Epic Europe: Cruising from Milan to Florence in a 1969 Alfa Romeo

It is April in Milan, and the city is in full bloom, its palazzi and sunbaked sidewalks flooded with well-dressed designers and other creative types attending the annual Salone del Mobile furniture fair. Not far from the bustling fairgrounds, however, at the Four Seasons Hotel Milan, the topic of conversation isn’t Tom Dixon or Ron Arad; it is instead Alfa Romeo, Porsche, and Mercedes-Benz.

“Are you comfortable driving a stick?” asks Martino Motta Pirman, the CEO of the vintage-car agency Joey Rent. Pirman’s company has partnered with the Four Seasons to offer a new road-trip experience, and he is sizing me up as a driver.

I answer with a resounding yes—my daily driver is a 6-speed—and eagerly ask which vintage model Pirman has picked out for me. “Aspetta, ragazza!” he responds. Wait.

To be sure, any car enthusiast would share in my excitement. Introduced in April, the Route to La Dolce Vita is an exquisite auto lover’s adventure in which travelers take one of Joey Rent’s classic cars on a curated road trip between the Four Seasons Hotel Milan, the Four Seasons Hotel Florence, and the Grand Hôtel du Cap-Ferrat, a Four Seasons Hotel, on the French Riviera. Along the way, they can explore the Mediterranean towns of Portofino and the Cinque Terre, the Barolo wine country, the Carrara marble mines, the famed Mille Miglia rally route, and much more. Throughout the trip, a guide from Joey Rent follows the travelers in a modern car—connected via radio for seamless communication—​ensuring VIP service at every turn.

Guests have five cars to choose from, ranging from a 1956 Porsche 356 A Speedster (the car that James Dean made famous) to a 1958 Mercedes-Benz 190 SL Roadster. On this fine spring morning, however, I have asked Pirman to surprise me with a car of his choice—and the anticipation is killing me. Fortunately, I am awaiting my fate in the Four Seasons’ pale-pink Renaissance Suite (a favorite of Karl Lagerfeld), fantasizing about winding country roads and ochre landscapes while dining on a decadent breakfast of eggs Benedict and flaky croissants.

At last my chariot arrives, a pristine fire-engine-red gem. “Questa macchina è bellissima, sì?”—This car is beautiful, right?—asks my Joey Rent guide, Manuel. It’s a soft-top 1969 Alfa Romeo Spider: a quintessential Italian 4-speed roadster designed by Pininfarina, and one of the best-kept secrets on the vintage market. Its simple lines, rounded wings, recessed lights, and elongated wheelbase all add to its movie-star good looks.

With Manuel at my side in the passenger’s seat (a request I’ve made because of my status as a solo traveler), I maneuver the Spider through narrow lanes and traffic-filled boulevards until the lively city streets turn into rolling green countryside. The crisp smell of the car’s beautifully worn dark-blue-leather interior fills my nostrils; the husky purr of its 1.3-liter twin-cam engine courses through my body. Nearing Parma, we pass acre after acre of farmland dotted with grazing cows—the magicians behind the region’s Parmigiano-​Reggiano cheese. An hour later, we whiz past the canary-yellow Ferrari Museum of Modena.

We eventually stop just outside of Bologna’s city center for a mouthwatering lunch of Parmesan, prosciutto, and traditional Bolognese tortellini in brodo at La Bottega di Franco. Stomach full, I am back behind the wheel just as a cluster of ominous-looking clouds disperses to reveal a brilliant blue sky. The sun reflects brightly off my windshield as I navigate southward past quiet hamlets and ancient villages where modest stone churches and centuries-​old castles dot the verdant views. Eventually the landscape changes once again, this time ceding to the familiar red rooftops of Florence.

It’s a bittersweet moment when Manuel and I roll up to the Four Seasons Hotel Florence. The restored palazzo’s Renaissance-era portico is a welcome sight, but I have become quite attached to my Spider after a long and blissful drive. My separation anxiety eases, however, as I step inside and glimpse the hotel’s frescoed lobby and statue-filled garden—just another stop on the route to la dolce vita.