Without a cabin boy, Greybar forces Nathaniel to do the chores in return for taking him to Hawaii, as well as teaching him how to become a better, more mature, person. The ship is caught in a fierce storm and Kenny is knocked overboard and drowns.
However, the crew reaches Hell's Bucket, a Bermuda Triangle-like area where weird events occur. Nathaniel unsuccessfully tries to convince each fisherman to set sail to Hawaii, but convinces Kenny into doing so. It is not until the next morning that Captain Greybar (Ritch Brinkley) finds Nathaniel in his room and explains that the boat will not return to dry land for three months. He thinks the ship, The Filthy Whore, is a theme boat. Nathaniel makes a wrong turn into a small fishing village where he meets the imbecilic cabin boy/first mate Kenny ( Andy Richter). After annoying the limo driver who is taking him to board the boat, he is forced to walk the rest of the way. After graduation, he is invited by his father to sail to Hawaii aboard the Queen Catherine.
Nathaniel Mayweather ( Chris Elliott) is a snobbish, self-centered, arrogant, despicable, loathsome virginal man.
