He aqui una cosilla que he encontrado en 4chan, sobre diferentes momentos en el juego en que se apunta que todo transcurre en realidad en un mundo dentro de una atracción de feria que puede que sea mística y que tenga cierta realidad paralela donde ellos son mayores, o que en realidad todo esté sucediendo en la mente de guybrush niño, imaginandose a si mismo como un pirata de verdad. Muy interesante la parte de las camisetas: Por qué nunca son de nuestra talla? quizás porque guybrush es en realidad un niño y le vienen grandes? El comentario de Ron Gilbert acerca de inspirarse en lo que pasaria si pudiera deambular a sus anchas por la atraccion de Pirates of the Caribbean (creo que la atraccion real es un tren que te lleva por dentro de un tunel y tal) me parece tambien muy relevante.
El comentario aqui:
>MI1
There are already several hints that the world is really a theme park. The prizes you win for different challenges are all t-shirts. "not my size, but a nice one nonetheless" has a theme park prize vibe to it. There's a vending machine at Stan's. If you ask one of the swordfighting pirates "why are you talking like that?" they respond "play along Guybrush, it's how they talked back then."
>MI2
The very start of the game depicts the metal pipes you would expect in a manufactured theme park terrain. The treehouse on Phatt Island looks just like the Swiss Family Treehouse from Disneyland. Big Whoop being an E-ticket (E-ticket being the best ticket at Disneyland) and the icon for it even looks like the magic castle. Guybrush can travel between islands, for free, with no time at all having passed, because this isn't real ship travel - it's just different parts of the theme park.
>Pirates of the Caribbean Ride
Gilbert has cited this as an inspiration, and lots of imagery from the ride is in the games (pic related). He even said "I always wondered about stepping off the ride and exploring." You can imagine Guybrush's initial appearance in MI1, stepping into the screen and saying "I want to be a pirate" as him having just done this. No backstory is given as he is just a kid who has stepped into this piratey world and decided he wants to be a pirate.
>Explanation
Exactly as it appears. Guybrush went exploring. Chuckie decided to chase. A girl got involved (he struggles to talk to her because he's a kid getting nervous when he has a crush). Parents eventually find them at the end.