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Sid Meier's Pirates! - Game cheats, tips and tricks for XBox
Easy sea battles:
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While battling other ships, get in front of them. Get them to chase you,
and when your guns are fully loaded, turn, fire, and straighten again.
Repeat this until you want to board or their sail falls and they surrender.
This is best done when you use grape shot or chain shot.
Easy Specialists:
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Attack and board a smuggler's vessel to usually get a specialist
(for example, Carpenter, Sailmaker, etc.).