Wickedest City On Earth- Port Royal Jamaica. Once the richest and wickedest city in the world, Port Royal was the pirate capital of the Caribbean. Home to legends like Sir Henry Morgan, Port Royal overflowed with taverns, brothels , churches and over 6000 souls. A virtual Las Vegas of the 17th century. On June 7th 1692, a massive earthquake shook the island and within minutes, the city sank beneath the waves. Over 4000 died and Port Royal became a ghost town beneath the sea. Cheers to Pirate Tal