Jamaica
How else could the honorable Henry Morgan celebrate his 30 years of governing Jamaica than with a race around the island? Gathering every Pirate and Buccaneer around, the "Great Challenge" will be a memorable race. Not to mention - what's better than a race where you can earn some booty and shoot at your opponents? The ''Great Challenge'', that's what. The goal is to sail around the island of Jamaica as fast as possible, while gathering the goods required: gold for port taxes, powder for naval battles and food to eat while out on the high seas. Each time the pirates meet, they will have to fight to try and steal the contents of each other's holds (and maybe pawn off a chest full of cursed gold at the same time). And so, hoist up the sails and head towards Port-Royal. May the fastest and richest win.