This page stands as a permanent memory and tribute to our fellow-Jester Challenger Duncan Lougee, lost at sea during the 2023 Jester Baltimore Challenge.

Duncan was a much-loved and highly respected member of the Jester Challenge community, having sailed in five Challenges over a fifteen year period. He sailed in our first ever Jester Azores Challenge in 2008 and our second full Jester Challenge to Newport, Rhode Island, in 2010, skippering his Rustler 31 Vaquero, although in the latter event he was forced to retire with mast problems. In 2015 sailed his Val 31 trimaran Aerodrama to Baltimore.
A yacht broker by profession, Duncan lived and breathed yachts, and it seemed that with his final vessel, the Varne Folkboat Minke, it was a case of love at first sight. In 2021 he sailed her in the Jester Azores Challenge, and it was during this voyage that he demonstrated his unflinching fortitude and seamanship. Minke lost her rudder in heavy weather with over 400 miles still to sail. Incredibly, he managed to sail the boat for several hundred miles with no rudder, before accepting a tow under sail from fellow Jester Challenger George Arnison in Good Report. In total, Minke and Good Report covered over 600 miles effecting this extraordinary self-rescue, of which 232 were under tow.
There is therefore an extra poignancy in the loss of Duncan on a relatively short passage in benign weather. We can never know exactly what happened, and speculation is pointless. All we know is that we have lost a fine sailor, a good friend and a real gentleman.
All the Jester Challengers salute Duncan on his final voyage.
Duncan had spent most of his life around boats. He was a qualified boatbuilder, had worked for a yacht charter company in the Caribbean, and having joined the East Coast Yacht Brokers Clarke and Carter, rose eventually to a directorship with the company. He was also a talented musician.
Here are Duncan’s own words about the first three Jester Challenges he sailed in, written for Ewen Southy-Tailyour’s ‘retirement book’.
The 2008 Jester Azores Challenge
I can’t remember exactly where or when I first heard about the Jester Challenge, I think it must have been one of Ewen’s magazine articles I was reading. Curious to find out more I fired off an email and quickly got a reply bubbling with infectious enthusiasm. At the time I had a totally unsuitable boat, so the first Jester in 2006 was out of the question. Sometime later, whilst looking for a Twister I fell in love with a Rustler 31, so had to ask Ewen for permission to use an ‘oversize’ boat. Another enthusiastic email in reply politely telling me to get on with it. So that was it; I entered the JAC08.
As all Jester Challengers will tell you, the difficult bit is not really the Challenge itself but preparing the boat and getting to the start line. Lots of late evenings after work all through the winter, antifouling in the snow (yes, really!), bank account drained, credit card maxed out and then a horrible delivery trip from my East Coast base to Plymouth – NE8 and heavy snow forced an unscheduled and expensive stop in Brighton. The doubts flooded in, what had I let myself in for?
Well, a jollier bunch of sailors would be hard to find and lasting friendships were made. Jester Challengers seem to be an eclectic mix of interesting characters, as diverse as their chosen boats are different in design. Ask half a dozen of them a serious marine question and you’ll get six different answers, all of which are right! And don’t be fooled into thinking us sad and lonesome singlehanders, we all enjoy a good party and look forward to the pre- (and apres!) Challenge socialising.
On a more serious note, we all have great respect for the sea and manage to prepare ourselves and our craft without any Rule Book or Health & Safety manual, just common sense and good seamanship and a healthy awareness of our own shortcomings. The first Jesters were treated by the marine press and other luminaries in the sailing fraternity as a bit of a joke, a dangerous joke, with warnings of future disasters likely to prove the point. The opposite has proved true, our safety record is extremely good and underlines every Challenger’s disdain for the ‘nanny state’. You don’t need rules to sail safely.
Having finally completed the Jester Azores Challenge in 2008, sailing up the River Orwell on the East Coast to my mooring – I don’t consider any voyage complete until you arrive back on your mooring – I felt tired, elated, happy, skint, wiser and very pleased that I’d been brave enough to take the plunge into the unknown.
