Ferrari 250 GTO

Ferrari made just 39 of these elegant race cars between 1962 and 1964, so they are extremely rare. “The 250 GTO is probably the holy grail in terms of value and recognition, but the reality is only a handful of people in the world will ever have the chance to legitimately drive one,” Hagerty says. An early model fetched $38 million at Bonhams’ Quail Lodge auction at the Pebble Beach Concours d’Elegance two years ago. If that’s too pricey, know that any 1960s Prancing Horse with a V12 engine is worthy of making the list.
Aston Martin DB4

The precursor to James Bond’s getaway car, the Aston Martin DB4 is an iconic workhorse. “The DB4 is a thoroughbred that never gets flustered,” Hagerty says. “I wouldn’t hesitate to drive one across the country. It’s no wonder that James Bond favored the derivative DB5.” They’re in short supply, so if you want to drive one, your best bet may be to befriend a collector.
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BMW 3.0 CSL
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If any part of you harbors a race-track fantasy, this is the car to track down. When BMW came to America in 1975, it brought a quartet of models with it, including the 3.0 CSL coupe. Driven by racing legends Brian Redman, Sam Posey, and Hans Stuck, the car claimed victory at the 12 Hours of Sebring race that year and won Daytona the following year. The pair of triumphs established BMW’s performance chops stateside. In addition to its engineering and performance legacy, the 3.0 CSL pioneered a host of technologies found in later BMW models, from its first-ever four-valve six-cylinder engine to its early anti-lock braking system. BMW offers a turn at the wheel as part of its BMW Classic Center in Munich.
Acura NSX

Acura’s halo car from 1990 to 2005, the NSX is young but mighty. “While it’s not as sexy as its European rivals, the Acura NSX showed the rest of the world that supercar specs and daily-driver manners could co-exist,” Hagerty says. “It inspires confidence and begs you to keep pushing, braking later, and turning harder. It may be the most underrated car on this list.” Its successor, the new Acura NSX, reaches customers this year and is likely to inspire renewed interest in the original. Fortunately, Acura made 9,000 first-generation NSX cars so finding one online is easy.
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Shelby GT350

Also known as the Cobra, this high-performance descendant of the Ford Mustang was a darling of the late 1960s. With Ford’s V8 engine, the Shelby GT350 was a legitimate racecar for the street. “When you get into it and turn the key, the car doesn’t only rumble audibly, it also actually shimmies side-to-side and up-and-down, just a bit,” Hagerty says. “And that’s while it’s still parked. When you get on the gas it leaps and roars.” You will quickly see why designer Carroll Shelby is lauded as a 20th-century motoring genius. To drive a vintage Cobra, visit a high-end classic car auction house, dealer, or specialized broker.
Ford Model T

Produced from 1908 to 1927, this is the car that birthed the American automotive industry. Affordable by mass market standards, the Model T begat car culture and road trips. “Everyone needs to know where they came from,” Hagerty says. “When it comes to American motoring, that starting place is the Model T.” With a volatile hand-crank engine and two-speed transmission (not including the reverse gear), the Model T isn’t easy to drive, even if you can get your hands on one. But rest assured–27 mph will never feel so thrilling.