The Mille Miglia: Buckle up for an exhilarating grand tour

The Mille Miglia is a road race like no other, during which classic cars compete in a dash from Brescia to Rome and back. Matthew Bell went along for the ride

A Jaguar competing in the Mille Miglia (Patrick Gosling)

The train is more romantic. The plane gets you there quicker. But for the truly independent traveller, no form of transport offers more autonomy than the car. If you can square it with your eco-conscience, as a motorist, you have the freedom to choose your route. As the art critic Brian Sewell puts it: "You can opt to thrash down a German autobahn, or you can take your time along the back roads, stopping to visit churches and restaurants along the way."

In Italy, there are 26,000 churches and three times as many restaurants. There are also some of the most exciting roads in Europe, some clinging to the cliffs at Amalfi, others shooting, arrow-straight, down the plains of the Po valley. Nowhere is the decision over whether to press on or meander more difficult. Which is where the Mille Miglia comes in. What if you could do both at once? Race along country roads, but also take in the towns and villages? If only you could rattle through the cobbled centres of Florence and Rome, sampling local delicacies and admiring the churches, all from the leather passenger seat of an Alfa Romeo.

Well, you can. The Mille Miglia – literally, the thousand miles – is a demented and indulgent road race around Italy that happens once a year. It is the fulfilment of so many pleasures at once – speed, gluttony, bravado – all crammed into three days over a weekend in May. For the Italians, it is as culturally important as our London Marathon. Thousands upon thousands turn out to line the route, waving and cheering and holding up signs saying "Gas!", which means they want you to floor it, to show off the power of the car you're in. It is not for the faint-hearted. Indeed, the history of this event is chequered with tragedy.

Conceived in 1927 by a group of fearless young racing drivers in Brescia, a town in the foothills of the Alps, the Mille grew into an annual event that ran for 30 years. The loop was roughly the same: starting outside the duomo in Brescia, down to the east coast at Ferrara, south to Rome, then back up through the Po valley via Florence and Siena. This was the golden age of motorsport, and the Mille attracted all the big names: Stirling Moss, Juan Fangio, Tazio Nuvolari, all driving the fastest and most beautiful cars: Ferraris, Maseratis, gullwing Mercedes.

The speed and glamour and thrills were intoxicating, but the death rate was shocking. Each year, 600 cars would enter, of which maybe 200 would finish. Shop windows and street corners would end up littered with crashed cars, and over its 30-year history, 56 lives were lost. It culminated, in 1957, with an accident so horrendous and bloody that the event itself was killed off. A Ferrari driven by a Spaniard, Alfonso de Portago, flipped into a crowd, killing both team mates and nine spectators, of whom five were children.

So when the Mille was revived as an amateur event in 1987, it was reinvented not as a race, but a time trial. This means the skill lies in arriving on your correct second at various control points. But few people are here to win. They are here to soak up the unique chaos and romance of an event that could only really take place in Italy. For three days, a carnival-like atmosphere descends, as all the usual rules are turned upside down. Where else would you find policemen on motorbikes waving you through red lights and encouraging you to break the speed limit?

The snag is that you need a pretty special car to enter, not to mention the £8,000 entry fee (though every team is presented with two Chopard watches at the end). Only cars built between 1927 and 1957 are eligible, the years when the original event took place. Even if you are lucky enough to own such a car, getting an entry is not guaranteed. The event is over-subscribed by a factor of three, and the organisers have no compunction in awarding entries only to the cars they consider to be the finest. If you can prove your car competed in the original event, you're usually in.

Last year, a record 415 cars took part, and I was fortunate to be with them. Luxury car manufacturers such as Jaguar and Mercedes-Benz sometimes enter a team, and send along a fleet of their latest sports cars to join them. The finest cars in Italy in early summer – what could be better? Last year, our team consisted of six meticulously prepared Jaguars, three XK120s and three C-Types. Both models were built between 1948 and 1954, peak years of the Mille Miglia. They shared the same engine, the C-Type being simply a rarer racing version of the XK120. One, driven by Leslie Johnson, came fifth in the 1950 event, a remarkable achievement for a standard production car.

The people in our team were pretty high spec too. Among them was the chairman of Fox films, Jim Gianopulos (Titanic, Avatar), who collects old cars, and had persuaded Daniel Day-Lewis to join him in one. The models David Gandy and Yasmin Le Bon were also co-driving. Sir Chris Hoy, having given up cycling after his victories in the 2012 Olympics, was competing in a third car with Andy Wallace, a professional racing driver and winner of the 1988 Le Mans.

I had expected to be part of the support team, following behind in the new Jaguar sportscar, the F-Type. This was exciting enough, but imagine my joy when it emerged Sir Chris Hoy had been held up in Britain, and someone was needed to take his place. Andy Wallace would drive the first stage, and I was to be his navigator.

The route varies slightly every year, but the start line is always in Brescia. The mayor is a canny man. He allows the Mille to invade his town, on the condition that the event begins in the evening to give townsfolk the chance to wave the cars off after work. Judging by the thronged streets, they all do. However, it generates an unbelievable tension for competitors.

