"The game doesn't have a default windowed mode so you have to edit the config file to make this possible. You can find this config file by going to your home directory and navigating to Library/Preferences/Firaxis Games/Sid Meier's Pirates/My Games/Game. Open the "Config.ini" file with TextEdit and add the line "fullscreen = 0" to the bottom of the list. Then save the change you just made to this file, quit text edit, and you're ready to go. Obviously you'll want to make sure the game's resolution is set lower than that of your monitor's resolution or else the window won't fit." source
this is a site for Mac gaming by the looks of it, but i see no reason why it wouldn't work on a pc. it can be a good idea to back up config files before you edit them.
If that doesn't work, google for DXWnd, I just tested it for COD2 and it works (nothing else I tried would work), so it may allow you to run other stubborn games in a windowed mode...
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