Howard Hughes, Hugh Hefner, Hurley Haywood. There must be something about those initials that breeds a certain type of character into a man. One who ventures off the beaten path, and, in Hurley Haywood's case, speeds past behind the wheel of your favorite Porsche.

In 1977, Hurley captured his first major win at the the 24 Hours of Le Mans, the longest-running sports car endurance race in the world. Since then, Haywood has won more endurance classics than any other racer in history. He's also a member of the Motorsports Hall of Fame of America and has popped in-and-out of retirement more times than Jay-Z and Brett Favre. In fact, the active vice president of Brumos Porsche in Jacksonville, Fla., just drove for Porsche in the 2011 Rolex Series GT.

We recently spoke with Hurley about his favorite places to drive, as well as the sketchiest spots requiring extreme caution. We figured the living legend knows a thing or two about where to cruise. Join us as we travel the globe in style, a.k.a. inside Hurley's souped-up Porsche, holding on for dear life.

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