You play as Skipper, and Gilligan has to lead Skipper to certain areas. In each level, the millionaire and his wife, The Movie Star, 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 can now be played online here.
This game contains examples of:
- Be Careful What You Wish For: At the end of the game, the castaways end up at the Ice Cream Mountain. It's a disappointment. And leaves out a message that reads Will the castaways ever get out of this deserted island? Stay tuned!.
- Bears Are Bad News: The game has four area bosses, and one of them is simply an angry bear.
- Dem Bones: A skeleton is another one of the game's bosses.
- 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.
- 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.
- Timed Mission: When Gilligan is lost somewhere, your timer will lower to two minutes. The timer is restored upon Gilligan being found.