A Lamborghini Murcielago to Lake Como
Though he's a Porsche loyalist, Dempsey understands the lure of piloting the right vehicle in the right country. Take, for instance, the time he was tossed the keys to a Versace Edition Lamborghini Murcielago while doing a Versace shoot in Italy.
"I got to drive it from Como all the way down to Milan, and had a blast because I had a police escort and hauled ass the whole way."
Not that he needed special permission to enjoy the fashion-tinged screamer. "It was great to open it up," Dempsey says. "You have these great brands that are quintessential to their country. You go with Porsche in Germany and Lamborghini in Italy."