Sid Meier's Pirates! has some sort of similarity to what you described
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There was an 80s version of Sid Meier's Pirates also, not sure which one he was referring to. (I never played the original one :/ )
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Hi, so I had this flash a few days ago of this game I played when I was young. Actually I played only a demo of it.
It was a pirate adventure game, but not in the Monkey Island fashion, instead I remember a first-person thing, like Myst, and art style was creepy. Not sure of wich year it was, but probably I was still using Windows 98 (or 95 even); I remember really few details, in the demo you were in a prison, and had to use a mug on the iron bars to make someone appear (maybe a girl?), and I can remember removing brick stones from a wall using a spoon or something like that...
Also, you could die in that game, and there were swordfights involved somehow.
Rings any bell to you?
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