The film sets in 1910's, Pippi Longstocking (Shannon Elizabeth) a young orphan flees into a small city where he moves in. Soon after moving in, she befriends her playmates, Tommy and Annika, (David Tentrant and Pamelyn Ferdin) and the three soon became fast friends. While playing, they met Goofy (Bill Farmer) and Donald (Tony Anselmo). Later, Pippi throws pancakes at them and gives them a wild chase. After they run away, Mr. Nilsson (Frank Welker) Pippi's monkey, is worried sick from vomit soon a rabbit named Bigwig (Michael Graham Cox) has given a flower has Mr. Nilsson has feeling better. As the first day at school, Pippi, Tommy and Annika ride her horse and it's running faster by her friends Ord, (Ty Olsson) Mickey, (Wayne Allwine) And Bigwig's younger brother Fiver (Richard Briers) the horse smushes the school door by a teacher (Elizabeth Montgomery). Pippi used to tell stories about he goes into a short island and fights snakes. After he finishes the story, Ord talks to the teacher while Zephir keeps Agnes Fluffy (Heather O'Rourke) out of the door. Another day, Tommy and Annika came to Villa Villekula cottage and Pippi tells the others why did her parents are killed by a weasel, Except Tommy and Annika who they have a mother without a father, so they invited by Cassie, (Chantal Strand) Until Zak and Wheezie (Jason Michas and Kathleen Barr) had fund the circus. While at the circus, Pippi decided to go on the stage and finds a orphaned lemur named Mort (Robby Benson) belonging to King Julien (Danny Jacobs), who adopts them and annoys Julien. By the day he was scrubbing the floors and haves an wild chase from cutting tomatoes on the streets. The next day, Tommy and Annika are in a punishment with an naughty boy who is kept beating up by the other kids, Zephir (Jeff Pustil) has been messing up the boarding school because the cat will get him. Then, the three brought Bigwig to the office, who is badly beaten and shot. Back at Villa Villekula, the policemen Kling and Klang (Jan Sigurd and Tomas Blome) tell them that the people had an coffee party. The worried kids are disappointed at this and runs away. While on an journey, they find an garden that they have flowers on it. Then, there's something on the bushes. It was Bigwig, who was hiding through somewhere in the woods. After the horse loves pancakes, Tommy finds a ball and Annika saws it, a ship had appeared. The ship was floating away and Pippi accidentally loses Tommy, Annika and Bigwig and takes them while Bigwig jumps in the water and swims faster Pippi tells him that he was an good swimmer and Bigwig thanked him. They explore the ship and crashes straight. Pippi tells Bigwig that he'll take care of her horse and the bunny leaves. Ord was in the poop deck because he was so afraid of heights when Bigwig shows up. Then Zak was so dreadful when Bigwig had fixed the ship. It was sunset and Agnes discuss with Mickey, The cute toddler Boo (Emily Deschanel), Zephir and Mort. Then suddenly, the ship has going to sank and ran toward Goofy and Donald again. Before the ship was sinking, Bigwig promises Pippi that he can put right to the surface. Meanwhile, Goofy and Donald have an plan to arrest Pippi, Bigwig and Fiver, but tackles Goofy and the three escape. Outside in the boat, Bigwig tells Pippi that he loves him and jumps by an boat. Tommy and Annika hop on a boat while Bigwig is trying to snap the rope. When Ord is saved by the younger kids while they row away, the boat lands in the water and Bigwig fell overboard. After the ship sank, they're rescued by an another ship, Bigwig is realizing that Pippi wouldn't let go. So Pippi and the gang decided to go back where they belong and the journey continues.