At the onset of "Random Tropical Paradise", Harry Fluder's life was working out exactly as planned: great job, loyal friends, and the perfect fiancee - until he caught his perfect fiancee having sex with one of his maybe not-so-loyal friends at their wedding.

With the wedding cancelled and honeymoon already paid for, Bowie, Harry's best man, convinces Harry to take him along on a "homie-moon." What is supposed to be a refreshing weekend of rest and relaxation turns into an all-out bonkers adventure of epic proportions of sex, drugs, overall mayhem, and mafia intrigue.