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 fourth 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.


The passage plan I had identified is termed the southern route. In theory this avoids the heavy weather on the shorter great circle route where the Atlantic depressions run against the direction of travel. The great circle route also has the strong possibility of ice and fog banks off Newfoundland. I don’t like fog, I am terrified of ice and I prefer slightly warmer, not hot, weather. There is a mid route but unless the boat you are on is low displacement such as a multihull, the gulf stream can account for up to 30% of boat speed for the final third of the passage. The southern route is about 700nm longer than the great circle route and the plan was to sail south west to 40N and then west south west below the gulf stream until south of Newport then head north to cut across the gulf stream at its narrowest point. So with this in mind I set off in a south westerly direction, problem was that the weather was moving from the south west towards the UK and a day out of Plymouth I reached the edge of a depression that had been sat off the UK for the previous 48 hours. The sea state had built up and heading south west was not an option. Between heading north west or south I opted for south. This took me into the bay of Biscay which I had been hoping to avoid but it turned out to be calm, I was becalmed for two days in the bay. To get back on track I tried heading west again but further weather systems pushed me south.

Navigating to way points on an ocean scale was new to me and I tried to keep in mind that 100nm off track is irrelevant if that is where the weather puts you. I use my Matsutec AIS navigator to monitor progress towards way points and on this passage it kept me on track through a combination of range reduction and course to steer changes. I opted for the heading that I could achieve that caused the range to reduce and if this put me into heavier weather then I opted for increasing bearing. Increasing bearing has limitations as it is very slow to respond over the ranges in question. By setting sub waypoints at shorter ranges this became more usable. After the third weather I was able to make progress in the desired direction, albeit I would have preferred to have been level with the Azores by now.

As luck would have it a friend had lent me his spare Azores pilot book so I had no qualms about navigating to the Azores, I had downloaded Navionics for the Azores as well. Anyone who knows me will appreciate that the Azores has far more appeal to me than almost anywhere else. So I changed plans and headed for the Azores. The passage making became easier as did almost everything with the exception of my worries about the rigging. There was a final sting in the tail, the fourth weather system of the trip caused me to divert to Angra do Heroismo instead of Praia do Vitoria which had been my preferred port. This was the final nail in the coffin of thoughts of Newport. When I was in the lee of Terceira I turned the engine on and motored the final 10 miles into the anchorage at Angra and promptly retired from the challenge.

In parallel with the GPS navigation offered by my AIS / Navigator unit and the other half dozen GPS devices I had on board I ran celestial navigation. This comprised a morning sun sight followed by a noon sight. The reasoning for morning sights was that if I missed one I had the contingency of an afternoon sight. In practice afternoon sights are probably better as they give a position line that is perpendicular to the direction of travel and therefore a better indication of progress. Noon sights were taken whenever the sun was available and it wasn’t too rough. I clocked up 13 noon sights in 24 days, I also managed 21 sun sights, a moon sight and a dubious Polaris sight in this time. The main reason sights were not achieved was cloud cover, also boat motion accounted for a significant number of missed sights. If I used a GPS derived estimated position then my intercepts were within 5’ of arc, noon was within 3’ of GPS latitude. I had confidence in my sights and the calculations. I didn’t even attempt a star sight, there was too much cloud cover, boat motion made the administration of stars problematic but I did practice locating and shooting individual stars when conditions allowed.

What wasn’t so good was my dead reckoning work. Monitoring course and speed for any duration was almost impracticable in all but the most steady of weather. As the wind speed and direction changed so much, on average I was changing sail plan 6 times in any 24 hours, that it proved impossible to achieve a dead reckoning position that gave anything better than an intercept of 15’. If I had kept better records of travel and plotted then on a sheet this might have improved the accuracy.

I was able to navigate using celestial bodies and my 4 figure Reeds almanac tables. With a land fall on Terceira of 25nm I would have been successful but being on my own and given the weather conditions I wouldn’t have been confident in my position keeping with just celestial navigation. I used a pad of universal plotting sheets and this worked well but had the limitation of the centre fold where a protractor wouldn’t lie flat. I achieved 13 daily plots but of these only 11 gave a usable position which was typically around 10nm out from GPS. My assessment of each plot identified poor DR work as the main cause.

