Cody takes Zack with him to visit his guru, a Swami who lives in the top of a mountain who charges high prices for everything he sells. Mr. Moseby is having computer problems and is trying to contact the call center for help, but without any success. Padma, who was originally London's roommate on the ship, but left after London bribed her, asks London to help convince her mother that she was still at sea.
The ship docks near Rome and London falls for a young, handsome musician named Luca while playing in the streets. Later, as Bailey searches for her money belt key, she overhears that Luca and his uncle, Marco, are actually con men and had already conned London for twenty thousand dollars.
London holds a competition between Cody and Woody to decide which one of them will accompany her on her trip to the Tipton Space Station. Desperate to win, Cody and Woody each try to sabotage the other during the competition. Meanwhile, Zack is in charge of the senior citizen's activities and meets a passenger who is unwilling to participate in any of the activities.
When Bailey starts feeling homesick, Cody decides to recreate her hometown festival. However, thanks to London, Bailey's hometown boyfriend, Moose, shows up. He and Cody compete in corn bobbin', arm wrestling, and chess to win Bailey's heart, but Cody loses every competition.
Hannah Montana boards the S.S. Tipton on her way to a concert performance in Honolulu. To impress Bailey, Cody enlists Woody to help him get tickets. Meanwhile, the Russos use a little magic to spice up their vacation. Alex pulls a prank on Justin for which Mr. Moseby blames Zack, while Max introduces London to a magical suitcase.
When their cooking teacher accidentally gets injured, Cody fills in and becomes the rock star chef that all the girls fawn over. When Bailey tries to get Codys attention, he ignores her to hide his true feelings for her. Meanwhile, London tries to pass off Zacks artwork as her own
Zack pulls a prank on Woody but instead of Woody falling for it it was Becky the captain of the wrestling team. In order for Zack not to get beaten up he tells Becky that he likes her and wants to go out with her. Meanwhile, Cody and Bailey try to help London study for the finals.
Zack turns in one of Cody's old term papers as his own, without realizing Cody applied to a bizarre passage about a fictional banana phobia, so Mrs. Tutweiller sends him to see a counselor, ending with Zack taking his anger out on his brother. Meanwhile, London goes through withdrawal when her cell phone is taken away after she is caught texting during class, prompting Bailey to find a new thing that she can do to keep her hands busy.