The art of sailing a small boat single-handed for long periods has been perfected by the 2023 Jester Challenge sailors. Jake Kavanagh picks up some tips for keeping skipper and boat safe on extended passages...

You don’t need a large boat to sail offshore, you just need to be well prepared – as Jester Challenge veteran and offshore adventurer, Roger Taylor has proved numerous times. Many leisure sailors will face a situation when they need to make a long passage with inexperienced crew, or perhaps with no crew at all.

While single-handers are often criticised for not being able to keep a proper lookout, a tour of some of the boats collecting for the 2023 Jester Challenge proved just how well-equipped and safe they all were.

As one skipper put it, “I could have a crew of two with me. But what if one – or both – get seasick? Then I not only have the boat to look after but also two incapacitated adults. In that situation, I’m much safer on my own.”

Starting from Plymouth and Pwllheli, this year’s challenge saw boats sail about 250 miles across the Celtic Sea to the Republic of Ireland. As the voyage could take anywhere from 60 hours to six days, the sub-30ft yachts in the fleet were all suitably equipped.

They were also completely mismatched in a way that would bemuse an official race handicapper. This is another reason why the Jester Challenge (JC) concept is not classed as a race, just a group of like-minded individuals challenging the sea.

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As a long-term supporter of the event, PBO managed to get aboard several JBC yachts at the Plymouth start to see how they’d been modified for solo long-distance sailing. Most were popular production models, such as Westerlies, Sadlers, Twisters, Moodys and Colvics, with one or two notable exceptions.

As such, we could see how many of the modifications would work on any yacht that needs to sail single-handed for more than 24 hours at a time, the usual limit of human endurance without sleep. Here are some of our favourites.


Jesters rarely steer their boats except when entering or leaving harbour. On passage, the job is given to some kind of self-steering system, most commonly a transom-hung windvane device.

The budget-priced Hebridean is popular. The metallic parts are bought as a kit, then the wood sourced independently and cut to shape

These hold a steady course in relation to the direction of the wind, working tirelessly day and night without requiring a single amp of electricity.

Instead, the considerable force required to work the yacht’s rudder comes from a thin blade trailing in the water, which is twisted out of alignment by the vane when the yacht wanders off course.

As hydro-dynamic forces push the blade upwards, they are harnessed by lines attached to the tiller (or wheel) to restore the heading. The only downside is that if the wind shifts direction unexpectedly, then so does the yacht.

Usually, a simple adjustment to the windvane using thin lines from the cockpit is all that is needed. Some electro-mechanical pilots were also in evidence, although these are mainly used between challenges when the boat is motoring in light winds.

With the engine alternator providing power and the hull pushing into a relatively calm sea, these wheel or tiller-mounted autopilots do a good job. They also act as a back-up if the windvane fails, but tend to be heavy on amperage, especially in rough weather.

The JBC fleet of 33 yachts in Plymouth (and another 10 starters in Pwllheli) sported many of the most proven designs of windvane on the market. These ranged from the ‘Rolls Royce’ of models, the UK-made Hydrovane, to a relative newcomer, the kit-supplied and budget-priced Hebridean.

The US-made Monitor’s manufacturer has a large archive of installation reports on most yacht designs. The unit is bulky, but robust

More well-known makes included Sea Feather, Navik, Wind Pilot and Monitor, and a couple of examples of DIY ingenuity.

While windvanes are expensive, even second-hand (prices on eBay range from around £650 for a used Navik to £3,500 for a used Hydrovane) they are a huge enabler for a long passage.

Once installed and bedded in, they need very little maintenance, either.

Staying awake

According to the sleep science website Healthline, an adult needs between seven to nine hours of ‘good quality’ sleep each night.

Staying awake non-stop for 24 hours can result in impaired decision making, altered perception and decreased hand-to-eye coordination. The longer you go without sleep, the more pronounced these issues become.

After 36 sleepless hours, you can add decreased motivation and ‘inflexible reasoning’ to the mix, and after 48 hours you’ll start to experience hallucinations, anxiety, and paranoia. Even the simplest tasks will prove almost impossible to complete.

