If you agree to the barmaid's suggestion to visit the upstairs room with her in the tavern at the pirate fort on Hispaniola, she doesn't appear in the room with you to do the normal exit dialogue, and disappears from the game afterwards (until you die and get revived there, that brings her back).
I think perhaps she doesn't spawn correctly in that tiny room.
I think perhaps she doesn't spawn correctly in that tiny room.