The hours leading up to the start are a period of feverish anticipation. The day before, all the cars are inspected and scrutineered in a giant hangar outside town. But on the day, because of the mayor's edict, there's nothing to do but hang around waiting for night to fall. Happily, Brescia is blessed with plenty of good restaurants, not to mention its magnificent Renaissance centre, with its arcaded squares and wedding-cake churches.

All the cars park up in the stone-paved streets, and look shiny and magnificent against this gracious backdrop. But as I counted the hours down to the start, I was in no mood for fine food or architecture. Our car, a race-prepared 1951 Jaguar XK120 open two-seater, had been meticulously rebuilt and prepared for the event. Andy Wallace is so professional a driver that he once achieved 240mph in a Maclaren F1 and survived. So, if anything was to go wrong, it wouldn't be the driver or the car letting the team down – it would be me.

Our arrival at the start line coincided with a rainstorm. This is normal for this part of Italy, even in May: Brescia sits high in the foothills of the Alps. It did nothing to dampen our spirits: if anything, it added to the excitement. As we waited in line for the 415 cars to set off at one-minute intervals, all revving their engines, it struck me that is was just as well that the people of Brescia are used to petrolheads. It was originally home to the Italian Grand Prix, pre-Monza, and gives its name to one of the earliest racing Bugattis.

Finally, after what felt like hours, it was our turn. We drove on to the start ramp, where the mayor introduces each car and its team to the crowds over a PA system. Daniel Day-Lewis and Yasmin Le Bon had received wild applause. Sir Chris Hoy was no less a star attraction, and the mayor had not had time to notice that my thighs are considerably smaller than those of an Olympic cyclist by the time he introduced us to the crowds. I nodded and smiled, and tried to look as Scottish and athletic as I could. But the mayor noticed just in time not to thrust the microphone into my face, and soon after eight o'clock, we were allowed to set off.

The next four hours were among the most enjoyable of my life. We set off east in torrential rain towards Verona and Vicenza. The organisers negotiate with all the towns along the way to allow cars to pass through normally pedestrianised city centres. There's nothing quite like sliding round the glistening cobbles of Renaissance piazzas in a 1950s Jaguar. All was going well until disaster struck. Neither of us had checked the fuel level before setting off and Andy soon spotted we had much less than we thought. Because the car was not ours, we didn't just pull over and fill up, but radioed the support team, who were keen to use their own fuel.

Amid the chaos, we had been separated from our support vehicle, some 15 minutes behind. So, we pulled up at a petrol station and waited. The lights of Bardolino glinted across Lake Garda, and roar by roar, we looked on as Bugattis and Ferraris flew by. Perhaps we lost 20 minutes. For a four-hour stage, it should be easy to recoup, we thought. But at every time control, we seemed to be behind. And so came the defining memory of that weekend. To make up time, we decided to join the motorway and get ahead. Andy put his foot down. A 1950s racing car doesn't bother with a windscreen, or a hood, and at high speed, it's quite hard to see through the wind and the G-force.

By the time we had skidded through the streets of Vincenza and into our destination for that night, Ferrara, at about midnight, we were back on track, and were winning within the Jaguar team. We slept well.

Sadly, Chris Hoy had arrived by now, and took over his place in the car. My consolation was the chance to drive the new F-Type Jaguar for two days solid through some of Italy's most exciting roads. Up the winding hairpins of San Marino, through the lush undulating hills of Umbria, down the Tiber valley to Rome.

The third and last day is the maddest and longest, covering almost 450 miles all in one go, including the gruelling Raticosa and Futa passes.

The rain returned as we pounded further north, and I still can't believe we got out of Bologna alive: we were racing through its soaking streets, slipping and sliding over brick and stone. It was dark by the time Brescia was in sight, and we reconvened, exhausted, jubilant, and bursting with stories to swap in the bar.

David Gandy and Yasmin Le Bon had run into a ditch and had to tape the front end of their car back together. DDL, as we now called him, had been swamped with autograph-hunters in most towns. All the cars were filthy, and of the 415 that set off, just 340 finished. Our positions in the final scoreboard are not worth recording, and the event was won by an Argentine crew in a 1927 Bugatti. It was all over so quickly, and so often I had wanted to stop and explore the towns we were rushing through. But the intensity stays with you, the rush of seeing 147 towns in 48 hours. Once the tiredness had lifted, we agreed that we could happily do it all over again.

And here lies the beauty of this event – as it takes place entirely on public roads, you don't actually have to enter to take part. Anyone with a map and a keen eye can follow the convoy: just turn up in your own car and see where they go. Which is how I plan to see it this year. I've bought a £50 plane ticket to Milan, and hired a Fiat Punto, and will be chasing the pack like a groupie. It may not be as glamorous as last year, but I have caught the bug, and can't stay away.

The next Mille Miglia takes place from 15 to 18 May (1000miglia.eu)