Stupidity: When Governor Swann is trying to encourage his daughter while she's locked within the ship's chambers trying to escape, she climbs down to a boat. Nobody in the Navy would have left a boat there, neither would Jack (and why would he, especially without anyone noticing?). The boat just mysteriously appears to help her escape.
Continuity mistake: Either the first shot has a gratuitous view of the fort or the composite people neglected to add the fort in the second shot. Norrington says, "...this is the day that Capt. Jack Sparrow almost escaped. Take him away." The night shot that follows, shows the bridge archway, and beyond it the pier, Interceptor, the fort and its parapet. After Will breaks Jack out of prison, they approach the same archway and beyond it is the pier and Interceptor, but in this shot we don't see the fort and its parapet, nor the line that Jack slid down the day before. The camera angle is exactly the same. (00:27:15 - 00:44:30)
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