Inside Mille Miglia: Italy's Grueling, Four-Day Vintage Car Race

“A man who has not been in Italy is always conscious of an inferiority,” observed Samuel Johnson, in 1776. The English writer was referring to the grand tour of Europe, then at its zenith. It was an elite finishing school of sorts for young men, and a handful of brave women of affluence, to be taken as a cultural education. The quote comes to mind driving alongside a frenzied convoy of racers in classic, priceless motor cars whilst tearing through the ancient city of Arezzo and around the medieval Piazza Grande square. We head south toward Cortona, the stunning village made famous by the novel Under the Tuscan Sun. Police on motorbikes escort our fleet, encouraging us through otherwise restricted areas, as racers revel in the freedom this event allows.

This is Mille Miglia, the most evocative classic car race in history, and positively the most Italian of all endurance tests. There are participants here from almost 50 countries—many are classic car aficionados; most are wealthy collectors. There are race car drivers taking part. Celebrities have come along too, including Guy Berryman from the English band Coldplay and the legendary Italian rock star Piero Pelù, both huge car enthusiasts.

The four-day race route, from May 16–19, honors the original map sketched in 1927 by two young counts, Aymo Maggi and Franco Mazzotti, their sports manager, Renzo Castagneto, and a motoring journalist by the name of Giovanni Canestrini. Evidently disheartened by the Italian Grand Prix’s move from their hometown of Brescia to Monza, they gathered a group of wealthy friends and promptly decided on their own race. The map was thus drawn from Brescia to Rome and back in a route resembling the figure eight, covering roughly 1500 km—1000 Roman miles—hence the name Mille Miglia.

Until 1957 it was an open-road gran Turismo motor car endurance test. It had a huge following and helped make grand touring specialists Alfa Romeo, Maserati, Ferrari, Mercedes-Benz, and BMW famous. Following a 20-year break, Mille Miglia was reborn in 1977 as a classic and vintage car race. Now, to be eligible for the competitive 450 or so slots, the cars need to have been created before 1957 and must have attended or be registered to the original race.

Despite the appearance of fun, this is a truly grueling race. The driving days are long—13 to 14 hours—and navigation is a three-volume analog logbook. There are strict rules to abide by: the race cars start every 20 seconds from around 6 AM, and speed limits are strategically placed en route to keep racers on their toes. We are here to observe the race. My copilot is a young racing driver who keeps me on constant alert as we swap between the two Alfa Romeos made available to us—the latest hot Giulia 2.9 V6 sedan and a compact performance SUV Stelvio 2.9 V6, both in flagship Quadrifoglio guise. These are fast and exciting cars, and the Giulia offers highly engaging driving dynamics, especially when on one occasion we veer off route in a bid to catch up with the race and end up on the old Roman rocky dirt road.

Mille Miglia offers a fantastic opportunity to see parts of Italy you may otherwise miss. On day one we head in the easterly direction from Brescia passing by Lake Garda, then south to Ferrara before finishing the day in Milano Marittima, a pretty seaside town on the Adriatic coast. It is on the second day when the true spirit of the race kicks in. A super early start takes us through San Marino heading southwest toward Rome as the skies open up, heavy rain drenching the many open-top race car roadsters. We arrive in Rome at sunset with a chaotic end to a long day, attempting to enter a hotel that clearly cannot accommodate so many cars and people.

I meet with Stefano Agazzi, Fiat and Alfa Romeo’s FCA Heritage collection manager. It is his 12th race, he says, admitting to, on occasion, resorting to imaginative solutions to rescue some of these old vintage automobiles. “In 2013, we had a one-off Sportive by Bertone driven by an Italian journalist who had forgotten to switch off the lights in the parking lot and the battery was completely out,” he smiles. “We finished the last 50 km holding a torch outside the window.” He says all the drivers are trained to be able to handle some of the vehicles that are more than 80 years old as, naturally, prewar cars require a different skill set. “Our target is to come back with a car completely working,” he muses.

The most scenic stretch is on the third day through the stunning roads that cut into the heart of Tuscany, lush and green from the frequent spring downfalls and blossoming poppies. In Siena, the whole city has gathered to greet us. A young boy offers us fresh bread as we drive around Piazza del Campo.

Heading west, we pass through Lucca and onto Parma, stopping off at the historic Monza racetrack on the final day before finishing back in Brescia in time for a grand party to celebrate the winning Alfa Romeo team. This classic Italian marque takes the top three trophies in a 1933 6C 1500 Gran Sport Testa Fissa, a 6C 1500 Super Sport from 1928, and 1929 6C 1750 Zagato—all museum pieces from the newly refurbished Museo Storico Alfa Romeo in Arese.

Marcus Ericsson and Charles Leclerc, the drivers of the Alfa Romeo Sauber F1 Team, join the race toward the finish line, in a 1932 Gran Premio Tipo B and a 1955 750 Competizione. The company has recently returned to motor racing and the occasion plays well in communicating the message. “This race is fundamental for our brand building. It helps us revisit our history and offers a platform for presenting our new models,” explains the FCA Heritage marketing and communications manager, Gianfranco Gentile. This year’s race coincides with the 90th anniversary of the first of the 11 victories for Alfa Romeo, recorded from 1927 to 1957, making the carmaker the overall champion. Mille Miglia, though, isn’t entirely about the win. It is an ode to the glorious golden age of the automobile. “This is a big celebration of Italian culture, the Italian landscape, the scenery, the architecture, the beauty that characterizes our country,” says Gentile. “It is a unique opportunity to see Italy in four days.”