Driving the Mille Miglia in a Mercedes-Benz 300SL Gullwing Is Like Freebasing Italy

While it's not quite the Hope Diamond of the collector-car world, a 1955 Mercedes-Benz 300SL is certainly a museum-worthy jewel. It's known best as the Gullwing for its winged doors, and I'd never even plopped into one until I went to Italy to drive one in the modern Mille Miglia. I suppose modern is an unnecessary adjective since time travel continues to elude me.

A re-creation of the 1000-mile race held from 1927 to 1957, today's Mille Miglia is open only to car models that competed in the original. So, if you have an Austin Healey 100/6 or a Peugeot 403 in the garage, you can apply to enter, but it's much easier to get in if you have the actual Gullwing that finished fifth in the '55 race. That'd be my ride for the first day of the race.

When it's not out reliving history, this particular SL spends most of its days at the Mercedes-Benz Museum in Stuttgart, Germany. Piloted by racer and car designer John Fitch, this 300SL finished higher than any other stock car. That year proved to be an especially historic year as Sir Stirling Moss won it by driving at an average speed of nearly 100 mph in a Mercedes SLR, essentially a 300SL with the powertrain of a period Formula 1 car.

So what if I only crested 100 mph a couple of times on the roughly 200-mile route from Brescia in the north to Cervia—Milano Marittima on the Adriatic? My co-driver and navigator, German race-car driver Ellen Lohr, who lit up the German Touring Car series in the '90s and continues to chase checkered flags today, goaded me to hammer the 67-year-old SL like one might hammer a Nissan Sentra rental. So I did. Four gears, 240 horsepower, eight-figure value, no brakes, lots of traffic, summer heat, all against an Apennine background.

The route passed through tiny villages filled with locals who turned out to see, hear, and smell history. "Give them some revs," encouraged Lohr. This traveling show included fleets of Porsche 356s and Jaguar XK120s dicing with Ferraris and Alfa Romeos, plus surprises like three Chryslers: a '28, a '29, and a '53. In all, more than 350 vintage cars turned up to make noise and to make an already beautiful place even more beautiful.

This year marked Lohr's sixth Mille, and she expressed some surprise that an American could adapt so quickly to the Italian style of driving. Every Italian appears to be a frustrated F1 racer, and every trip is a qualifying lap. I suffer the same delusion of grandeur, so driving aggressively but also thoughtfully comes easy. Lohr kept the water and wafer cookies within reach, and her coaching included slapping my forearm whenever I'd grab the inside of the steering wheel to make it easier to turn the unassisted steering. A pair of driving gloves helped, a sentence I never thought I'd write.