I’m trying to get a feel for the Jester Challenge, the solo event (one mustn’t say race) across the Atlantic to Newport. This staunchly amateur venture is unique in that it has a size range of 20-30ft, a start date and ports of departure and arrival but not much else.

What it positively does not have is a race organisation, a notice of race or an entry fee. So although there are 89 boats and skippers on the list of entrants, no-one knows until the skippers’ briefing on Friday how many will turn up or take part. It could be 40 or 60 or more.

Former Royal Marine and Yachtsman of the Year Ewen Southby-Tailyour founded the Jester Challenge for small boat sailors who had been squeezed out of the big races.

When the OSTAR disallowed boats of under 30ft it effectively disenfranchised the small boats that had begun the event – four of the five boats in 1960 were 26ft or under. Southby-Tailyour’s motivation was to “give back a race to boats under 30ft.”

So what you have is the diametric opposite of almost every oceanic race anywhere else in the world. Most of the boats are simple and low cost and their skippers disinterested in publicity.

But word has got round, and since the last transatlantic Jester Challenge in 2006, some sailors have actually bought a suitable nutshell in order to take part. “I think,” says Southby-Tailyour, “small boats are chosen by people as much because of the concept as the cost, although some people can’t afford anything else.”

Looking through Yachting World eyes, an event like the Mini Transat seems extreme. Fuggedaboutit. This is properly hardcore.

Meet Roger Taylor (pictured above), skipper and owner of MingMing. His boat is a Corribbee 21, a type of coastal cruiser you could, if you so wished, pick up for around £2,000. Roger modified MingMing to take part in the Jester Challenge four years ago and has twice sailed to the icy waters of Jan Mayen since.

She is junk-rigged and as pure a concept boat as any you’d see in professional hands. There’s a place for the windvane, the drogues, a little wooden bowsprit, two sculls to use for everything from emergency steering to jury rig spar, two sweeps for calms and a place for everything.

When I talked to him today, Roger had just finished provisioning his boat for 100 days at sea. Quite where he put all the food and water I don’t know. I asked if the boat was down a wee bit on her marks and he just laughed and said he’d repainted the waterline.

I also met Roger Fitzgerald, who bought his boat a couple of years ago. He’d been on a caravan holiday with his wife and came across an old copy of Practical Boat Owner, in which the Jester Challenge was reported.

He’d had a boat 25 years earlier, which he had been forced to sell when, as a mining equipment supplier, the business finished. He gave up sailing and took up bowls instead.

But on reading about the Jester Challenge, Roger said to his wife “I think I could do that.”

“She said: ‘Well, go and do it then,'” he tells me. That was in August. By September Roger had bought Ella Trout 3, a Dehler 29 and was on his way.

I should add, just in passing, that Roger is 73. 

The feeling I’m getting is that the Jester Challenge is a bit of a cult for people who couldn’t care less about cults, or trends or fashions or public profile or sponsorship.

The racing world and its rock stars are like alien life rumoured to exist in some distant galaxy. Some of the Jester Challenge sailors I spoke to today regard all that with deep suspicion and disapproval…the money, the self-regard, the sheer bloody extravagance of it all.

It’s brilliant. It’s pure journalist heaven, too, because there are more fantastic true stories here than you could ever wish for. But enough for now. I’m off to a drinks party on Ewen Southby-Tailyour’s gaffer.

Ewen has been given a case of Plymouth Gin – the Jester Challenge’s sole sponsorship deal – and I daren’t be late. Because judging by the wine that went out like the tide at lunchtime, it won’t last long.