Sid Meier's Pirates!
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Easter Eggs brought to you by 
Brother Jeff
Randomly and rarely, the monk that greets you at a Jesuit monestary will be replaced with a likeness of Jeff Briggs, the CEO of Firaxis Games. He lacks the distinct shaved skullcap and pudgy cheeks of the normal monk, and instead sports a goatee and a completely shaved head. He otherwise acts like a normal Jesuit monk.
Mysterious Sid
In rare and random occasions, the Mysterious Traveler at the back of the tavern will instead be Sid Meier, the executive producer of the game. He will be most distinct, as he lacks the trademark beard of the other mysterious travelers. He otherwise acts just like a normal Mysterious Traveler.
No easter eggs here, matey
Open up the Piratopedia and look up the entry for St. Eustatius. Early in the entry the word 'Eastern' is used and only the 'Easter' part of it is a hyperlink. Click it to access a hidden page that firmly denies the existence of any easter eggs in Sid Meier's Pirates.
Talk Like a Pirate Day in Sid Meier's Pirates!
When the data of the computer is set to September 19th (International Talk Like a Pirate Day), everyone will talk differently in the game. You will become ye. Avast, Shiver me timbers, and Arr will punctuate every other sentence. Nothing like a beautiful daughter of a governer talkin in pirate!
The dialogue is noticably different from the standard fare. Even in the menus and the narrator.