London, Zack, Cody and Mr. Moseby set sail on the S.S. Tipton for their semester at sea. London convinces her roomate to leave the ship so she can have a room to herself. Cody finds himself sharing a room with Woody, who is very messy, and Zack shares a room with Bailey, who is a neat freak. Nobody knows that Bailey is a girl who disguised herself as a boy in order to gain a position on the ship after she found that there were no more vacancies for girls. Zack and Cody agree to switch roommates, but Zack changes his mind after he finds out that Bailey is a girl. After everyone else eventually finds this out Bailey is allowed to stay, filling the position vacated by London's ex-roommate, and Bailey becomes London's new roommate. This is the last straw for London and she escapes to Parrot Island via helicopter.

Cody arrives in Kettlecorn and is surprised to see that Moose is also there to get Bailey back. A tornado approaches and everyone evacuates into the Pickett's storm shelter. As the tornado hits, Bailey is knocked out and dreams that she is Dorothy Gale and is trying to find her way back home through the Land of Oz. As Bailey unwittingly re-enacts the story of The Wonderful Wizard of Oz, she encounters Moose as the Scarecrow, Cody as the Tin Woodman, Woody as the Cowardly Lion, Zack as a Flying Monkey, London as Glinda the Good Witch and the Wicked Witch of the West, and Mr. Moseby as a Munchkin. She wakes up from her dream and has to decide between Moose and Cody.

The group starts rebuilding Kettlecorn after the tornado, but they continue to struggle to pay off the damage. As a result, London's father, Mr. Tipton arrives (who finally reveals himself) to discuss aiding their monetary costs. Meanwhile, Zack, Woody, and Mr. Moseby attempt to sneak into Kettlecorn with a Search and Rescue team.