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.
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.
Heading back to the Jamaica of dancehall music and Bob Marley T-shirts, a drive east along the Palisadoes leads into Kingston, Jamaica's capital city, founded when refugees fled Port Royal after the earthquake. Bob Marley's former home on Hope Road has been turned into a museum featuring his music. From Kingston, journey west along highway A1 for about 18 miles (30 kilometers) to the former Jamaican capital of Spanish Town, where the town's main square is suitably Georgian and includes the remains of the 19th-century Old Courthouse on Constitution Street. On the square's west side, in a former couthouse that was demolished in the 1760s, John "Calico Jack" Rackham, a dandified pirate chief, and his female crew—Anne Bonny and Mary Read—were tried. Following their 1720 capture in Jamaican waters, the three were convicted of piracy—a crime for which Calico Jack was strung up on Rackham's Cay east of Port Royal while the women were sent to the Spanish Town jail, the ruins of which stand behind the Old Courthouse.
From Bluefields, head northwest on the coastal A2 to the resort town of Negril. There, the villas at Rondel Village (www.rondelvillage.com), with their breezy, octagonal architecture, make for a serene and friendly resort set right on Bloody Bay. It was here that John Rackham and his female cohorts were captured. The bay's sandy beach stretches for miles backed by a series of luxury all-inclusive resorts.
Beyond Negril, the coastal highway (now designated the A1) heads north and then eastward, providing commanding vistas of the sea for many of the 40 miles (64 kilometers) to Hopewell, an untidy suburb of Montego Bay. As you approach Hopewell, you'll notice Round Hill, a forested promontory that juts into the western end of Montego Bay's harbor. The five-star Round Hill resort (www.roundhilljamaica.com), built on and named for this feature, is among the most elegant places to stay on the island. At the top of Round Hill, the remains of Round Hill Fort, which protected the harbor from pirates during the early 18th century, offers visitors great views of Montego Bay and the city.
From Montego Bay, it's a 63-mile (101-kilometer) drive along the stunning North Coast to Ocho Rios, where the Henry Morgan portraits begin to reappear. Just outside Port Maria (20 miles/32 kilometers east of Ocho Rios) stands British playwright Noel Coward's Firefly—the estate where he spent the last 20 years of his life. It was from a nearby point that Morgan directed attacks upon passing ships. Coward's composing room—the "Room with a View"—looks out over a gun-slit "pirate cabin" that sheltered Morgan behind thick walls and offers views of Port Maria's harbor and the lighthouse. A hole in the earth that lead to a tunnel that supposedly gave Morgan passage to the sea can be found not far from Coward's hillside gravesite.
End Back in Kingston
Though the buccaneer-related sights thin out as you continue east to Port Antonio, the drive here is one of the most scenic in Jamaica, skirting the Blue Mountains as you round the eastern end of the island and head back west toward Kingston. Just past Port Antonio, stop for some authentic jerk pork at Boston Bay, a laid-back seaside village. As you enjoy your meal and a cold Red Stripe, look out to sea. Who knows, you just might spot a pirate ship along the horizon.
Enjoy this drive any time of year. To contact the Jamaica Tourist Board in the United States, call 800 233 4582.
—Text by Alan Wellikoff, adapted from National Geographic Traveler