Skully's friend, Winger, has a problem. She gets a letter, saying that there is treasure for her on Skybird Island, but she couldn't find Skybird Island anywhere, but Jake and the crew agree to help find the island and the treasure. The crew thinks that Skybird Island would be in the sky, so they all fly to the island, using Izzy's Pixie Dust. Captain Hook sees them flying around, and wonders what they are up to. He pulls out his "Whirly-Hook" and Mr. Smee grabs onto his legs and they take off into the air. Soon, Jake and the crew find the island, and find directions to the treasure. Once they get to a statue, which they think is the treasure, Winger flies up and knocks on a small door. A Wise Old Parrot walks out, and says that Princess Winger has returned, and Winger finally realizes that she is the Princess of Skybird Island. They put a crown on her head and start singing happily, but, just then, Hook grabs the crown off her head, and starts running away with it. Fortunately, Skully flies up and grabs it out of his hand, putting it back on Winger's head. She thanks them for helping her, then the crew returns back to Pirate Island.
- Jake and his crew collect ten gold doubloons.
- Kevin D. Campbell was the writer for this episode.
- The episode marks the first appearance of Winger and Wise Old Parrot.
- Colin Ford as Jake
- Madison Pettis as Izzy
- Jonathan Morgan Heit as Cubby
- David Arquette as Skully
- Corey Burton as Captain Hook
- Jeff Bennett as Mr. Smee
- Loren Hoskins as Sharky
- Jeff Bennett (speaking)/Kevin Hendrickson (singing) as Bones
- Lisa Loeb as Winger
- Adam West as Wise Old Parrot