Simple Strategic Fun
This is a very fun game. There have been many iterations of this game, I have no idea if this is the best but it is very good. As the title suggests you play as a swashbuckling young Pirate out to make a fortune of gold-bullion, battle ships, have sword-fights with mortal enemies and retire a rich, happy and wealthy man. As with all of Sid Meier's games there is a ridiculous amount of replayability. Firstly there are 5 difficulty settings. Then there are five eras though only the easiest era is available on the easiest difficulty setting. You can play any of the other eras on any of the other difficulties. And then there are 4 countries, one of which you start the game allied to. So overall there are almost a hundred combinations in which to start the game. Also you can retire your man whenever you want which I think is a very nice touch if you feel you have been playing that game for too long. Then just create a new character and off you go again.
If you have liked any of Sid Meier's previous games you will probably like this. Any interest in pirates obviously helps. However I'd recommend everyone give it a shot. Some of the minigames may seem a little outdated in terms of control though one is extremely like a very popular tactical GBA game called Advance Wars... not as complex or as deep mind you, after all it's a minigame but still there are a large number of similarities. Overall the game is easy to get into and play and I've had a really good time playing it.