Santa as the little helper. A simple kitchen timer – this one for basting Turkey – allows skippers to use ‘polyphasic’ sleep patterns (power naps) to stay as alert as possible over long passages.

For single-handers, with no able crew to take over, sleep deprivation is a key issue. The answer is to adopt a system of polyphasic sleep, or power-naps. Many of the Jesters use a simple kitchen timer, usually placed out of reach so they must get out of their bunk to turn it off.

Most set it to 10-15 minutes, the time before a relatively fast ship could get on top of them from below the horizon. On the Baltimore Challenge, the skippers decided to stay continuously awake in the shipping routes around Land’s End and then bring in the power naps once further into the Atlantic.

One even proposed anchoring off the Isles of Scilly to catch up on sleep if necessary. The key to successful solo or short-handed sailing is to grab regular short naps to preserve decision making abilities.

Deck lifelines are kept short so they can be used as restraining lines. This one holds Ron Olivier firmly against the deck as he works the base of the mast of his Westerly Griffon

Clipping on

The best way to avoid a man overboard situation is to not fall overboard in the first place. All the 2023 Jester Challenge skippers we spoke to were fastidious about their lifelines, with many fitting additional handholds on deck to increase traction.

Some also had folding ladders that could be pulled down with a trailing line, although opinions were mixed about how effective these ladders can be.

Getting the bottom step deep enough for a good purchase was one discussion, while the tendency for rope ladders to swing right under the hull when being climbed was another. The real issues for single-handers arise when they need to work the mast.

Many have led halyards and control lines back to the cockpit, but there will still be occasions when a walk on deck is required. Even in the calmest of seas, the skippers invariably clip on. If they fall in, the boat can quickly drift away from them with even the slightest puff of wind.

A general theme is to have the jacklines inboard, rather than running along the deck so that the lifeline from the body can be as short as possible. As you can see from the images, the lifeline can then be pulled taut, so it acts as a third leg, but one that is actually pulling the body against the deck. Many Jesters preferred tape jacklines to wire versions, as they don’t roll underfoot.

Nearly all the stoves we saw were gimballed to some extent, with the Origo alcohol models very popular due to their non-explosive fuel. The low-tax industrial alcohol is readily available in bulk but resist the temptation to fortify your gin with it. Something foul is added during manufacture, apparently.

Victualling and cooking

A figure that often comes up in small boat voyaging is ‘10lb (4.5kg) of supplies per day’. This is the minimum weight that should be allowed for all your consumables, from water and food to toothpaste, cooking gas and even loo roll.

On top of that, you must factor in a 20% reserve in case of long periods of becalming or stoppages from equipment failure. For the 250-mile Baltimore Challenge, this is rarely a factor, but for the small boats attempting a month-long Atlantic crossing, provisions and storage start to become a major consideration, especially with trim.

Compact and quick heating camping stoves are ideal for a cup of hot water for hydrating dried food in bad weather

Jesters joke about suspending any weight-loss diets on passage as the constant movement helps to burn the calories instead. Biscuits, buns and other high calorie ‘comfort’ foods were in every victualling basket. In the smallest boats, water was often carried in a series of 10lt containers, as this allowed them to be moved around inside to aid trim.

(I once added a knot to my 21ft Corribee’s cruising speed by filling the bow up with wine from a French hypermarket. Dropping the nose gave a longer waterline, so our passage home was considerably quicker.)

Cooking on passage relied on some standard marine stoves, although we saw a lot of Origo alcohol burners among the fleet. These cookers give a clean and non-explosive flame, and the low-tax alcohol is readily available to buy online. “Don’t try and drink it,” one skipper advised. “They put something pretty horrible in it.”

These alcohol stoves present a much safer alternative to gas, especially where having the room for a dedicated and well-drained gas locker on a small boat may be tricky.

