After graduating from finishing school as a well-bred Fancy Lad, Nathanial Mayweather (Chris Elliott) prepares for a trip to Hawaii. But his plans are dashed when he mistakenly boards The Filthy Whore, a fishing boat manned by a ragtag crew of salty shipmates, and soon becomes the vessels hapless Cabin Boy. On his journey, he woos the feisty but beautiful Trina (Melora Walters) and encounters a host of eye-rubbing curiosities including an amiable shark man, a savage ice monster, a tobacco-chewing cupcake, and a six-armed seductress (Ann Magnuson) who relieves Nathanial of his virginity, much to the displeasure of her 30-foot salesman husband (Mike Starr).