At a carnival, Corky (Chris Burke
) enters a church raffle for an all-expenses-paid trip to Hawaii. At the restaurant, Becca (Kellie Martin
) has to turn down plans with Tyler because of work, sadly reminiscing about their perfect kiss at the Spring Fling. Drew (Bill Smitrovich
) and Libby (Patti LuPone
) meet with Corky's various teachers, who say that despite his sincere efforts, he is not doing well in his mainstream classes. They suggest that he take on an entirely special-ed curriculum or get tutoring, which frustrates Corky. Just when the family wonders if they are plagued with bad luck, Father McMichaels arrives at the house and tells them that Corky won the Hawaii trip. Corky excitedly declares his intentions to learn how to surf, and when Becca tells him that their parents never had time for a proper vacation after their wedding, he decides that the trip will count as their official honeymoon. Becca debates staying behind, as do Drew and Libby, worried about leaving the restaurant for so long, but Drew decides that they deserve the break and puts his brother Richard in charge, much to Libby's concern and chef Hans' fury.
When they arrive in Hawaii, they quickly discover that some of their luggage is missing, as is the promised "official greeter" and limo service. Finally, they are met by a man named Earl (Denis Arndt
) who provides them with lackluster leis and takes them in his broken-down van to the hotel, which turns out to be a dirty shack infested with geckos. The family is highly disappointed, and Corky clearly feels guilty. Their attempts to book a flight back home fail, but Libby assures Corky that it is not his fault, and they decide to "make it an adventure" and go to see singer Don Ho
in person. When they arrive at the concert venue, however, they learn that the travel company gave them expired tickets. Corky and Becca sadly tell a man in the crowd about their series of mishaps and their desire to give their parents a good honeymoon, and he helps to get them into the concert. Don Ho takes the stage, and the kids are stunned to realize that he is the man who helped them. Don invites Drew onstage to sing "Tiny Bubbles" with him, and also arranges for the Thachers to move to a swanky hotel. Drew calls Richard and is relieved to hear that he has patched things up with Hans, so to speak. Earl arrives at the hotel and the family is not pleased to see him, but he begs them for a second chance and ends up taking them on a grand tour of Oahu, during which Corky finally gets a chance to go surfing. [See if you can spot the locations from "Lost
"!] The Thachers go out for a fancy dinner, and Don Ho arrives again to treat them to the meal. Libby then joins him in singing a Hawaiian wedding song in honor of their honeymoon, and Corky is thrilled that things turned out so well.