One skipper installed his Campingaz bottle in a locker directly beneath his gimballed stove, as it was easier to turn it off there rather than battling outside to the locker in poor weather.  “I’d be tempted to leave it on in those circumstances, so this arrangement is actually safer,” he explained.

Boat-mounted EPIRBs and body-worn PLBs were in widespread use. Skippers were diligent in ensuring boat and contact details were up to date on the coastguard database

Staying in touch

Family and friends will worry about you. (And you should worry if they don’t.) For single-handers, once out of cell phone range (usually about five miles offshore, although wind farms will soon carry repeaters) and VHF radio (up to 40 miles, but often much less) the skipper is effectively on their own.

For some Challengers, this is part of the appeal. The advent of much cheaper satellite comms, however, means that they can keep the family informed of progress with a simple text message from a battery-powered device via a subscription service.

Many of the skippers had invested in systems such as Spot, Iridium GO! or the Garmin In-Reach system. These allow family and friends to track progress visually via an automatic position report, and for the user to send a simple code for a back-up message.

If the yacht doesn’t appear to move for a day or two, for example, and the family fears a dismasting or health issue, the skipper can send ‘All OK’ or a similar pre-loaded message. Some of the more advanced systems will allow for a few extra lines of text.

These devices and their subscriptions aren’t cheap, although prices are coming down as more satellites go up, but they are invaluable in keeping the family apprised. Should things go wrong, there is an SOS function which, a bit like the big red DSC button on a VHF, sends an automated distress alert with an embedded real time position as a data burst.

Some also provide a function that shows the distress alert has been received; this has also been recently added to some Emergency Position Indicating Radio Beacons (EPIRBs) as well.

Bob Litton has devised a way to quickly remove his vertically mounted Sunpower PV panels in case of heavy seas. He fears a broadside wave could flex them beyond their limits.

Generating power

Jester Challenge yachts generally have low power demands and are allowed to run the engine (in neutral) on passage to top up the batteries, but most skippers prefer to harness renewables. While there were a few wind turbines in the fleet and an occasional hydro-regenerator, the bulk of renewables came from solar panels.

As the boats are quite small, these panels take up valuable deck space, so are usually thin flexible versions that are easy to detach and stow. Many skippers find their panels work quite effectively in the vertical position, harvesting reflected UV off the sea as well as directly from the sun.

Directional panels with a friction lock usually provide the most power. German skipper Erbhard Harms hopefully hunts for the sun from the cockpit of his Allegro 27.

As such, these panels are often incorporated into the spray screens on each side of the cockpit. However, Bob Litton has developed a quick-release system for his thin, dodger-mounted panels as he feels the impact of a broadside wave could exceed the recommended flex limits.

Meanwhile, to conserve power underway, most of the yachts have LED navigation and interior lights, with very few running any high draw items such as large refrigerators, tiller pilots or electric toilets. Simplicity in electrical systems means greater self-reliance.

Electronic watchkeeping

At 30ft/9.1m LOA or less, only a few Challenge yachts were big enough to carry radar, despite the compact size and improved energy efficiency of modern sets. However, nearly all had AIS (Automatic Identification System).

Nearly every yacht had an AIS (Automatic Identification System) VHF set installed. This is the set up on the Tiki 30 Moana showing a wide range of instrumentation. Paper charts are also used for navigation, although they are being phased out by the hydrographic office in favour of electronic versions.

The advent of AIS has made navigation so much safer as it allows similarly equipped vessels to not only identify each other at a distance, but also see how fast they are going and in which direction. AIS also allows for a targeted broadcast to a vessel of interest, so you can call it directly using its unique Maritime Mobile Service Identity (MMSI) number.

This will often be shown next to its icon on the display screen and can be used as a ‘speed dial’ function on some DSC (Digital Selective Calling) VHF sets. Click on the number for automatic dial up, and you can quickly connect to the ship that’s bearing down on you. Many potential collisions have been avoided this way.

We used AIS very effectively at the start, as former Jester Azores Challenge skipper John Willis zipped around the fleet in his Channel Islands 22 motor cruiser for the photography – using AIS helped us pick out the Jesters from the many weekend sailors who were also enjoying a sail in Plymouth Sound and gave us a clear track to intercept them.

