On a cloudy midsummer afternoon, my best friend, Harry Scott, and I waved goodbye to our worried mothers and sailed out of Falmouth’s Carrick Roads – two naïve 20-year-olds, wide-eyed and open to the world. We had loaded Flying Cloud, my 22ft Clyst Class wooden sloop, with surfboards, a foldaway bicycle, two pasties each and a pint of milk, and set sail for Brittany looking for nothing more than an adventure.

Having graduated from university, we had no commitments to work or education, and the freedom was overwhelming. And what better way to travel than a small sailing boat? We were transients, able to make a home wherever we dropped anchor – ever sure of a warm bed and a hot meal.

Our arrival in France was a novel occurrence, for both us and the people we met. With every stop, people were taken aback at the sight of two Cornish boys in a tiny wooden boat.

We headed south down the Atlantic coast and by September, we were cruising west along the rugged, green and foggy northern coast of Spain. We were welcomed in the smallest fishing harbours, our long mooring lines fixed to the tall granite harbour walls. The friendly harbour authorities would come by and ask for nothing more than our names, then invite us to make use of the facilities and stop for a drink at the local Club Nautico.

In Portugal, the lush scenery was replaced with a flat, arid landscape. Brightly painted houses lay behind rocky cliffs and long sandy beaches. We poled out the jib and embraced the Portuguese tradewinds, goose-winging our way to Lisbon. Here we made friends not with the locals, but with a motley group of single-handed yachtsmen, who were all, like us, bound for the Caribbean for the winter. We were living the same dream – and we were doing it on a shoestring.

Then Harry jumped ship and joined up with a girl who had a van. In Lisbon he moved his possessions from Flying Cloud’s modest saloon into his new lover’s comparatively spacious 1997 Vauxhall Arena. It was an emotional goodbye, and initially I felt lonely and slightly dispirited at the thought of no longer having my best friend around to share conversation and boost morale. Also, on a practical level, it meant I would be unable to leave the helm when underway. So Harry was replaced with a bungee attached to the tiller – the ultimate short-term self-steering system.

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My inspiration to continue sailing came from Flying Cloud’s library, which contained an array of works by influential adventurers: Chris Bonington, Tristan Jones, John Guzzwell, Shane Acton, Yossi Ghinsberg, Laurie Lee, Sir Robin Knox-Johnston and Bernard Moitessier. Dreams of adventure occupied my thoughts; I yearned for adventures of my own.

The imperfect vessel

Flying Cloud is a strong and capable little yacht. Her decks had been sheathed in epoxy, and she had a relatively modern aluminium rig and single cylinder Yanmar engine. But there were still three very important additions I needed to make before sailing across the Atlantic: self-steering; a sprayhood; and drainage in the cockpit.

I had always believed modern sprayhoods looked tacky on classic yachts and for a long time I rejected the idea of getting one. But every time solid water cascaded over the cabin top, which happened quite a lot, a hose-like stream shot down from under the sliding hatch and soaked the inside of the cabin. Keith Buchanan from Rat Island Sailboat Company, based on the Isles of Scilly, put together a canvas sprayhood, which fitted nicely over my sliding hatch.

I also covered the cockpit footwell with plywood and made two drain holes through the transom. It wasn’t totally self-draining, but it was a lot better than before.

Lastly, my stepfather, Dave Cockwell, who happens to be a master shipwright, and I created a series of drawings for a bespoke self-steering system. It was loosely based the design by Blondie Hasler, the man who founded the OSTAR in 1960, where the wind vane turns the trim tab, and the flow of water past the tab causes it to swing in the opposite direction, altering the course of the yacht.

Apart from the wooden vane and nylon bearings, everything was made from stainless steel. There were no wires or lines and no possibility of wear.

I sailed round to the Rio Guadiana, the turbid, meandering river that separates the south of Portugal from Spain, and finally finished building the self-steering moored among the community of British expats in between the Spanish village of San Lucar and the Portuguese village of Alcoutim.

I was making plans to leave, when a big low moved over the Algarve bringing three days of torrential rain. The water level quickly rose in the river and the current doubled in strength. One night, a southerly gale blew up in opposition to the river current and Flying Cloud swung around on her anchor chain like a wrecking ball. A big, saturated log, which must have rolled downstream along the river bed, managed to wrap itself three times around my anchor chain.

After a long struggle to free the boat, I motored back down river, weaving my way between extensive bamboo rafts, garden sheds, and bits of homemade pontoon, finally ghosting out from behind the breakwater and back into the comparatively clean and clear sea water of the Algarve.

In a westerly Force 3, I headed south-west and tried the self-steering, watching anxiously as my contraption took command. As Flying Cloud began to head up, the wind vane detected the change in direction and pushed on the trim-tab tiller, which shifted to starboard bringing her back on course. I was ready for the Atlantic.