I Raced the 1000 Miglia in a $15 Million Mercedes-Benz

There's car racing, and then there is the 1000 Miglia. The 2200-kilometer route, all in Italy, is designed as a regularity challenge, testing navigation, precision and the mechanics of hundreds of millions of dollars of classic and antique automobiles.

Mercedes-Benz Heritage, the division of the global automaker responsible for upholding and preserving the heritage of the company, invited me along as co-pilot and navigator in the 2024 edition of the Mille Miglia, held last week. I jumped at the opportunity.

I'd never done the Italian race before, but I had done two previous iterations of the Mille Miglia Warm Up USA, the training program and competition held annually in the Washington, D.C. area, so I had an idea of what I was getting myself into.

The race is divided into four simultaneous challenges, all of which carry penalty points for being even a moment or meter off the set mark: navigation, arrival/departure time, average speed and varied time-distance.

This year's five-day race left Brescia on the first day and headed through Bergame, Novara and Verecilli, before ending in Turin. The second stage went through Genoa and along the Tyrrhenian coast to Viareggaio.

Rome was the third day's destination. On the fourth day, the 1000 Miglia route passed through Orvieto, Solomeo, Siena, Prato, Futa and Raticosa.

The fifth and final route took the vehicles from outside Bologna through Ferrara, Bovolone and Villafranca, winding around Lake Garda, and finishing in Viale Venezia.

Mille Miglia rules do not allow just any car to participate. Only vehicles whose models took part in the original 1000 Miglia races between 1927 and 1957 are allowed to start, and not all of them finish.

For the Italian adventure, I was paired up with the Marcus Breitschwerdt, CEO of Mercedes-Benz Heritage, in a 1930 Mercedes-Benz Super Sport Cabriolet valued by a company spokesperson to be worth $10-15 million. Last year, Breitschwerdt told Robb Report that he wouldn't let it go for under $25 million.

The car was originally commissioned for the last ruling Maharaja of Kashmir, Hari Singh, who specified the flagship model to match his yacht. Today, it calls the Mercedes company collection in Stuttgart, Germany, home.

The right-hand drive model has a four-gear (plus reverse) asynchronous gearbox that makes double-clutch operations a necessity. Its gas and brake pedal are in a reverse order than today's cars, with the gas in the middle and the brake on the far right.

The top of the shifter sat at about the same height as my knee, rising off the floor.

The Mercedes support team, complete with two experts in Pre-War vehicle mechanics, covered the rear seats, storing underneath a cooler full of snacks and beverages for the road.

Lunch breaks are scheduled, but there's no guarantee you'll have time to eat depending on the way the race goes. And, each team is running on about four to five hours of sleep per night, assuming they slept well, as each day 15-18 hours of racing occurred.

As navigator to Breitschwerdt's driver, I was handed a daily route book that included vague directions of the race next to approximate kilometer markers where turns and obstacles were located.

Having done the Warm Ups, I knew a few tricks to ease the process of navigating. Still, the challenge of having a vehicle that did not have tenths of a kilometer on the odometer, like most cars of its era, proved quite the obstacle. The 1000 Miglia team had foreseen this, and at some turns placed red arrows to show teams where to go.

I also hadn't raced with Breitschwerdt before. We didn't know each other's patterns and habits, and couldn't read what the other was thinking like you can with a longtime partner.

On top of that, the car was new to half of the duo and carried considerable weight from its 7.1-liter engine, which made acceleration, braking and pacing a challenge.

There are no seatbelts in the SS and both seats are loveseat-sized leather benches, with the rear sitting a bit higher than the front.

Despite this, and the aging mechanics below the floor, the car was surprisingly comfortable to ride in for hours on end. Over speed bumps one could get quite the lift when taken at a good pace. Little braided leather handles placed throughout the cabin could be used to hang on, but thanks to Breitschwerdt's driving expertise, I never felt like I needed them.

The long wheelbase of the model and effort-intensive steering meant that typical roundabout routes were not ideal. Instead, Breitschwerdt cut the roundness as much as possible, allowing for a straighter path to exit.

One thing I had not anticipated was how much the Carabinieri, Italy's military entrusted with policing duties, aided our travel. They kept the roads mostly clear, getting modern vehicles to slow or move off the side of the road so racers, who had less braking and acceleration power, were able to pass. They, and numerous volunteers along the way, blocked intersections so we wouldn't have to stop, and held up roundabout traffic so we could ride in with the coast clear.

Most of the local speed cameras were turned off or inoperable, which also helped the cause.

As we wound in and out of small towns, traversing the countryside and navigating up and down mountains, the crowds of people ebbed and flowed. In some places, none. In others, farmers on their tractors, groups of school children on a study break, and work-from-home-rs gathered to cheer and take photos.

In the town of Colombare, Italy, the streets were lined with spectators on the way to the end of the peninsula's castle, cheering and waving flags and hands. Driving along the shore of Saló, Italy, revealed crowds so thick the drive became more like a very slow procession as café patrons who had magnums of champagne on order chatted with the drivers passing by and grabbed photos with them.

Children held out their hands asking for high-fives and all along the route and older Italians sat in their gate doorways watching, waving and smiling as the cars passed.

The cars, and the race, appeared to be spreading joy wherever it went, and not just with the sideline observers.

Making our way from checkpoint to checkpoint, pacing ourselves, stopping for an affogato halfway in Siena - all of it was part of the magic of the 1000 Miglia.

Yes, it is one of the most challenging things I'll ever do, and, though a trophy was not at stake, the win of racing such a gorgeous vehicle in such a spectacular landscape was greater than any trophy could be.

The Mille claims to be "the most beautiful race in the world" and that's valid. It isn't just the cars that make it beautiful, though they have a large part in it. It's the combination of cars, landscape, spectators, and the friends you make along the way, as cliché as that may be.