Old Port Royal, Pirate City

Just south of Cuba on the southern coast of Jamaica, Port Royal was founded by the British, who after gaining control of the island from the Spanish in 1655, began fortifying the settlement next to the deep harbor which eventually would hold as many as 500 ships.
Out of fear of Spanish invasion, buccaneers were drawn away from nearby Tortuga to help discourage attack, and after peace with Spain in 1660, those same buccaneers easily acquired letters of marque to plunder their merchant ships.
Read more at The Pirate's Realm.