Port Royal, Jamaica

Port Royal: The Wickedest City on Earth

Sailing into the clear blue waters of Kingston Harbour, Port Royal comes quickly into view. Today, it’s hard to imagine that this quiet Caribbean village was once considered one of the largest and most infamous cities in the New World.

In the late seventeenth century, Port Royal’s narrow alleyways and taverns echoed with the riotous behaviour of ruthless pirates and notorious privateers. At its height, it earned the ominous title of “the wickedest city on earth”.

The Origins of Port Royal, Jamaica

When English warships seized Jamaica from the Spanish in 1655, a fort was hastily constructed at Point Cagway. Renamed Port Royal in 1660 to honour the restoration of King Charles II, the settlement was strategically important, but dangerously under-defended.

With too few troops to repel Spanish counterattacks, the English adopted a controversial strategy: they invited hardened pirates and privateers to use the port freely in return for protecting it. The vast natural harbour offered safe anchorage for dozens of galleons, and before long, illicit gold and silver flooded in. Within three decades, Port Royal had grown into a sprawling, wealthy city.

Smuggling, Excess and Lawlessness

By 1690, Port Royal was a powerful trading hub openly dealing in smuggled goods, including enslaved people, raw sugar cane and timber. Merchants with a taste for danger amassed enormous fortunes, but often didn’t live long enough to enjoy them.

The local drink, Kill-Devil Rum, was so strong it reportedly caused hundreds of deaths. Lawlessness was unchecked. The Portuguese pirate Roche Brasiliano became infamous for his extreme cruelty, torturing victims publicly in the streets to instil fear.

Sir Henry Morgan: Pirate, Knight and Governor

In contrast to many of his peers, Captain Henry Morgan cultivated a reputation as a gentleman, at least by pirate standards. A highly successful privateer authorised by England to attack Spanish interests, Morgan coordinated devastating raids across the Caribbean.

His success earned him a knighthood, and he later became Lieutenant Governor of Jamaica. When he died in 1688, aged around fifty-three, he was enormously wealthy and received a lavish state funeral in Port Royal. Some of his silverware can still be seen at St Peter’s Church and the museum at Fort Charles.

However, Morgan was not destined to rest in peace.

The 1692 Earthquake and the Sunken City

In 1692, a catastrophic earthquake, estimated at magnitude 7.5, struck Port Royal. Built on unstable, sandy foundations, large sections of the city liquefied and slid into the sea, taking streets, buildings and Captain Morgan’s grave with them.

Today, submerged pillars, archways and roads remain visible beneath the harbour’s waters, earning Port Royal recognition as a UNESCO World Heritage site.

Nearby Rackham’s Cay marks the location where the body of pirate John “Calico Jack” Rackham was displayed in chains after his execution in 1720, a warning to others. His capture also sealed the fate of his legendary female companions, Mary Read and Anne Bonny, whose ultimate destinies remain shrouded in myth and legend.

Repeated earthquakes, fires and hurricanes prevented Port Royal from ever reclaiming its former glory. By 1770, its days of notoriety were firmly over.

Map of Port Royal by John Taylor, 1688
Image of the sunken city courtesy of GoUNESCO

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