Snob Diaries: Mapping the Mille Miglia with Sam Tracy
Snob Diaries is a personal recap of seasonal fashion and cultural events around the world, told through the lens of our staff and close friends. For Mille Miglia, Highsnob's own Sam Tracy takes us on a joy ride through Brescia with Maserati.
Oh, Italy. Land of indulgent lunches, unhurried conversations, and style that looks easy but is anything but accidental. Nestled in the Mediterranean and swaddled in centuries of obsession with beauty—be it architectural, culinary, or sartorial—Italy’s long been the blueprint for living well. Their way of life, dubbed la dolce vita, has long been studied as the golden ratio of lifestyle design: good weather, great food, and even better fashion. From perfectly tailored trousers to the monumental sweep of an ancient archway and the operatic roar of a hand-tuned engine echoing through a stone alleyway, Italy is where form and function fall madly in love.
Perhaps there’s no better place to experience it firsthand than along the historic route of the annual Mille Miglia: 1,000 miles of rolling landscapes, roaring engines, and high-octane glam.
A vintage car rally first raced in 1927, the Mille Miglia is part gearhead pilgrimage, part open-air museum that zips through the country’s cobblestoned past and present. From Brescia to Rome and back, antique automobile collectors race their prized possessions along winding countryside roads and medieval piazzas. So when I’m invited to experience the first half of this year’s race behind the wheel of the Maserati Grecale—the brand’s sleekest SUV to date—I can’t help but say sì. From Brescia to Bologna, onward to Siena, and finally into Rome, this is the Maserati Grand Tour. No checkpoints to hit, no trophies to chase—just curated playlists, long lunches, and one very well-dressed machine.
The kickoff point is Brescia, a Lombardian city where Roman columns share real estate with racing stripes. Beyond the weaving narrow streets and the midmorning clatter of espresso cups in Piazza della Loggia, antique engines begin to warm up like opera tenors stretching before curtain call. Slipping past a row of shuttered gelaterias and selfie-snapping tourists, I stumble upon the red carpet of car culture. Sunvisored superfans line the barricades, clutching posters and adjusting their wristwatches as gleaming vintage cars roar into the lineup like runway models in chrome.
A red Maserati A6GCS/53, one of this year’s glitzy competitors, peels away from the starting line. Flashbulbs pop.
Parked slightly apart, the Maserati Grecale takes in the scene like a fashion editor in the front row. This time, not dressed in archival nostalgia, but in crisp, modern precision. Like a good outfit formula, the elements are equally intentional: hand-stitched leather with a buttery finish, customizable trim with just the right amount of sheen, and seats contoured like they’re tailored to your frame. You don’t just sit in it—you’re dressed by it. And fine Italian tailoring is definitely something I can stand (and sit) by.
Onward to Bologna: the city of porticoes and Parmigiano. We roll into town just in time to witness Virtus Segafredo basketball fans spill into the streets after a nail-biter playoff win, flags waving, chants echoing under the arcades. The Maserati Grecale navigates the commotion with a confident low purr. Fitting, really. Maserati got its start here in 1914, and more than a century later, Bologna still knows how to build a legend.
The next morning, the journey south unravels into, well, my (and probably yours, too!) Pinterest dream. Cypress trees punctuate rolling hills, and silvery olive groves glimmer under the famed Tuscan sun. The Grecale’s drive mode dial, trimmed in knurled aluminum, glints in the morning light like a piece of fine jewelry—and my favorite accessory of the day. With the windows down and a playlist oscillating between Mina and Anna Pepe (in fitting past-and-present proportions), I catch the scent of sun-warmed wildflowers and distant woodsmoke.
We pull into Siena right at lunchtime as the Mille Miglia pauses for its most sacred pit stop of the day: a proper meal. The walled city’s renowned Piazza del Campo hums with idling motors as rows upon rows of gleaming vintage cars form with geometric precision. More continue to roll in. With machines of this pedigree, this isn’t so much a parking lot but an open-air gallery in motion. Drivers and their map-clutching, time-checking co-drivers wander off in linen shirts and driving gloves, disappearing into side streets in search of pasta and a quick caffè. Engines cool, wine glasses clink, and pigeons weave through the crowd like they, too, have reservations. Only in Italy could a high-stakes race make room for a leisurely lunch.
As the sun begins to shift and set the terracotta facades glowing, it’s our cue to head south—Rome is calling.
Finally, the Eternal City. A mosaic of ancient history, modern drama, and timeless glamor. Gazing out the windshield, I catch a glimpse of Rome’s theater of style: a perfectly knotted scarf here, a purposeful cigarette flick there, and of course, a leather-wrapped steering wheel under my freshly polished grip. Hey Siri, como si dice “chic”? The Maserati Grecale glides through Trevi’s cobblestone maze with ease, its adaptive air suspension smoothing out centuries-old streets like they were freshly paved. By the time we make our final turn, the city has draped itself in golden hour and goodbyes.
As I hand over the keys, I can’t help but say it: ciao, bella. With the Maserati Grand Tour coming to an end and the first half of the Mille Miglia now in our rearview, surrendering the Maserati Grecale feels like returning a borrowed couture coat: necessary, but heartbreakingly hard.
As they say, some trips are measured in miles, others in moments…but why choose one when you can have both, stitched together like a piece of fine Italian tailoring? From espresso in Brescia to aperitivo in Rome, the Maserati Grecale was not just transportation, but an essential part of the outfit (and arguably, the most eyecatching). Because for me, the Mille Miglia isn’t about getting there the fastest, but about how you arrive. Preferably in something as well-made as your favorite leather jacket—and with just enough aura to stop traffic.
