Might I recommend Sid Meier's Pirates! This is one of those games that you can just pick up and start playing at any time. You get to plunder and/or sink ships; shoot cannons from one ship to another; sword-duel with ship captains, fort guards, bar drunks, and jealous fiancees; find buried treasure; romance governors' daughters; partake in ground battles (tactical style); sack cities and change their nationalities; go on escort missions that affect the political environment of the game; deliver treaties and/or war-instigating letters; fight anyone from the Spanish, English, Dutch, French, Pirates, and/or Native Americans; save kidnapped family members...the things you can do in this game are endless. And the beauty of it is you can save the game and leave at any time, and come right back to where you were whenever you want.
Shoot...just thinking about this game makes me want to play it right now (I have the XBOX version).
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