HMF said:
There is a "Very Rough" timeline which suggests the ride pre-dates the films both literally and figuratively.
The ride and films clearly don't take place in the same world. All the more reason to get rid of the ill-fitting movie updates.
At the risk of sounding a little "spergy," when the first film came out, one could have argued that it possibly takes place in the same world as the ride because the various homages were NOT spot-on recreations. What I mean by that is there were no attempts made to recreate specific settings/characters/etc from the ride, just the general idea of "pirate ship vs. fort," "jailed pirates trying to get key from dog," "pirate sleeping in mud with pigs," etc., so there was nothing that contradicted the idea of the events, locations, and characters of the ride and the events, locations, and characters of
Curse of the Black Pearl co-existing in the same fictional universe at different points in history. The town from the ride is not Port Royal or Tortuga, the ride's caves are not the caves of Isla de Muerta, etc.
But as the series went on this became harder to reconcile. The latest film included a ship called "Wicked Wench" in the flashback sequence, which is the name of the ship from the ride and the original name of the Black Pearl in the lore of the films, and they didn't even bother to make it resemble the ship from the ride (not even in color scheme). Even if they had, the Black Pearl is structurally different from the ride's ship so it wouldn't have made sense anyway. The new movie makes Barbossa's presence on the ride's Wicked Wench make even less sense than it already did.
And from a stylistic standpoint, notice NONE of the pirates in the movies wear striped shirts or striped socks or hats with little skull-and-crossbones symbols embroidered on them. The aesthetic of the movie pirates is influenced more by the art of Howard Pyle than Marc Davis.
Plus, "the ride" exists in many different forms, so if one were to say "the ride" and movies take place in the same universe, which version of "the ride" are we talking about? The original WDW POTC has many variations from the DL version, as does the Paris version, and so on.
TL;DR - the film series is only loosely based on the ride(s), it's not the same universe at all, and it's pointless to try to figure out where on the "timeline" the ride fits with the movies, because it's obvious neither the filmmakers nor the Imagineers in charge of the updates were thinking about any of this.
