Came across a game called 'Pirate Simulator'
That's the working title at least, it's still in development. Screenies here
http://www.galaxyproductions.net/piratesimulator/
There is some discussion on a couple of 'pirate game' forums about it and the developer is saying that the focus is on realism, features etc. Gameplay is the most important part, but the graphics obviously aren't going to hurt the eye
They're not under deadlines from publishers either and that they will only release when the game is finished.
They've just signed up for the beta, originally they wanted the release for summer '07, looks like they'll have beta testing during march or april so maybe mid year? The game will be downloadable so no worrying about distribution I guess.