Oh, the glory days of the Macintosh in middle school.

All I remember about this game is it was something to do with pirates. The game started out with a neat form of copy protection, where you had some sort of battle with the captain (?) and if you didn't do it right (as directed by having the physical game documentation, I suppose), you started out the game pretty crippled as a sort of punishment.

I want to say there were ship-to-ship battles on the sea, but that memory is not so clear, and it could be too much honey mustard on my sausages.

Ring a bell for anyone? Definitely existed prior to 1994, but I can't be more specific than that.