Buccaneer was the first pirate board game I played, at the tender age of around 10 or 11. One of the first games that I worked out how to play on my own by fiddling with the rules- Pirate Cap'n Steve was soon raiding convoys of spanish ships- aarrgghhh!
My all time favourite boardgame was one that came with a VHS tape which the players interacted with- Skull and Crossbones. Pretty old now, but copies come up on ebay occasionally. Boardgamegeek has a review and some snaps of the playing pieces (boardgamegeek review of skull and crossbones). Lots of laughs when played with a group.
Couple of other sources for cheap pirate playing pieces.
Pirates Edge of Ocean is great for providing cheap card ships, in our house they go up against GW Men of War and Dreadfleet ships.
The kids were into Playmobile pirates as kids, and were great for rpg or gaming. The older cannons fired toy cannonballs so a simple line up and knock em down shooting match was fun. In fact I better go and dig them out this weekend, just to make sure that they are all still in decent shape... and that the cannons still work. Arrrgggghhh!
