Located on an eight-square-mile coral island off the southern tip of Florida, Key West is the southernmost city in the continental United States. Its location and environment give the place a mystique as the Last Resort, the place where mainland North America dribbles to an ambiguous end in the Caribbean. As an artifact of popular culture, Key West generates powerful and often contradictory cultural messages: it is at once a quintessential Navy town and a haven for literary figures, beachcombers, and assorted eccentrics. During the Cuban Missile Crisis in 1962 and thereafter, it served the rhetoric of American presidents as a rugged outpost of democracy vis-á-vis Castro's Cuba with its Russian missiles "just 90 miles from our shores."

Contrary to popular belief, the name Key West has nothing to do with the island's western aspect in the Florida Keys, which seem to drift languorously from the...