When it comes to actual "items" I would choose the Necklace of the Navigator. Also, I'd like Lemonhead's sculpture: the Wimpy Little Idol, to put on my desk.
If we are including people, well I would love to join the Brimstone Beach Club and have a good laugh with Wally, while we watch Guybrush terrorize the cabana boy. That's the perfect vacation right there.
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