The man who pays his way

Namibia's far south-west is the crumpled brow of Africa. Five million years' worth of weather has created the world's biggest corrugation of sand dunes. Each day, truckloads of travellers breeze along to the foot of Dune 45, so called because it is (nearly) 45km along the road from the national park entrance. They scamper up the shifting sands to trample along its elegant crest. By the next morning the scars have been gently erased by the breeze. By then the overlanders are waking far away after another night under canvas.

"Not Your Everyday Journey," reads the slogan on the side of every Dragoman overland truck. Proof begins with the vehicle itself. The firm's corporate colours are white and an orange that is several shades less intense than the ultra-citric easyJet tone; I'd call it "Sainsbury's orange" – which is appropriate because some of the vehicles began life shuttling refrigerated goods around East Anglia for the supermarket chain. Dragoman is based on a farm in Suffolk, and sources its trucks locally for adventures that last up to eight months.

At Camp Green, Dragoman's HQ outside the village of Debenham, the trucks are converted from groceries to globetrotting while new recruits are converted from normal people to the demi-gods who act as tour leaders. Men and women are trained in an impressive range of skills. They learn to drive along some of the world's worst roads ("It's really important to get you off the beaten track," says company founder Charlie Hopkinson) and to defuse tension when the social harmony aboard the truck breaks down and the Brits square up against the Aussies. On the trip that occupied a three-week slab of my summer, the international peacekeeping skills of the leaders were not needed.

As with families, you can't choose your travelling companions, but Dragoman does what it can to ensure that there's a sporting chance of harmony by managing expectations.

"You will need to be fit enough to help every day with the camp chores (cooking, washing up, general camp set up) as well as putting up and taking down your own tent," the trip notes stipulate. To emphasise that this is not your everyday holiday: "You will be assigned a truck job, which could be collecting water and firewood, sweeping out the truck, loading the back locker, etc." Not quite "Slackers need not apply", but not far off.

Truck off – and why

The business of overland travel looks as tough as the trucks, which explains the business model that Dragoman and its rivals use. On most trips a "kitty" system operates. Everyone chips in a specified number of dollars for a group fund that covers campsite fees and meals, hotel stays, national park admission fees and local guides. In other words, exactly the marginal costs of the trip. Your initial payment to the company covers only the fixed costs of providing a truck, staffing it and fuelling it for the prescribed journey. Oh, and a small element of profit.

In this precarious business, any surplus can quickly be eroded. Which is why participants are told to bring along $400 as a "Contingency Emergency Fund" to cover war, flood or general pestilence that requires the whole group to fly over the afflicted area.

No contingency fund can help cover Dragoman's current local difficulty at a port in South America. A newly converted truck was despatched by ship to operate trips from the Andes to the Amazon, but has been impounded by customs officials for the past four years. Charlie Hopkinson says if anyone can extract the truck from the bureaucratic limbo, they can keep it.

Khartoum characters

In overloading history, the past is another country – but thanks to some forensic research by one of the pioneers, Gerald Davis, it can be mapped. Mr Davis has written Faraway Places with Strange Sounding Names – the Penn Overland Story, which chronicles the birth of the industry and reveals that the business of filling a truck with travellers was a spawned not by the Seventies, nor even the Sixties, but the Fifties.

Unless anyone can provide more accurate carbon dating, I am persuaded that the industry began late in the evening of 17 August 1959. The first England-to-Ceylon brochure promised: "1st Day – Depart from Dover on the night ferry to Dunkirk". The participants were told "55 Days allowed for Tour", for a price of £78 – the equivalent of about £1,600 today.

Overlanding was almost bankrupted at birth before it began, says Mr Davis: "Penn lost half the bookings when an unscrupulous agent in Charing Cross flew off to Australia with their clients' final payments." Most participants were buying transport to present-day Sri Lanka, whence they could sail onwards to Asia and Australia, rather than an adventure. But the trip included plenty of tourism – much of which was more achievable then than now. As well as time allotted for sightseeing in Paris, Venice and Istanbul, by early September they could enjoy the sights of Tehran and Isfahan in Iran.

The bus made it to Colombo ahead of schedule, in six weeks flat. Penn's pioneering trip to Africa was not so lucky. A Daily Herald headline read "18 people in bus riddle" above a report that: "The first London-Capetown overland tourist bus, carrying 18 people, was 'several days overdue' in the vast, burning desert scrubland of the Sudan last night." It turned out to be what today's travel industry would call "operational difficulties". A few days later everyone turned up safe and well in Khartoum – including "a Danish hitch-hiker picked up last week".

One of the world's all-time great lifts.