Loss of the rudder in a blow could be a game changer, so George Hunter made this nicely crafted emergency version for the outboard well of his Hurley 22

Guard zone

Most AIS sets are equipped with a guard zone function, so a Jester skipper can be audibly alerted if the set is pinged by another AIS-equipped boat at a pre-set range. (Vesper Marine even has a human voice to describe the problem, such as “Target approaching fast on bearing 180°.”

As an additional safety feature, they have programmed the voice to get more annoyed the longer it is ignored). This guard zone acts as a very effective lookout and early warning system when on passage. However, a note of caution – not all vessels are required to carry AIS, especially leisure craft of less than 20 metres.

Of the vessels for whom AIS is mandatory, some fishermen even turn off their sets when in their secret fishing patch, so the system remains far from infallible. For the Jesters, though, it is a lifesaver, especially when combined with other good watchkeeping practices.

The sets are not particularly expensive, so make a sound investment for all types of offshore cruising. The Jester Baltimore Challenge is seen as a warm-up challenge to the big ones, so many first-time Jesters take the opportunity to equip their yachts in anticipation of an off-soundings sortie.

Apart from using advanced weather forecasting solutions (Weatherfax or satellite services such as those provided by Garmin’s In Reach handsets), Jester skippers have also prepared their boats for when they simply can’t out-manoeuvre an approaching storm.

The series drogue is a popular addition to storm survival kit. This one was made as a lockdown project by Ron Olivier for his 26ft Westerly Griffon. Photo: Ron Oliver

One very effective way to keep a small boat under control in heavy seas is to deploy a drogue. This acts as a kind of ‘handbrake’ and keeps the stern (or bow if preferred) into the weather, preventing the hull from turning sideways across a wave and broaching or, worse still, running too fast down a wave and burying her nose.

This can result in a stern-over-bow somersault known as a pitch-pole. Many have taken advice from the books of solo sailor Roger Taylor, one of the trio of ‘Jester Helm’ organisers, who had driven for 16 hours from the Scottish Highlands to attend the start.

In his forays into the Arctic Circle in his engineless Corribee 21, Mingming, Roger had successfully deployed his Jordon Series drogue during a deep Polar depression. The drogue consists of a series of small cones sewn firmly into a long piece of sinking line which is attached to reinforced plates in the hull.

The cones are too small to be ripped apart by fast-moving water but big enough to collectively slow the boat so the weather rushes harmlessly past. These drogues are not the easiest things to recover afterward, requiring a considerable amount of strength, time and patience, but when deployed make a huge difference to the survivability of a small boat in mountainous seas.

Other precautions we saw were devices for emergency steering, easily deployed liferafts, and handy grab bags. Several skippers had also invested in laser flares to supplement their time-sensitive pyrotechnics.

Bob Litton has created a step at the rear of the cockpit so he can look over the sprayhood, and also a stainless steel cage for hand grips when he works his way forward

Better cockpits

With skippers intending to spend a lot of time in the cockpit, an area that often represents about a third of the living space available, some ingenuity goes into making it as comfortable as possible. Several skippers had added occasional seats to various parts of the cockpit, where they could wedge themselves underway.

Others have tackled the issue of lack of headroom by modifying the main hatch with either a Perspex blister or a custom-made doghouse. Washboards have also been modified to be leakproof. A wave taken ‘green’ over the stern can ‘squirt’ around the end of standard washboards, which lack the compressible rubber seams found in car doors.

These jets of water can often spray over the electronics at the nav station, so one boat had added a permanent spray shield beside the companionway steps. Another answer is to have doubled-up washboards, or to place a canvas dodger on the outside.

Graeme Shimwell has created this fabric spray excluder for his Albin Vega 27. This prevents washboards leaking around the edges if hit by a wave or angled heavy rain.

Visibility forward is also a consideration, and one boat also featured a small platform at the rear so the skipper could see over his sprayhood. Meanwhile, Good Report featured a sprayhood extension which gave much more protection further back from the companionway.


