"So, which one shall we take?" If you happen to love cars, as I do, the question is enough to blow a mental fuse. How, exactly, am I supposed to choose between these seven cars? Under what circumstances do you decline possibly your only-ever opportunity to ride in a Porsche 911 2.7RS, the greatest road-going 911? How do you make a meaningful comparison between a pre-war Aston Martin Ulster, one of just 31 made, and a priceless 1955 Ferrari 750 Monza sports-racer, also one of just 31, and decide which is the more significant, and likely to provide the greater thrill?

Chopard Mille Miglia car collection
Matt Sills

The question is a bit easier for Karl-Friedrich Scheufele, co-President of Chopard. They're his cars, and we're standing in his garage at his home in the Vaud countryside outside Geneva. He hints that this is not the complete collection. Among others, he mentions a Ferrari 275GTB/4 and a Gullwing Mercedes not present that day that would probably have caused me to pass out had they been part of my dilemma. Karl-Friedrich's daily dilemma is made easier by the fact that he has owned many of these cars for a very long time: thirty years, in some cases. And he drives them all regularly. His staff report that they can often hear him approaching Chopard's headquarters in nearby Meyrin in something old and noisy, which must be good for productivity.

Chopard Mille Miglia car collection
Matt Sills

I'd come here to answer a different question. Prior to 1988, Chopard had no association with motor sport. Chopard chronographs weren't used to time laps back when lap timing was still done on chronographs. Yet now, there are racing drivers I know who buy and wear a Chopard because they feel that the brand is a legitimate part of their world. The depth and authenticity of Chopard's association with cars and racing isn't quite on a par with Heuer's, say. But it isn't far off.

Chopard Mille Miglia car collection
Matt Sills

A thousand miles to Brescia

It comes from Chopard's long-association with the Mille Miglia, arguably the most exciting, exclusive event in the high-end global classic-car season. The original Mille Miglia ran – on and off – for thirty years between 1927 and 1957; a race over a thousand miles on public roads, starting and finishing in Brescia and looping through Rome and Florence. It broke cars and drivers; fewer than half of the hundreds who started each year would finish. “In my opinion, the Mille Miglia was an epoch-making event,” said Enzo Ferrari. “The Miglia created our cars and the Italian automobile industry.”

Chopard Mille Miglia car collection
Matt Sils
Chopard Mille Miglia car collection
Matt Sils

In 1977 it was resurrected as a "historic rally", open to cars that could have competed in the original event. Every year at least 2000 of the world’s wealthiest car collectors apply for just 375 places. And while the organizers stress that it isn’t a race, I can tell you that it is. I have competed in it twice, driving an ex-Stirling Moss Jaguar XK120.

It is insane. It is a convoy of the world’s most valuable, least-replaceable classic cars, often driven flat-out on open public roads, all actively encouraged by the local police, who even compete themselves. You get a couple of hours’ sleep each night and spend all three days in constant fear of wiping out a piece of automotive history or trying to figure out the rules, which the organizers make utterly incomprehensible.They call it the most beautiful race in the world: la corsa piu bella del mondo - but it's also immensely tough.

Chopard Mille Miglia car collection
Matt Sils

Chopard has sponsored the Mille since 1988, producing a limited-edition watch for competitors each year. At motor shows and races and the other high-end classic car events around the world, you'll glimpse Chopard Mille Miglia competitor's watches on the wrists of ex-Formula One drivers, superstar car designers and CEOs of global car companies. Chopard has official ambassadors, such as racing legend Jacky Ickx. But every year in the Mille it recruits another few hundred unofficial but very influential ambassadors who wear their watch as a badge of honour and a sign of a shared experience. I'm lucky enough to have two, from 2008 and 2012, and every time I wear them I'm reminded of a sleepless, gruelling, glorious weekend in Italy.

"It has become a world-wide community," Scheufele agrees, "and still an exclusive community in a way. When you wear one of the participant watches, you have really done something to earn it."

On the road

The longevity of Chopard's association with the Mille alone doesn't explain why it has become such an integral part of this world. I get the full answer in the first 20 metres of our drive. In order to prevent mental collapse, I asked Karl-Friedrich if we could take his 1929 Bentley 4.5-litre. I reasoned that the visual drama of the car's liner-like prow and chest-height, dinner-plate sized front lamps might make for more spectacle. And I secretly wanted to see how Karl-Friedrich coped with the truculent mechanicals of an 86 year-old sports car, with its crash gearbox and pedal layout with the accelerator in the middle.

Chopard Mille Miglia car collection
Matt Sills

But he has owned this car for twenty years, and raced it in the Mille Miglia. He jumps in and threads it out of the driveway and towards a favourite lakeside cafe with the ease with which you or I would drive a Ford Focus. You've heard about the wealthy car collectors who buy up these fast-appreciating assets, but can't drive them? Karl-Friedrich Scheufele is not one of those.

"As a boy, of course, cars came before watches," he says, happily holding a conversation despite the physical effort of driving a car like this. "My first was a Porsche 356 that was so full of holes that it couldn't be saved, and I had to wait a while before I could get another. That next one (a now-immaculate, rare Speedster) was also full of holes, but we were able to put it right, and I still have it."

Chopard Mille Miglia car collection
Matt Sills

Karl-Friedrich's father, Karl, bought the business from the Chopard family in 1963, and his son joined in his early twenties, becoming a vice-President in 1985, along with his sister Caroline. The deal to sponsor the Mille Miglia came soon after.

