Female Jack Sparrows... hmmm. I always had a soft spot for Joanna from Jeffrey Farnol's 'Martin Conisby' stories. Admittedly at the end she 'dies for lurve', stepping into the path of a bullet meant for the hero, but up until then she is awesome and quite Sigrunny. Not bad for a character from a story written early last century and set in the 1600s. And she is a playful gadfly to the dreadfully grim and solemn hero. At one point she non-fatally poisons him for fun, because she thinks a spot of puking will unbend him a bit. And she makes one helluva pirate queen.
Then, in a completely different context, there's Cordelia Naismith from the Miles Vorkosigan stories by Lois McMaster Bujold. Less goofy but equally badass, and a female character with depth and with her own moral compass, completely different to that of the mostly male characters around her. That series is full of strong and well developed female characters, actually. Well worth a read. And explores some interesting questions. Like, at one point, Ekaterin (Cordelia's eventual daughter-in-law) is debating with herself about the life of her aunt, who is a history professor, wife, mother and remarkable person, in terms of that whole career/life balance thing, and how women often sacrifice one aspect of life to get the others - it's quite philosophical.
Those stories also explore gender issues in some very interesting ways. One of the major characters is a hermaphrodite, from a race experimentally made that way. And there's a whole novel, 'Ethan of Athos', peripheral to the main story, set around a character from a world where the entire population is male. And a whole lot of exploration of what being freed from the necessity for direct biological reproduction does to the human psyche, sexuality, gender concepts and culture. All in some rattling good yarns. Read them in order, the story is better so.
