Before there was Las Vegas, there was Port Royal: a city of pirates, plunder, and peril clinging to the southern edge of Jamaica. The 17th-century hotspot was once the beating, drunken heart of the Caribbean, until one Sunday in 1692, when the earth opened up and swallowed it whole (quite literally). There’s more truth to Disney’s tales of Captain Jack Sparrow than you might realise.

By the late 1600s, Port Royal was considered to be the crown jewel of the Caribbean – although on second thoughts, “crown” may be a bit too generous a description. In reality, Port Royal was probably more like a golden tooth: gleaming, ostentatious, and clearly quite rotten.

Founded by the Spanish in 1494, Port Royal officially became a British outpost after the Brits wrestled Jamaica from Spanish hands. Its location at the mouth of Kingston Harbour, smack in the middle of Spanish-controlled seas, made it the perfect launchpad for privateers.

Privateers were essentially pirates on the British payroll. They were legally allowed to rob Spanish ships on behalf of the British Crown, which made them both criminals and civil servants, depending on the week’s foreign policy. When England and Spain were at war, the privateers were “heroic seamen”. When peace between the two countries returned, they were downgraded back to pirates, or simply thieves with boats.

Still, privateering was a profitable arrangement. Gold and silver from Spanish galleons poured into Port Royal like rain, and soon the place was booming. In its absolute heyday, it had a population of almost 8,000, and that population sure liked to party. In July 1661 alone, 40 licenses were granted to open new taverns. By 1662, Port Royal was recorded as having one tavern for every ten residents.

Sin City by the sea

If you squinted, Port Royal looked a bit like London, with its narrow cobble streets, brick-and-wood houses, busy merchants, and the occasional pickpocket. But the similarities stopped there.

This was the kind of town where morality was the exception, not the norm. Public drunkenness was normal, gambling was a civic pastime, and prostitution wasn’t just tolerated, it was practically part of the tourism industry. Sailors fresh off the high seas filled the taverns, flinging coins and curses in equal measure. There were carpenters and cobblers, shipwrights and blacksmiths, all feeding off the booming pirate economy. Money sloshed through the streets as freely as the rum, and few cared to question where it all came from.

The key to Port Royal’s popularity was its exceptionally deep harbour, which allowed up to 500 ships to dock at once. This meant constant trade and an equally constant influx of trouble. The city was built, quite literally, on sand – a fragile spit of land that jutted out into the Caribbean. Geographically, it was a risky position, but no one seemed to worry about geology when the economy was this good. As the population grew, more land was laid dry to make space for new buildings. The pirates were essentially stealing territory from the sea itself.

To the devout back in England, Port Royal was less a colony and more a cautionary tale; a sun-drenched Babylon in the tropics. Clergymen called it “the wickedest city on earth.” And like any good biblical story, the ending would be apocalyptic.

June 7, 1692

It was a Sunday morning, just before noon. The markets were busy, the taverns already humming, and the church bells likely ringing with irony. Then the ground began to shake.

At first, people thought it was a passing tremor. But within seconds, the shaking turned violent. Brick walls cracked, the church tower crumbled, and the harbour churned like a pot of boiling stew.

Modern geologists estimate it was a magnitude 7.7 earthquake that struck not just Port Royal, but the whole of Jamaica. That’s an enormous force unleashed directly beneath a city built on sand. And that sand was about to betray them.

When earthquakes hit sandy soil, an eerie process called liquefaction happens. The solid ground suddenly behaves like water, and everything sitting on it begins to sink. The ground that Port Royal was built on didn’t crack or heave during the earthquake – it essentially liquified. Two-thirds of the city slid straight down into the sea. Buildings vanished whole. Streets folded in on themselves. People, animals, and homes were all pulled under in a matter of minutes.

For a city long accused of sin, it was the most literal form of damnation imaginable. But the earthquake was just Act One.

Moments after the ground stopped shaking, the sea struck back. The shifting seabed had triggered a tsunami, or more precisely, what scientists call a “seiche wave”. The harbour turned into a giant sloshing bowl, with water surging back and forth, smashing ships against each other and flinging them inland. One British vessel, the HMS Swan, was hurled across the city and deposited inside a house. This impossible image was confirmed by archaeologists centuries later when they found the ship’s hull still lodged in the building’s ruins.

In the space of minutes, Port Royal was unmade through an almost biblical trifecta of earthquake, liquefaction, and tsunami.

A city cursed twice

The survivors, which numbered around 4,000 immediately after the earthquake, stumbled through a landscape that barely resembled the city they knew. Half of Port Royal was at the bottom of the sea, and what was left on land was reduced to rubble.

Wells were contaminated, food quickly ran out, and disease swept through the survivors. Within weeks, another 2,000 had died from injuries, infection, or thirst. To the British back home, the disaster was divine justice. Pamphlets declared the city’s destruction proof of God’s wrath. It was a convenient narrative – sin, punishment, lesson learned – but it ignored the geological explanation. The city had been built in exactly the wrong place, on a sandbar barely holding itself together. And when nature pushed back, there was nothing man, government or pirate could do to stop it.

When money trumps sense

Today, Port Royal is a treasure trove for archaeologists, a kind of Caribbean Atlantis that tells its story brick by perfectly preserved brick.

Modern dives have mapped entire blocks of the old city, revealing homes, shops, and even the remnants of Fort James. Artifacts like coins, pipes, pottery and even sealed bottles of wine can be found in the remnants of eerie underwater buildings. The city that once epitomised greed and excess now lies in perfect silence, inhabited only by fish. Above it, ships still glide into Kingston Harbour, probably unaware that beneath their hulls lies a city once called “the richest and wickedest on earth.”

If there’s a lesson in Port Royal’s story, it’s not the one preached by the moralists of 1692. It’s simpler and far more human. Every civilisation has its Port Royal moment – that point where success turns into overconfidence and growth outpaces good sense. The pirates in this story just happened to build theirs on sand.

Three hundred years later, as coastal cities expand into floodplains and developers pave over wetlands, Port Royal’s story feels less like ancient history and more like a prophecy. As modern skylines rise higher, it’s worth remembering that nature has never needed a sermon to deliver a reckoning.

About the author: Dominique Olivier

Dominique Olivier is the founder of human.writer, where she uses her love of storytelling and ideation to help brands solve problems.

She is a weekly columnist in Ghost Mail and collaborates with The Finance Ghost on Ghost Mail Weekender, a Sunday publication designed to help you be more interesting. She now also writes a regular column for Daily Maverick.

Dominique can be reached on LinkedIn here.