This is a proven true story: During a recent media group tour of Rome, highlighting the city’s lifestyle attractions for men, a young journalist from Brooklyn noticed that the cars filling the Eternal City’s hyperactive streets lacked the kind of buzz he often saw in New York (ie, sporty stripes, spinning wheels, and tinted windows). He then shrugged, saying, “Italy shouldn’t have much of a car culture.” Notably, no one spoke to that guy for the rest of the trip. You just can’t be wrong about something so obvious and survive the moment.
No nation has the same kind of open emotional love affair with the automobile, and the innate sense of competition that proper driving provides, as Italy. Yes, the machine built the USA and forged its self-image. And the Germans pour their meticulousness into their automotive engineering. The Japanese rebuilt their post-war economy with cars. But Italy will always see four wheels and an engine with the eyes of love and artistic expression.
Consider the spiaggine, Italy’s iconic open-air beach cars that became symbols of the Dolce Vita line of jets and the ultimate summer accessory along the Amalfi Coast. The annual Mille Miglia is known as “the most beautiful race in the world”, in which hundreds of vintage automobiles travel a 1,800 kilometer loop from Brescia to Rome and back. Italian sports cars are tailored like the best suits, and Emilia-Romagna’s Motor Valley is home to world-renowned brands such as Ferrari, Lamborghiniand Maserati.
As a result, most of the most desired and expensive cars at auction or among private collectors are Italian, led, surprisingly, by the creations of Enzo Ferrari and his team. The racing powerhouse built consumer cars primarily to fund the boss’s track ambitions, and a mix of those competitive speed machines and the road cars they inspired dominate the auction podiums.
Ferrari specializes in amassing enough editions of its rare breeds to drive bidding hawks crazy. Consider the 1962-1964 Ferrari 250 GTO. The Enzo made just 36 of the dominant racers in those three years, making the 250 GTO perhaps the most prized auction target. in 2014, Bonhams brought the hammer to a 250 for $38,115,000, while Sotheby’s sold another in 2023 for $51,705,000.
From Modena, Ferrari consistently places more entries on the most valuable auction lists than any other company, because its creations of the 50s and 60s are wonderful and extremely rare. Only four 1955 Ferrari 410 Sport Spiders ever left the factory, and RM Sotheby’s consigned it to a private buyer in 2022 for $22,005,000. There are four examples of the 1956 Ferrari 290 MM, so RM Sotheby’s has it back in 2018 for $22,005,000. Finally, two of the 1961 Ferrari 250 GT SWB California Spider Competizione legends hit the world and Christie’s delivered one to a new home for $25,305,000 in 2025.
Moving forward from the 1960s, it’s constantly difficult to say exactly which additional Ferraris rise above their supercar relatives. It’s the 1987 F40, with its mid-engine, rear-wheel drive. Its successor the F50 in 1995 improved on the formula with a 4.7 liter V12 powerplant. However, the Ferrari 458 appeared in 2009 to overtake both. Pumping out up to 597 horsepower, there’s something about the cut of the Italian tailoring that identifies it as the stereotypical modern Ferrari.
While the brand may not own Ferrari trophies or awards, Alfa Romeo is the most charming car manufacturer in Italy. With their unmistakable tri-oval fender grilles and total dedication to driving fun, there are few lines of old-money cars with such enduring style. The crazy lines of the 1952 Alfa Romeo Disco Volante and 1967 33 Stradale perfectly thumb their noses at the rest of the car world as “we really love or hate cars” candidates. The light and sporty Giulia Sprint GTA of 1965 improved on its hardline boxer relatives of the time to become an all-time favourite.
But the perfect Alfa Romeo is the Spider. The roadster convertible defined its genre in various guises from 1966 to 1994. Swapping the full grille for a shield badge and presenting an ergonomic challenge to some of the world’s tallest drivers, there really isn’t a more classic Italian car than Alfa Romeo’s arachnid.
Standing among the smaller classic cars, Fiat The 500 rivals the UK’s Mini as the coolest pocket car ever. Built off-and-on from 1957 to 1975 (and reborn through an American partnership in 2007), the three-door hatchback could fit in any city in the world, but it seems most appropriate in Venice or Florence.
Finally, Italy leads the world in the supercar class, home of machines that demand attention and are never shy about their capabilities and MSRPs. While Lamborghini continues to make waves this century with the Gallardo, Aventador, Huracán and Revuelto, the Lambo that graced the walls of the youngest teenagers in history has to be the Countach. In production from 1974 to 1990, its low, angular lines carried design appeal from the 70s to the 80s. They didn’t come to a supermodel standard, but they could have, and no one would bat an eye.
A lesser-known but defiantly edged hypercar completes the Italian supercar. The Pagani Zonda lived in different guises from 1999 to 2019, but each had a slick spoiler, solid wheel wells and up to a 7.3 liter V12 engine. In keeping with its Roman predecessors, a Zonda wanted to be the bravest of the brave, letting smaller cars know they were looking at another Caesar.
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