If you ever get the chance to buy this game at a reasonable price, for instance in the recent humble bundle sale or gamefly.co.uk sale, DO IT! This game is my childhood so perhaps I'm biased, but for the 2,50€ I paid for this game it's a steal.
Although relatively short, you'll finish it in around 15 hours if you don't waste too much time, Sid Meier's Pirates! includes a variety of era's to play (1600-20, 20-40, ... , 80-1700) each with a different twist to it.
As you progress your difficulty will be ramped up slightly if you want to, however for people who want a real challenge I dare you to try out swashbuckler without losing a ship.
-Variety of Ships to take
-Ability to conquer cities and create your own 'world'
-Repetitive mechanics (Dancing, Fencing, Naval warfare)
-No 'endless' mode available