The 2010 Jester Challenge
The JAC08 was secretly a warm-up for the big one, The Jester Challenge to Newport RI, USA. Having gained permission for time off for the Azores Challenge, it didn’t come as such a shock to my boss when two years later I asked for a three month sabbatical to take part in the JC10.
It is recommended that every Jester complete a singlehanded voyage of at least 500 miles to make sure that they, and their vessel, are suitably prepared. My own trial trip was to the Azores and back in 2008, so I felt confident that Vaquero and I were well prepared. However the route across the North Atlantic is an unforgiving one, so I went over everything with minute care and attention. I had a plan for every eventuality I could imagine, or so I thought. Once again my ‘oversize’ boat was allowed to take part by permission of the other skippers and I arrived in Plymouth in good time for the start allowing a relaxed approach to the final preparations.
Ewen started the Challenge as usual with both barrels of his shotgun and we all set off down Channel with a following breeze and a waft of Johnson’s Baby Powder (the ‘smoke’ from the starting gun). The favourable wind allowed us to get out into to the Atlantic with little fuss before we had to face our first headwinds. And then the wind went resolutely into the SW and rose in strength as expected and we all settled down to the long slog to America.
I was sending text messages home with position reports and general updates and reading back through them you can easily see when the weather was particularly rough or not too bad. Bad weather, brief position report only; not too bad weather and a bit of chat with it. The position on the chart crept slowly towards Newport. I would have a small celebration as the distance ticked off, usually by reaching some feature on my chart in an otherwise blank expanse; a coffee stain, a line of longitude and, most exciting, having to turn it over when I could then see my destination. All these warranted a slice of cake, or opening a fresh packet of biscuits or some other small reward.
I then noticed on my daily checks that the lower shrouds had gone a bit slack. Having tightened them up two days running I realised that something was amiss and choosing a relatively calm day I managed to climb the mast and have a close look. The bolt through the mast holding the lower shroud chainplates was slowly sawing its way downwards. If I couldn’t stop it the mast would eventually collapse. I’d reached the Grand Banks and had to make the decision to continue to windward or retire home via the Azores, a mainly downwind route.
After 24 hours I decided to retire and return home. A quick stop in the Azores allowed me to jury rig the mast and I got safely home and made repairs. Had I withdrawn that bolt before leaving I would probably have reached Newport. A lesson learned.
My Jester Challenge was over, but I vowed to try again. This was unfinished business.
Here’s a link to a short video about Duncan and his yacht made by yachting journalist Jake Kavanagh prior to the star of the 2010 Jester Challenge. This video shows Duncan’s exemplary attention to detail in his yacht preparation:
The 2015 Jester Baltimore Challenge
I had sold my Rustler 31 when I found this Val 31 for sale. A well proven design by Dick Newick it has been described as a day sailor with offshore capability, mainly due to Mike Birch’s achievement of coming 2nd in the 1976 OSTAR in his Val 31 Third Turtle. I’m not sure I have his ability but I felt the Baltimore Challenge would be achievable. And so it was I found myself once again on the Jester start line in Plymouth, this time headed for Ireland. And again this Challenge started with light winds and a waft of Johnson’s Baby Powder from Ewen’s starting gun. A third time I had to seek permission for an ‘oversize’ boat. After pointing out that the average length of the three hulls was 27ft I was politely told to ‘just get on with it, Duncan’.
