Bailey is an attractive girl from Kettlecorn, Kansas. Although she loves her life in Kettlecorn, she wishes to explore the world around her and masquerades as a boy in order to attend Seven Seas High on the cruise liner, SS Tipton. Since Bailey doubles as a boy's name and because she has played for a boys' baseball team, she manages to become a student at Seven Seas High.

After fooling the crew into believing that she is a male, she becomes Zack's cabin-mate. At first, the two clash because Zack is messy while Bailey is more hygienic and feminine. However, after her real gender is found out by Zack, he promises to keep it a secret.

Cody quickly becomes suspicious of the two; and it's not long before Bailey's real gender is revealed to the entire crew. However, since London Tipton had a cabin to herself (after bribing her old cabin-mate to leave), Bailey was still able to stay and be cabin-mates with her. Bailey was excited at the thought of sharing with London but the Tipton heiress opposed it. Annoyed at the whole idea of staying on the SS Tipton, London flees to Parrot Island, leaving Bailey feeling responsible and guilty over her disappearance.

When everyone goes to retrieve London from the island, Bailey tags along and helps them not only escape the island, but also rescue London. Along the way, she even manages to get a pet pig named Porkers. By the time they return to the ship, London reluctantly decides to be a little more friendly to Bailey. They even started to bond, as Bailey helps London pick out fancy clothes. However, despite their friendship, London often embarrasses Bailey, especially by picking on her. In the episode "The Kidney of the Sea", she and London have an intelligence test with Porkers and London's dog, Ivana, and it is revealed that Bailey was once a cheerleader at her high school back in Kettlecorn when Porkers wins and Bailey does a victory cheer for him. In the episode "Boo You", London embarrasses Bailey by telling her internet show viewers that Bailey's underwear resembles a parachute. In the same episode, London informs her viewers that Bailey snores. When the students return after a school break in "Lost at Sea", London briefly forgets Bailey's name. In the episode "Mulch Ado About Nothing" Bailey appears to have feelings for Cody at the end of the episode. In "When in Rome", she says that a "big city" is "any place where the mayor is not a goose". In "Showgirls", Bailey receives the first detention of her school career. In "In the Line of Duty", Zack (serving as Hall Monitor) gives Bailey detention on consecutive days, once for breaking curfew with Cody and once for running in the halls with London.

In "Beauty and the Fleeced" Bailey is shown to be a good singer when she wins the originally fake pageant started by Zack, Woody, and Marcus. In almost every episode, Bailey is shown wearing skinny jeans and plaid or checker board. In" Can You Dig It?" Princess Xaria's spirit possesses Bailey. When Cody finds out, he has to get the crown and put it on her statue. Bailey is eventually saved and Princess Xaria's spirit (a sparkly green mist) goes back in her statue. But London stupidly takes the crown because she has short-term memory, and is possessed by Princess Xaria.

Zack states in "Rat Tale" that Bailey has an overbite, to which Cody defensively replies by saying that this is because she had to use braces made from chicken wire when her family couldn't afford real ones.

In the third season, Bailey temporarily went to Kettlecorn to help her family because a tractor fell on her uncle. She returned to the SS Tiptonin the episode "Bon Voyage".

In the episode "The Play's The Thing", Cody writes a play in which he shows that Bailey was the main reason of their break-up, as a result Bailey runs off crying, thus making Cody feel remorseful, he goes to make-up and get back with Bailey, but she is so upset that she slams the door in his face. She and Cody get back together in Twister: Part 2.

In the episode "Graduation on Deck", Bailey is accepted to Yale, which Cody is not. She chooses Cody over Yale, but later decides to still go, because Cody tells her that she can't miss the opportunity, and that he will come visit her.