missed this part of my diet. I got bored with much of the food and don’t want to have to eat TVP for a while but sardines are amazing and I didn’t tire of eating them. Knowing what I know now, fresh veg and the ability to cook with them will form part of my future adventures. Corned beef hash was great but the quantities from a standard tin of corned beef made it a bit overwhelming; three meals of corned beef on consecutive days was challenging. Plain water, especially water treated with aquatabs, was hard to consume, the addition of orange flavoured vitamin tablets helped. At the start I struggled to ingest 2 litres of water a day in drinks and cooking. Rehydration tablets were vital and provided a good pick-me-up. The best short term motivational consumable was a nice cup of tea after completing a task such as reefing, navigation, messages etc.

As I approached Terceira I was determined to make a landfall at Praia do Vitoria so stayed up all night hand steering. By day break the wind had got up and the low that was to my North West started heading me so I was gradually pushed south of my intended route. I kept going as the sea state built up until I was south of Terceira and then I headed for Angra do Heroismo, engine on and making 1.5 knots into the wind and waves. This was ideal for arrival at first light. The auto-helm couldn’t maintain a course in the sea state so it was another night of hand steering. When I dropped anchor in the bay at Angra it was with tremendous relief but relatively little sense of achievement. Slowest passage to the Azores that I am aware of, intended destination some 2,500 nm away or 7 weeks at current rate of progress and a problem with the boat. The problem with the boat’s rigging was doubly de-motivating because I had identified the issue before I set off, bought the parts to deal with it but for some reason hadn’t got round to it. Once I had overcome my frustration and embarrassment of this situation it turned into a positive as I had all of the parts onboard to rectify the situation including a Loos gauge to check tension. Morale and state of mind rocketed when I made it onto the marina, people were so helpful and the achievement of an offshore passage had started to sink in but I was exhausted.

If this had been a coastal cruise there were times when I would have dropped the anchor and waited for things to improve, that isn’t an option offshore. I just had to keep on going and this in itself is a mixed blessing as far as motivation is concerned. I was forced to keep going, even if it was to a destination I hadn’t chosen and the thought of turning back or heading to Spain was demoralizing. As it became clear that I wouldn’t make it to the USA but the Azores looked to be a real possibility my motivation improved. There was a day when nothing went to plan, during the day I was both hove to and pushed backwards. I fell over getting back into the cockpit and damaged the main steering compass. To break the sequence I hove to, got into my bunk and slept.

I was expecting the encouragement and concerns of people ashore to have an influence on my motivation. This turned out to be limited and apart from restricting the detail of my situation in my messages there were only a couple of occasions when communications had a significant impact on my morale. Forecast wind speeds were, at times, significant under estimates of what I was experiencing and this was disheartening. At no point did I consider the progress of other challengers or what people would think of where I might end up. Later, I discussed my passage with a very experienced couple who I met in the Azores and they didn’t think I was a natural single handed sailor. Initially this was a bit of a knock but when I analysed it they were correct. More than about three weeks away from people and society exceeded my threshold for isolation.

I was expecting some highs and lows on the trip but not the depth of the low of being ground down by the sea state and the rigging problem. Upon reviewing my log I had one day when everything seemed to be against me and this was a day when I had hoped to make progress but the sea state was such that progress wasn’t possible. I reckon I had three good days out of 25. Day 1 was a great start, day 19 with the dolphins and reasonable progress was the best day. Day 11 was also good as that is when I first considered going to the Azores and I overcame my initial fear that the mast was about to fall down.

Am I motivated to have another go? It is too early to say if I would attempt the full North Atlantic challenge again but I would definitely set off for the Azores at the next opportunity.

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.

Wooden Hulls – Part 1

Traditional wooden boats have a plank on frame construction, a centuries old boat building method that is still in use today. Variations of the traditional method include carvel, clinker and strip planking, which all relate to the way the planking is attached to the frame.

Boat surveys

A full boat survey assesses the condition of the hull, mechanical gear and means of propulsion. The survey is carried out with the boat...

Common medical emergencies at sea

A medical emergency aboard a boat at sea requires immediate attention to ensure the safety of the casualty and the crew in general. The skipper needs to know which crew members, if any, have had medical training or have a first aid qualification. All boats should carry first aid handbooks to help an untrained crew cope with a medical emergency.

