The plot revolves around Larry's attempt at winning a weekly contest held on the ship by Captain Thygh, a gorgeous blonde. The contest involves a series of other games varying from legitimate sports competitions like bowling to naughtier things like a machine created to test one's sexual prowess. Each passenger is given a score card with a selection of the various competitions to compete in, and the passenger with the highest cumulative score at the end of the week wins. The prize is an additional free week on the cruise spent sharing the Captain's cabin (and, presumably, her bed.) The player must come up with a variety of ways to cheat in each of Larry's assigned competitions so that he can get the highest score and win the contest. Among Larry's chosen competitions are a cooking contest, a "best dressed" contest, a game of horseshoes, bowling, the sexual prowess contest and others. At times Larry wins these contests not by cheating but only by an unexpected twist of fate triggered by his (often unintentional) actions. For instance, Larry's encounter with fashion designer Jamie Lee Coitus causes his Leisure Suit to become the height of fashion; as such he wins the best dressed competition. Similar to Leisure Suit Larry 5: Passionate Patti Does a Little Undercover Work, it is impossible for the game to be placed in an "unwinnable" state, by a bad decision.