Strictly speaking, characters in Pieces of Eight! are privateers rather than pirates. They are captains who have been granted Letters of Marque by the English Admiralty – effectively, a license to prey on the shipping of other nations. Drake and Hawkins were privateers; Blackbeard was a pirate. Practically speaking, the difference is mostly one of social acceptance, and in this game we tend to talk about pirates for the sake of familiarity. But if Blackbeard had been captured by the British he would have been hanged, whereas Drake and Hawkins were knighted for their efforts. Most of the famous pirates we know of date from a later period than that in which Pieces of Eight! is (loosely) set: there are loads of good books out there if you want to find out more about such villains as Bartholomew Roberts and 'Calico Jack' Rackham. A couple of recommended ones are The Crimson Book of Pirates, by Peter Newark, and The Pirate Picture, by Rayner Thrower.
Although we tend to think of pirates as being exclusively male, and of course this was predominantly the case, there were quite a number of female pirates as well, such as the infamous Anne Bonney and Mary Read. There's an excellent book called Bold in Her Breeches, edited by Jo Stanley, which talks entertainingly about the contribution women have made to piracy. In Pieces of Eight! we try to stay gender-neutral.
The game does not deal with the minutiae of tactical-scale movement across the detailed map of the Spanish Main. Instead, each season you must design a strategy your ship and crew are to follow, by combining standing orders together to cover the eventualities it may face. As your crew gain in experience, more orders, or more complicated ones, become available, and the sophistication of your strategy will deepen – hopefully, bringing with it more success, although this will also depend on the strategies adopted by other players. Think of it as a quasi-biological system of competitive evolution of predators – can you find your ecological niche?