My sextant is one I have had for a very long time, some arm chair navigator told me it was useless on a boat because it had the wrong telescope. It worked for me and when it was very rough I used it without the telescope. My chronometer is a cheap Casio F-91W wrist watch that I rated over an extended period. It lost an additional 2 seconds against rating over 25 days of fairly rough water sailing.

You can read the complete story on Bernie’s blog page here.


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.

Competent crew skills: mooring lines

Mooring lines are used when arriving or leaving a berth. One of the most important competent crew skills is to know how to...

Wooden Hull Repairs

While wooden boat hull maintenance is mostly straightforward, it is always a good idea to take expert advice on any repair job needed doing to a wooden boat, unless you have done the job before and know what you are doing.

Cleaning & polishing painted topsides

The gelcoat topsides of a GRP boat can be pampered and restored to their former glory relatively easily when it is ashore. Gelcoat is only a very thin outer layer of the hull, often less than 1mm thick, so you should avoid cleaning it with highly abrasive cleaners, or an-ything that could potentially damage its surface.

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.

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...

Points of Sailing

The course on which a boat is sailing can be described by its angle to the wind, not to be confused with its compass...

Essential Knots: Sheet bend

Essential Knots: Sheet bend Use: Joining two ropes together. A sheet bend is particularly useful for joining two ropes of different...

Jester Challenge 2022 – Sailing single handed from Plymouth UK to the Azores: Part 6 – Communications

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

Navigation safety: a quick-reference mobile app to learn the ColRegs NavLights and Shapes

 Safety at SeaSafety at sea will always remains a topical and important subject that will no doubt dominate the syllabuses of nautical...

Essential Knots: Clove hitch

Essential Knots: Clove hitch Use: Tying a rope to posts, bollards, rings or a guardrail. Step 1. Make a turn around the object and lay...

Boat engine fuel system

If engines are installed and serviced correctly then most marine engines are very reliable, but one of the most important parts of the engine to check and service is the fuel system.

Jester Challenge 2022 – Sailing single handed from Plymouth UK to the Azores: Part 10 – The Return Trip

Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility. This is the final instalment 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.

Keel maintenance and repair – Part 1

Keels are designed to act as underwater foils that generate lift as the boat moves through the water, counteracting the leeward force of the wind and enabling the boat to sail closer to the wind. Keel maintenance and repair is essential for the performance of your boat.

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.

Top five windvane self steering installation questions

Top five windvane self steering installation questions answered by Sarah Curry of Hydrovane International Marine, courtesy of Viki Moore from Island Cruising NZ

Tips and advice for staying safe on a sailboat at sea

Here we focus on how to stay safe on a sailboat at sea. We cover key things to ensure you have on board before you set sail as well as covering the most common cause of incidents on sailboats and how to deal with them.

Boat ownership – some fundamentals

Owning a boat is a big commitment that should bring no end of satisfaction, but the costs of maintaining and keeping a boat are significant and should never be underestimated.

First aid at sea basics

At least one person on board should be trained in first aid and know how to administer the contents of the first aid kit, ensuring there are adequate supplies for the planned duration of the trip.

Understanding boat engines

Irrespective of what kind of engine a boat is equipped with and who does the work, the regular care and maintenance of a marine engine is essential. The most common cause of marine engine failure is widely known to be lack of maintenance.

Medical Emergency at Sea

How to deal with a medical emergency afloat   If you are planning a boating trip, it is important to have at least one...

Seacock maintenance

If seacocks are always left open and neglected they can eventually seize which will prove a serious threat to boat safety should a connecting hose fail and the seacock refuses to close. There are three main types of seacock – ball valves, cone valves and gate valves.

Sector lights, directional lights, leading lights – how do they differ?

Sector lights, directional lights and leading lights guide vessels safely through hazardous waters or narrow channels at...

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...

Dripless shaft seals

Dripless shaft seals are designed to completely stop water from entering a boat’s hull via the stern tube. There are two main types of dripless seals known as face seals and lip seals which many boat manufacturers now fit to production boats.

Passage planning and pilotage

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