You play as Skipper, and have to lead Gilligan to certain areas. In each level, the Howells, the Professor, and Mary Ann each give out clues and missions, including a blue club for boss fights. There are also items such as bananas to restore the player's energy, rope to teleport Gilligan back to Skipper, and hourglasses to increase the time.
This game contains examples of:
- Adapted Out: Ginger is completely absent, most likely due to Tina Louise not wanting to give the game the rights to her likeness.
- All for Nothing: Episode 3 ends with The stone tablets being revealed to be pieces of a drawing that Gilligan made.
- Episode 4 ends with Gilligan accidentally wasting the wishing idol to create a giant mountain of ice cream.
- Bears Are Bad News: The main boss of episode 3 is an angry bear.
- Damsel in Distress: Episode 2 is about Mary Ann getting kidnapped by headhunters, and the main goal of the episode is to rescue her.
- Later, in episode 4, Mrs. Howell gets kidnapped under the same circumstances, though rescuing her is not the main objective of the chapter.
- Dem Bones: A skeleton is the final boss of the game.
- Escort Game: You play as the Skipper with Gilligan following you everywhere, contributing nothing but asinine comments like "Isn't this beautiful scenery, Skipper!" You can't be apart for more than 2 minutes, and he needs to be with you whenever you talk to an NPC to get the next Fetch Quest. To make things worse, he has a tendency to get stuck on obstacles and fall into pits leading to previous areas.
- Fetch Quest: The entire game is based around talking to the next NPC or finding the next item, occasionally having to fight a boss for it. At one point, Mary Ann asks you to tell Mr. Howell that "dinner won't be for a while", then Mr. Howell says he needs a piece of Mary Ann's pie, and after another round trip to actually get and deliver the pie, Mr. Howell finally tells you that Mary Ann had the "secret weapon" you were looking for the entire time.
- Good Old Fisticuffs: Playing as Skipper, a punch is the default way of dealing with your enemies.
- Killer Gorilla: The main boss of Episode 1 is a gorilla that stole the Professor's transmitter.
- The Load: True to the show, Gilligan is one. You'll frequently need to rescue him from the deep holes he keeps managing to fall into.
- Primitive Clubs: Skipper can get one in each chapter. It's required to beat each of the bosses.
- Quest for a Wish: The final chapter of the game involves the castaways trying to find an idol that will grant them one wish, which they can hopefully use to get off the island.
- Quicksand Sucks: A recurring obstacle. The player has to mash the jump button in order to move through it.
- Timed Mission: Every stage in the game is one. When Gilligan is lost somewhere, your timer will lower to two minutes. The timer is restored upon Gilligan being found.
- Wasteful Wishing: The ending of the final stage. The castaways finally get their hands on the idol, only for Gilligan to rhetorically say that he wishes he had a mountain of ice cream.