Jake Truman is just a regular guy. However, at his Grandfathers funeral he is mysteriously handed an envelope. Inside the envelope is a map of an island with the word ‘Monkeyshine’ written across it. Jake has serious thoughts about finding the island, but is soon made to look a fool when his colleagues at the office get wind of his exploration and brand him as a plastic pirate. After a little detective work, he finds out that ‘Monkeyshine’ means ‘Practical Joke’ and assumes that the whole thing is a cruel jibe. That is, until the girl at his office sees the map from a different angle and notices that it doesn’t say ‘Monkeyshine’ at all, but is the name of a place somewhere altogether different, which leads Jake to find out where the map really leads. Jake must look into his soul and follow his heart to find out who he really is, and what he really wants, before he can go to the place his grandfather wanted him to go, and ultimately become the very thing his family have carried on for generations - he must become a modern day pirate in a modern day world.