With one other trimaran in the Challenge the competitive spirit kicked in and a mini race was on. The light airs do not favour these older designs and I was soundly beaten into Baltimore by a well sailed smaller tri. In many ways the Baltimore Challenge is a testing experience for a singlehander. The route is littered with Traffic Separation Schemes, fishing boats, challenging tides, rocky headlands, tricky sea conditions and often poor visibility, so achieving much sleep is difficult. On the plus side there is always nearby shelter if things go awry and the whole Challenge can be fitted into a normal summer holiday. But the destination is worth the effort. The welcoming hospitality is more than worth a few sleepless nights and the local Guinness is delicious. This was my third Jester Challenge, all three with a different destination, only two completed. Would I be brave enough to attempt the Azores or Atlantic with this trimaran. Not sure. It is now 2021 and I have been off the water for the last five years. There is another Jester Challenge to Newport planned for next year and I have decided that I cannot leave my unfinished business any longer. I have bought a little Folkboat and entered the Azores Challenge this summer, Covid allowing, as a warm-up for the big one next year. What is it that brings a small core of us Jesters back to this sailing adventure? The Covid pandemic has certainly made a lot of people take stock of our lives and revaluate their priorities, so maybe us Jesters are just ahead of the crowd. So here I am once again, older and greyer, steadfastly ignoring the lessons of experience, draining my bank account, maxing out the credit card and working all hours to get my Folkboat ready for the JAC21.
Some Short Tributes from Other Jester Challengers

‘I treasure this photo of Duncan and myself enjoying a relaxed meal a couple of days after we finally arrived in Praia da Vitoria, after the 2021 Jester Azores Challenge. It was a very happy moment…after an extremely uncertain and difficult nine days ‘together’ getting Minke back to safe harbour after she had lost her rudder in a mid-Atlantic gale.
I know Duncan feared that he would have to abandon Minke. But he showed both great strength of character to overcome the emotional shock of his dire situation, and then incredible seamanship to continue to sail the rudderless Minke just by balancing her sails – holding a straight line course through constant adjustments, for days on end, and in often rough conditions. It was a privilege to be able to help him, and sailing Good Report across the JAC’21 finish line with Minke – successfully completing both her self-rescue and our Jester Challenges – was one of the proudest moments of my life. Something that I will never forget.
Our conversations at sea were rather limited and very functional, so it was really good to be able to spend some time ashore with Duncan in the days after and to get to know him a bit better. I was so looking forward to catching up with him again over a pint in Baltimore in 2023 but tragically he never arrived. But I will always remember Duncan with huge affection, the deepest respect and very warm memories.’
George Arnison
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It was the autumn 2007 when I met Duncan for the first time.‘I only met Duncan briefly twice, once in Mayflower Marina just before the Azores Challenge in 2021 and again when I was considering buying a towed generator that he was selling on behalf of a friend. He was very knowledgeable and had a great deal of offshore sailing experience as well a love of classic boats. A tragic loss to the Jester Challenge and the sailing community as a whole. I wish I had got to know him better.’
Bernie Branfield
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It was the autumn 2007 when I met Duncan for the first time.
In fact there were 5 of us from the Essex / Suffolk area meeting for the first time that night at a Harvester Restaurant in Braintree just off the A120. I was later to call ourselves the 5 Amigos and would be surprised 17 years later that Duncan, George Jepps, Alan Charlton, Paul Feasey and myself would still be great friends and still meeting albeit less frequently. Such was the bond between Jester Challengers and in this case the 5 of us doing our first Azores Challenge the following year.
Duncan was clearly the most experienced of us having previously sailed in the Caribbean when working for a charter company for whom he had skippered boats for. Having just come from work he was wearing a Clarke and Carter Yacht Brokers jacket and I remember being somewhat comforted by the fact that we were in the presence of someone who knew a thing or two and would prove very useful in helping us ‘rookies’ who were doing an ocean passage for the first time. Having said that Duncan was one of the first to admit there was a big difference sailing the ocean on a fully crewed 40 footer versus single-handed in a small boat.
Duncan’s friendly nature meant he fitted perfectly into the group and it wasn’t long before wives and partners joined us making the 5 Amigos now 10. I recall meeting Louise, Duncan’s partner and now wife, for the first time. It was clear they were a good team each allowing the other to follow their passions in life, Duncan his sailing and Louise her love of horses. I was to learn later that Duncan was also an accomplished horseman and learned even later still accomplished at most things he tried his hand at including a successful yacht broker, motorcyclist, musician, and boat builder.