"I remember at the very early stages I had to really defend the idea, even within our company, within the family. It was not the opportunist thing to do. Nobody else was doing it at that moment. 'Why do we need to sponsor car rallies?' my father said, even though he was a car enthusiast. 'What is this Mille Miglia? Do we really need to do that?' Until he first went himself... He has come back every year since."

Chopard Mille Miglia car collection
Matt Sills

Car engines, watch engines

It is a spectacular day by the shores of Lake Geneva: cool and clear and perfect for driving. We reach the cafe, and he parks the beautiful, brutal Bentley as you might a bicycle. We take a table with a view of the lake and order coffee. Can he quantify how important the association with the race has been to Chopard?

Chopard Mille Miglia car collection
Matt Sills

"I think it put us on the map in the world of gents watches, and sports watches in particular. It really helped to establish us there. Now, if we take all our 'classic racing' models – the Mille Miglia, the Grand Prix de Monaco Historique, and the Superfast – these account for roughly 15,000 pieces out of about 80,000 each year, and watches account for about 65 per cent of our turnover."

So it has been a commercial success, but one based, as his piloting of his Bentley proves, on the credibility of the man and the motivation behind it. But I was surprised to hear that the influence of the Mille Miglia and classic motoring on Scheufele's approach to watchmaking runs even deeper.

"It also triggered the whole LUC idea in me," he says of Chopard's in-house haute horlogerie watches, named after the firm's founder, Louis-Ulysse Chopard, for which Scheufele opened the brand's specialist manufacture in 1996. "It encouraged that level of authenticity, and a wish to make Chopard an authentic brand in that respect. The discovery of these classic cars and their mechanical nature helped me along the way with the mechanical watchmaking."

Chopard Mille Miglia car collection
Matt Sills

That desire to make his own "engines", prompted by the Mille Miglia, has now come full circle. In 2008 Chopard established another factory, Fleurier Ebauches, to make in-house movements for its more mainstream models. The new movements made their debut in the Superfast collection, and this year the 01.01-C and 01.08-C appear in the three-handed Mille Miglia watches for the first time. Karl-Friedrich is wearing one: the Power Control with a "fuel gauge" indicating how much of its 60-hour power reserve remains.

Chopard Mille Miglia car collection
Matt Sills

I'm wearing my 2008 GT-XL competitor's chronograph, with a serial number to match my race number that year. We swap. Luckily, mine is just back from a service at Chopard and looking acceptable. Karl-Friedrich's new model is the usual perfectly-judged Mille Miglia balance of retro and modern: big and striking but wearable and not bling, with a deep, beautifully-finished case and the traditional tyre-tread rubber strap close-fitted to the case. The in-house movement is revealed through the case-back.

Chopard Mille Miglia car collection
Matt Sills

They always feel special, these things. Especially if you've earned yours on the Mille. And now, a little more so because it has Chopard's own movement. It makes me doubly miserable that I won't be driving this year: although you can, of course, just go and buy the watch, and for a price not over-inflated by the inclusion of an in-house movement.

Chopard Mille Miglia car collection
Matt Sills

Chopard has other sponsorship deals, of course. Karl-Friedrich's sister Caroline looks after its association within Cannes and even redesigned the Palme d'Or. In 2002 Chopard became a sponsor of the Grand Prix de Monaco Historique, an incredible weekend of vintage racing for which Chopard produces a range of watches.

But it is Karl-Friedrich's latest sponsorship decision that really proves his credentials as a car guy: more even than that super-discerning collection of sports cars back in the garage. He wanted a modern motor sport association. He could just have done yet another watch deal with a Formula One team or driver. Instead he chose to back Porsche's return to top-level endurance racing, a branch of the sport that doesn't get one per cent of F1's media exposure. The coverage may be less, but the significance of Porsche's return to a sport that it once dominated with some of the most charismatic racing cars ever to turn a wheel is well-understood by Scheufele's fellow car guys. And the technology with which the 919 Hybrid is laden speaks well to a watchmaker that now builds its own engines.

"This is the decision of somebody who is genuinely excited about Porsche," he says. "Second, my long-term friendship with Jacky Ickx (who won Le Mans for Porsche) also played a role. Third, I think it's the closest thing in modern motorsport to what we call classic racing. It's still a classic approach. And of course, technology-wise, it's amazing. It's really in the forefront of development. But for me, it's about Porsche first. Porsche was my first love."

Snap – two classic Bentleys

We finish our coffees by the lake and go back to the roadside to take the Bentley home. You can't calculate the odds against what we saw as we emerged. Having picked the ancient Bentley partly as the car most likely to shock the locals, we find another one parked next to ours: a 3.5-litre of the same vintage and a similar priceless value, the relaxed owner nowhere in sight, and probably having a quiet coffee, just as we were. Scheufele laughs, and bounds over to inspect it. "Incredible! I promise I didn't make this happen. What are the chances?"

Chopard Mille Miglia car collection
Matt Sills

The chances are maybe a little better in the Vaud than elsewhere, and a lot better if you're the kind of guy who drives a 1930s racing Bentley to get coffee.

Chopard Mille Miglia car collection
Matt Sills

Some more pictures from Karl-Friedrich Scheufele's garage

Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills
Chopard Mille Miglia car collection
Matt Sills