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After the gang returns for a new semester, London finds she doesn't have enough closet space, Cody deals with his voice cracking, and Zack's fake welcome buddy plan falls flat when Woody reveals it to his target. The whole gang ends up in London's closet lifeboat and Woody accidentally sets them adrift. After escaping sharks and arguing over supplies, Cody and Bailey argue about which way to set sail, and though the crew sides with Bailey, Cody changes the sail during the night, landing them on a deserted island. Bailey angrily breaks up with Cody. Cody thinks that manly outdoorsman Zack is winning Bailey's heart over the next few days. London, however, thinks that she has won an all-expense paid trip to a five-star island resort, and Woody is stuck with keeping up the facade. Cody desperately tries to win Bailey back, and comes up with a plan to get everyone back to the ship. Meanwhile, Mr. Moseby and Ms. Tutweiller search the ship for the five teens, and end up adrift in their own boat, having the same argument that Cody and Bailey had.
- Matthew Timmons as Woody Fink, Erin Cardillo as Emma Tutweiller, Michelle DeFraites as Jenna
- This is a one-hour episode and was broadcast in 4:3 letterbox on Disney Channel's standard-definition feed (the first episode of a Disney Channel series to be shown in this format on the SD feed). All previous and subsequent episodes are shown in a 4:3 full-screen pan and scan picture format on the SD feed.