Sail trimming for cruisers

Sail trimming tips for cruisers. Whether racing or cruising, a well tuned boat will sail faster and tend to heel less than a boat with badly adjusted sails.

ColRegs when sailing single handed

  Don’t neglect the Colregs when sailing single handed Sailing single-handed represents several challenges for skippers, not least how to...

Understanding tide tables and tidal curves

There are many factors that influence local tidal patterns and it’s essential for every sailor to have a good understanding of tide tables and tidal charts to ensure they can calculate the level of tide at any given time.

Essential Knots: Round turn and two half hitches

Essential Knots: Round turn and two half hitches Use: Tying a rope to a pole or a ring. Step 1. Pass the end around the object. Step 2....

Avoiding collisions at sea – how to stay safe on the water

Boats have many blind spots, including the headsails of sailing boats. Always keep a lookout, stay safe and remember that...

Top Ten Tips For Learning The ColRegs Boating Rules Of The Road

Colregs Boating Rules Of The Road Skippers struggle to learn and remember the ColRegs Yachtmaster and Day Skipper course...

Seized fixings and fastenings

Maintaining a boat can be a rewarding experience but at times it can also be frustrating. A prime example of this is when you come across a seized fixing or fastening that refuses to budge. Read our tips on how to release and fix them:

Hourly Checks when sailing or motoring

  Hourly Checks Get into the habit of carrying out these checks and both yourself, your crew and your boat will be...

Diesel engine winterisation

An inactive boat engine needs to be protected from corrosion during the winter, caused by the rising humidity levels through the cold months and the salty coastal air. This applies whether the boat is left afloat or hauled out over the winter. Read here about the two important stages of winterisaton for a diesel boat engine.

ColRegs Nav Lights & Shapes, Rules Of The Road and IALA Buoys Apps

ColRegs Nav Lights & Shapes, Rules Of The Road and IALA Buoys Apps Make Learning Rules on iPhone, iPad, iPod and Android...

Passage Planning Advice & Safety for skippers

Passage planning helps you to: • Decide where to go • Calculate how long it will take to get there • Avoid bad weather •...

Getting a tow for your sail or power boat at sea or on inland waterways

FREE tips from the Safe Skipper App for iPhone/iPad/Android: Getting a tow for your sail or power boat Plan how to secure a...

Gybing a sailing boat

Gybing is the sailing manoeuvre used to change a boat's direction through a following wind. As with the tacking manoeuvre,...

Wooden Hulls – Part 2

It is important to ensure the essential hull maintenance of a wooden boat is done, even if you are paying others to look after your boat for you. The priority is to prevent rot from taking hold. The protective layers of paint and varnish over wood are far more critical than on GRP boats, where the topsides are painted more for cosmetic reasons.

Antifouling for leisure boats – Part 1

Boats that are kept afloat can very quickly become a home for small marine organisms such as barnacles, weed and slime. Applying an antifouling paint to your hull is necessary to protect it from these micro-organisms, as a fouled hull can cause problems and will slow down a boat’s maximum speed considerably if left unchecked.

Boat maintenance below decks

While most interior maintenance work can be done when a boat is afloat, some jobs such as servicing the seacocks have to be done ashore. It makes sense to do any major interior repairs and improvements with the boat hauled out in the boatyard.

Steel hull maintenance

A steel boat owner’s biggest enemy is corrosion. You don’t have to worry about osmosis or rotting timbers, instead rust is the number one issue that will keep you awake at night.

Fixing position at sea using traditional methods

This post looks at some traditional methods used for fixing a vessel’s position at sea, within sight of land. Electronic fixes using chart plotters are very straightforward to record, but if for some reason a vessel’s electronics are faulty it is essential that a skipper knows how to use traditional methods.

Passage planning and pilotage

Passage planning and pilotage help skippers navigate safely from one port to another. A passage plan takes into account all...

A five day sailing cruise of the Solent, UK

Welcome to our virtual Solent sailing cruise – a five day sail in the south of England from Bosham Quay in Chichester...

Learning about diesel engine maintenance

Marine diesel engines are internal combustion engines that are designed specifically for use in maritime applications. These engines are commonly used in a variety of watercraft, ranging from small boats and yachts to large ships and vessels. Learn about marine diesel engine maintenance courses.

Boatyard Health and Safety

Boat storage facilities are potentially hazardous environments and it is the responsibility of both boat owners and boatyards to ensure that the...