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Skip the rental-car counter: This clever app will put you behind the wheel of a classic ride on your next vacation.

Most vintage cars spend much of their life sitting in a garage. After experiences with peer-to-peer apps for renting boats or vacation houses, Peter Zawadzki realized that this parked stock represented an untapped resource, not just for financial gain, but also for fun. In order to share the joys of driving a cool old car without the pain points of ownership, Zawadzki and some colleagues designed an app called Classics & Exotics. 

Unlike a South Beach apartment, old cars have a propensity for breaking down, crashing, and stranding. So to make this project viable, Zawadzki required contingencies. He found them in Hagerty, one of the world’s largest insurers of collectible vehicles and provider of no-haggle valuation policies and expert roadside assistance. Hagerty was so intrigued that it bought his company, changed its name to DriveShare, and relaunched it.

DriveShare now has about 600 cars in its system, scattered around the country. “The popular vehicles are classics that are easy to drive and iconic, cars like Ford Mustangs and Porsche 911s,” Zawadzki says. “Cars that put a smile on everyone’s face.” 

It's almost 50 years old, but the 280 SL is as easy to drive as a modern car.

The site also hosts exotics like Ferraris and Lamborghinis, stately cruisers like midcentury Cadillacs and Lincolns, and baroque oddballs like a Zimmer Golden Spirit. Drivers can refine their search by location, vehicle type, brand, and features. They can also sort by price, which is set by the owner and ranges from around $100 to $2,500 per day. Some precious vehicles are available just for static use—fashion shoots, marketing events—which has accounted for about one-quarter of the company’s business. But most are rented for memorable experiences: vacations, birthdays, weddings, reunions.

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We signed up, got vetted by Hagerty’s insurance adjusters, and tested the app during a recent trip to Southern California. We were in Los Angeles and needed something ideal to drive down the coast to San Diego for the day. Something comfortable but elegant and not too finicky, and something in which we could enjoy the view. We choose a pristine 1970 Mercedes 280 SL, a stately two-seat convertible.

Hollywood glam: The author and his rented vintage Benz.

The process was beyond seamless. The owner, Xavier, an avid collector and owner of an immense classic car storage garage, texted us a pickup address and informed us of his rules. And that was that. The immaculate and slaver-worthy facility was just a few miles from our hotel, and when we arrived, a helpful gentleman showed us around the car’s features and quirks and sent us on our way. The sun shone, the push-button radio blared, and the entire 300-mile trip occurred without a hitch. We gassed up the car and returned it and can’t wait to try another DriveShare in Las Vegas, Detroit, or at home in New York.

As owners of four vintage cars, we did wonder why someone would loan out one of their beloved babies to a complete stranger. We posed this question to Xavier after our drive, and he had a few anodyne responses about it being a great way to meet people and make memories. But then he hit on the magic answer. “I like to drive my cars every day,” he said. “But I don’t have enough feet or arms to drive all of them. So I need to share.”

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This makes perfect sense. Old cars that are used often are less likely to break down than those that sit for months at a time. “Cars like to be exercised,” Zawadzki says. “To have their fluids circulated, tires rolling, and gasoline refreshed. It keeps them happy.”

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