Port Royal, Jamaica

In the Pirates of the Caribbean, Port Royal is where Captain Jack Sparrow is jailed before being freed by Will Turner. In reality, 16th-century buccaneers (pirates originally from Hispaniola) were encouraged by the British government to settle in this major shipping center and attack passing French and Spanish vessels. It endured as a hedonistic pirate enclave—the “Wickedest City on Earth”—until June 1692, when a massive earthquake sent a huge chunk of the town to the ocean floor, killing thousands. “Some considered the quake divine retribution for its sins,” says Marc Nucup of The Mariners’ Museum in Virginia.

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