I spent so many hours playing pirates! on my c64. It was absolutely amazing .

same here, on my amiga 500 and later on the PC. i was a kid and barely able to understand what was going on (but that didn't matter that much anyway), my english was absolutely inadequate for the text. i remember pestering my father about the vocabulary: "what does 'squashbuckler' mean? what's 'swashbuckler'? what's 'merchantman' and 'the flying dutchman'?" (the last was actually a misreading of "she's flying dutch colors" when you looked at a dutch ship). the worst was when i got too far north-west and had to sail back into settled territory against the wind, which took ages. something else that stuck in my mind was the soundtrack - iirc mostly händel and bach.

ps: years later i found the "mount & blade" series (which i too love), which is roughly the same but medieval and on land.