Among the last of the Avalon Hill board games I got back when was Richard Berg's Blackbeard (1991). In those days of 2nd Edition AD&D, it had sort of an "old-school D&D" vibe for me.
The players moved their pirate ships around the board, engaging in a variety of buccaneering activities, trying to retire their captains before they got killed (which reduced victory points). The "character" element, and the aspect of choosing which strategies to pursue in a rich game environment, made it feel more like D&D than like an abstract game with a pirate "theme." The "story emerging from play" quality was there!
Berg thoroughly redesigned the game for the 2008 GMT Games version. The hex-grid is gone, and it looks as though it's now probably less suited to solitaire play but better with multiple players. It may also be easier to learn (a good thing if one wishes to get other folks to play). Some elements (e.g., hostages and the Royal Navy) appear to have been expanded. From what I've seen of the components, they retain utility while adding a lot of period/subject color.
I no longer have the old version, but the new one may be at my FLGS (which could order it, I'm sure). It looks as if the first print run sold out and there's now a second edition.
Any players of either version (or better yet both) here?