Located below the eastern end of Cuba, in the heart of the Spanish Main, Jamaica was the perfect base for pirates intent on plundering Spain's New World treasure ships as they sailed the high seas bound for Cadiz. Many of these bloodthirsty nomads operated out of the city of Port Royal.

Overview
Set between the Blue Mountains and a sunlit turquoise sea, Port Royal appeared blessed, but in what seemed the act of a vengeful God, most of this "wickedest city in Christendom" was destroyed in a 1692 earthquake, leaving two-thirds of the city beneath the sea. "Jamaica was once all about the pirates," says Rodney Campbell, a denizen of the Port Royal pier. "Look closely and you'll see reminders of them everywhere."

Port Royal is the starting point for this journey into history. What remains of Port Royal lies at the tip of a 9-mile (14-kilometer) breakwater road called the Palisadoes, which partially encircles Kingston harbor, with Norman Manley airport halfway down its length. Here you can pick up a rental car to set off on your 380-mile (612-kilometer) trip. Beginning in Port Royal, this excursion first goes east, past a beached freighter, into Kingston. From there, a roughly clockwise circumnavigation of the island will take you past green savannas, sugarcane fields, and mountains, with the azure Caribbean in the distance.

Start in Port Royal
On approach to Port Royal, a faded Red Stripe sign proclaims the old city, "Where the Buccaneers Drank their Beer." This once swashbuckling enclave is now a quiet fishing town—one in which Red Stripe flows at the tumbledown Fisherman's Cabin on a harborside pier. Captain Henry Morgan, the city's foremost citizen, triumphantly returned to Port Royal in 1668 after famously looting the "impregnable" Spanish stronghold of Portobelo, Panama. Port Royal retains such buccaneer sites as St. Peter's Church. Inside is the silver communion service said to have been donated by Captain Morgan. Beyond St. Peter's, Fort Charles appears largely as it did at the time of the 1692 earthquake. Its Maritime Museum is rich in pipes, tools, dishes, and other archaeological artifacts rescued from the sunken part of the city. Across a green that was once a British army parade ground, original battlements overlook the site of the sunken pirate vessel Ranger. Down a side street is the Old Gaol, which withstood the earthquake and is now a pharmacy with a sign for Ting soda on its ancient facade.