Looking at the preparations on board, it was easy to see that these small boats were ready for pretty much anything. Under the mantra ‘Seamanship without showmanship’ each Jester yacht was an example of self-reliance, partly helped by over-engineered equipment and providing for worse case scenarios.

If you have a long trip planned and are a little anxious about whether you or the boat are up to it, hopefully the modifications, ideas and mindset of this modest band of enthusiasts will give you the confidence to crack on with your plans. If you’re feeling particularly encouraged, then the next Jester Atlantic Challenge is in 2025.

Hopefully, the small sample of the dozens of ideas we saw this year will fuel your creativity.

About the Jester Challenge

The Jester Challenge is an annual event with a few simple rules. First and foremost, it is not a race, just the pitting of a relatively small boat against the sea. For entry (which is free) the boat must be less than 30ft (9.1m) LOA and skippered by a single-hander over the age of 18.

The voyage must be completed under sail only, except in an emergency. The only other proviso is the signing of a waiver to say you’re fully responsible for your own preparation, choice of equipment and safety.

The starting port is Plymouth or Pwllheli. The destinations increase in distance in a revolving cycle over consecutive years, namely Baltimore in Southern Ireland (250 miles), the Azores in mid-Atlantic (1,400 miles) and Rhode Island in the USA (3,500 miles).

Apart from the usual berthing charges in the host marina (often discounted) there are no other fees, no prizes or sponsorship, and no scrutinising. You’ll find much more information at

Talented Duncan Lougee sailed his 25ft folkboat hundreds of miles without a rudder in 2021, but was tragically lost at sea ‘on a relatively short passage in benign weather’ in June 2023. Photo: Roger Taylor

The sad loss of Jester veteran, Duncan Lougee

As a result of skipper’s self-reliance, the Jester Challenge has had an impeccable safety record. Unfortunately, during the 2023 Jester Challenge in June, the event suffered its first-ever loss, and to one of its most experienced yachtsmen.

Veteran Challenger Duncan Lougee was first reported as overdue and uncontactable, and then missing. After a wide search by both UK and Irish coastguards, his 25ft (7.6m) Folkboat Minke was found adrift in the Celtic Sea.

Duncan is presumed to have been lost overboard, and with the yacht now recovered, an investigation into his disappearance is currently ongoing. When mishaps have occurred on previous challenges, invariably due to equipment failure, the skippers usually have an on-board solution to hand.

If not, another skipper will often be in the vicinity and can come to the rescue. A good example is from an earlier Azores challenge, when Minke lost its rudder in mid-ocean and Duncan attempted to jury rig an alternative.

When this proved ineffective, George Arnison sailed to his assistance in his classic Dee 25, Good Report. In a remarkable feat of seamanship, the two skippers set up a system whereby they could tow under sail, safely making landfall 11 days later.

This endeavour was later recognised with a joint Seamanship Award from the Ocean Cruising Club. PBO enjoyed a tour of Minke the day before the start, with Duncan in good spirits and looking forward to his imminent retirement from a successful career as a yacht broker.

Minke, a proven long-range challenger, was in very good shape with all the equipment you’d expect for off-soundings voyaging. She had AIS, a PLB and EPIRB, as well as a satellite phone.

The main hatch had been modified for better visibility and watertight integrity, the engine controls moved away from spray infiltration, and a robust wind pilot self-steering vane graced the stern. An earlier design fault in the rudder (a small split pin that allowed the rudder to float up and out of its pintles) had been securely rectified.

With such a well-found boat, an experienced skipper, and benign conditions en route, the Jester community remains baffled as to what happened. The Marine Accident Investigation Branch is now investigating. Our thoughts go out to Duncan’s family and friends.

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This feature appeared in the October 2023 edition of Practical Boat Owner. For more articles like this, including DIY, money-saving advice, great boat projects, expert tips and ways to improve your boat’s performance, take out a magazine subscription to Britain’s best-selling boating magazine.

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