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, the “wickedest city in Christendom”. 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. Jamaica was once all about the pirates.
Set between the Blue Mountains and a sunlit turquoise sea, most of Port Royal was destroyed in a 1692 earthquake, leaving two-thirds of the city beneath the sea. 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. This once swashbuckling enclave is now a quiet fishing town. Port Royal retains such buccaneer sites as St. Peter’s Church. Beyond St. Peter’s, Fort Charles appears largely as it did at the time of the 1692 earthquake. Its Maritime Museum is rich in archaeological artifacts rescued from the sunken part of the city. Original battlements overlook the site of the sunken pirate vessel Ranger. Down a side street is the Old Gaol.
Port Royal is the starting point for this journey into history. Here you can pick up a rental car to set off on your 380-mile (612-kilometer) trip. The excursion is a roughly clockwise circumnavigation of the island past green savannas, sugarcane fields, and mountains, with the azure Caribbean in the distance.
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 30 kilometers to the former Jamaican capital of Spanish Town. In 1720, John “Calico Jack” Rackham, a dandified pirate chief, and his female crew – Anne Bonny and Mary Read – were convicted of piracy—a crime for which Calico Jack was hung while the women were sent to the Spanish Town jail.
From Bluefields, head northwest on the coastal A2 to the resort town of Negril with a sandy beach stretching for miles backed by a series of luxury all-inclusive resorts.
Beyond Negril, the coastal highway (now designated the A1) provides commanding vistas of the sea for many of the 64 kilometers to Hopewell, an untidy suburb of Montego Bay. As you approach Hopewell, Round Hill is a forested promontory that juts into the western end of Montego Bay’s harbor. 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 101-kilometer drive along the stunning North Coast to Ocho Rios. Just outside Port Maria, 32 kilometers east of Ocho Rios is 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. A tunnel not far from Coward’s hillside gravesite gave Morgan passage to the sea.
The drive east to Port Antonio 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.

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I would like to think of myself as a full time traveler. I have been retired since 2006 and in that time have traveled every winter for four to seven months. The months that I am "home", are often also spent on the road, hiking or kayaking. I hope to present a website that describes my travel along with my hiking and sea kayaking experiences.
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