From 1656 to 1671, Port Royal, Jamaica was the capital of the buccaneers and was known as the Wickedest City on Earth.

Jamaica was an English colony, but it wasn't defended by the British, leaving it vulnerable to attack by the Spanish. However, they had a large population of pirates and buccaneers who were offered letters of marque to defend the island from Spain. The pirates eagerly agreed, establishing their base of operations at Port Royal. Soon, the city was divided into a buccaneer quarter and a smaller genteel quarter. The privateers didn't bother the wealthy plantation owners, except with their noise, and the plantation owners tolerated the buccaneers because of their military value.

The pirates' quarter of Port Royal quickly became notorious for the large amount of sinning going on there. Taverns, brothels, and gambling houses lined almost every block. Sir Henry Morgan often arrived in the city to celebrate the success of his raids -- he would set a huge cask of Spanish wine in the middle of the street and command all who passed to stop and have a drink with him. His victory celebrations often lasted for days.

When Spain and England allied against France in 1671, the letters of marque were revoked, but pirates continued to slip into Port Royal in small groups for entertainment and recruitment, though they no longer had the run of the town.

In 1692, an earthquake destroyed Port Royal, and the Wickedest City on Earth ceased to exist. This was seized on by many preachers as proof of God's vengeance, leading to many anti-piracy sermons.

-brazil- reminds me that Morgan himself was the city's vice governor (Yes, it's a real title, and no, it doesn't mean governor of vice!) during his last years.

Research: GURPS Swashbucklers, Third Edition, by Steffan O'Sullivan, (C) 1999 by Steve Jackson Games, pp. 68-69.