The 5 Amigos successfully made it to the start in Plymouth for the first Azores Challenge in 2008. Duncan being rather short on available holiday decided to sail his Rustler 31 Vacquero to Plymouth in one go. It was clearly a good example of seamanship, demonstrated even further by the photo he sent me showing his boat with her deck covered in snow.
Unsurprisingly Duncan was the first of us to arrive in the Azores. We were shortly to be joined by our wives and partners who unbeknown to us at the time had formed their own little support network in trying to cope with something they weren’t sure their other halves should be doing.
Duncan was the only one of us to go on to enter the 2010 Atlantic Challenge (I wasn’t to follow until 2014). It was here in Plymouth just before the start that I was invited to join Duncan, Louise and members of his family for dinner. I remember being instantly impressed with the closeness of the family. His brother Will and his wife had travelled from France where they lived and were joined by one of his sisters, Liz, who had moved some years ago from London to Dedham in Suffolk to be close to where Duncan and Louise had made their home. Duncan was the youngest of 5 children and clearly still the ‘baby brother’ of the family.
Most people who have sailed the Atlantic single-handed will tell you there are no easy years. However, 2010 did turn out to be one of more challenging years with most competitors at some point or other hard on the wind for prolonged periods, coupled with the odd force 9 – 10 gale. The 4 Amigos sitting at home following Duncan’s progress with great interest were all hugely disappointed when we learned he had turned around 3 quarters of the way across to head back to the Azores. There had clearly been a problem. We were to learn the long periods of sailing hard on the wind in big seas had caused the mast to weaken around the lower shrouds with the risk of the rig being lost. It was typical of Duncan to make the difficult but very seamanlike decision to turn around. It’s difficult to imagine his disappointment.
It was my turn to cross the Atlantic in 2014 and I remember Duncan making himself available in the background, always there when he was needed. As a yacht broker he was the perfect person to comment on the type of boat I had chosen and I remember sitting in Clarke and Carter at his desk whilst he passed his expert eye over the boat spec’, ticking ‘this’ and commenting on ‘that’.
It was unsurprising that he would be at Plymouth to see me off and it was my turn to introduce him to my family. Everyone remembers him as a very entertaining and likeable person. Typical of Duncan he gave me a bottle of champagne and an envelope to open when I reached halfway across. In some video footage I recorded when opening the champagne and card I joked to the camera that the card read he never thought I would get this far. In reality there was a slight choke in my throat that he congratulated me on getting halfway and willed me on to the finish.
Some months later Duncan was seeing me safely on to a pontoon at Fox’s Marina in Ipswich where I tied up for a few days upon my return home. My brother-in-law filmed my arrival which clearly shows Duncan in calm control of my mooring lines and the situation. He was one of the first to offer me huge congratulations.
My friendship with Duncan was to continue to grow over the years. In later years we would play music together on a Thursday evening in the spare bedroom of his cottage, he on piano, me trying to follow on flute. He was a very talented pianist and I’m sure my lack of timing drove him to distraction most of the time. I can still here him tapping his foot and counting 1 & 2 & 3…..It was rather fitting at the service celebrating his life that his nephew played Divenire by Ludovico Einaudi. It was a piece we both loved and on the odd occasion ‘pulled it off’. I have a recording on my phone of Duncan playing the solo piano piece to it, allowing me to practice at home on my own. I don’t have the courage to play it any longer but he was a very fine musician.
That is the Duncan Lougee I knew. He will be much remembered and much missed.
So lucky to have had but so sad to have lost a good friend.
Paul Mead
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‘Duncan epitomised the Jester spirit. He was meticulous in his preparations for sea-going, fearless and persistent as a sailor, and great company. I was particularly impressed by his handling of his 2021 Jester Azores Challenge emergency. To lose your rudder mid-ocean is a sailor’s nightmare. He refused to give up, and with a little help from his friends, brought Minke many hundreds of miles to Praia da Vitoria.’
Roger Taylor
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