Sorry to break this to you, but your assumptions are incorrect. Jack sparrow was not based on calico jack at all. He was written as the staggering, flailing character you see, and the writers had bugs bunny in mind as far as how he goes about doing things. Johnny depp added to that by playing him as a strange combination of keith richards (who appears in 3 and 4 as captain teague, jack's father) and pepe le pew. The only real connections to 'calico' jack rackham are his first name and his flag.
And i'd hardly say that elizabeth swann was based on the ladies you mentioned, any more than geena davis's character in cutthroat island was. The only similarities are their sex and the pirate thing.
The only place where they dipped into real history was using blackbeard in the fourth film, and even that was mentioned as being posthumous to his encounter at ocracoke island with robert maynard.
And while they never state exactly when the movies take place, port royal was destroyed by an earthquake in 1692, while edward teach/thatch was killed in 1718, which means almt three decades would have passed between the first film and the fourth. Or maybe it's just disney, playing it fast and loose with history for the sake of entertainment...
"Cinema was made for fantasy, rather than normal types of stories." - Ray Harryhausen
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