Port Royale 2? Maybe it's not directly about pirates but you can choose to be one. It has trading, ship battles and is located on the Caribbean sea. I remember really liking it .
@ravensword: According to this article - link you should be more than fine. You won't be able to fully use that 5k display, but even monster pc can't do that. Blizzard's games are always made to work on wide variety of specs - starcraft 2 worked on my cheap pc from 2007.
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