There is a nice Pirate / Privateer Expansion in "East India Company" if you like the little slugish combat it might be fun and I do fancy the looks.

[url=http://en.wikipedia.org/wiki/Corsairs:_Conquest_at_Sea]Corsairs: Conquest at Sea[/url]
Pirates of the Caribbean

Enjoyed both of them quite a lot.

Game Dev Tycoon??

Aye! Second that! Plus "Ghost Pirates of Vooju Island.
Yer list ain´t full weethou´ Monkey Island, ye know.

I think we know which of us circles "International Talk Like A Pirate Day" every year on his calendar. :P

Nice suggestions here, some I already have (and some even finished, like Jolly Rover) and some I never heard about! Thanks to the great community, and keep on posting! :-)

Corsairs: Conquest at Sea Technically you are not playing as a filthy pirate but civilized and sophisticated privateer but it doesn't change your agenda too much ;)

Sea Legends

Captain Morgane and the Golden Turtle
Dead Reefs

Both adventure games - neither are on gog, but you can find them at gamersgate. I have both, but I haven't played either yet, so can't give any opinions.

Apparently there was a DOS version of Hook

http://www.mobygames.com/game/dos/hook_

You caould always try Pirate 101 jk ;-)

Carribbean is a pirate RPG from the makers of Mount & Blade’s expansion

Coming out in September