Feeling ignored, Dewey runs away from home and finds a new family: a band of singing and dancing pirates looking to rob Scrooge blind.
The McDucks are on a flight home from their latest destination, with some hiccups among the group: Launchpad is flying unnavigated at the chagrin of Huey Duck, and Dewey is annoyed with the lack of attention and intrigue from his family. All of a sudden, the Sun Chaser is bombarded with hooks of an enemy fleet. The attacker is none other than the dreaded Air Pirates, led by the charismatic and devious Don Karnage.
After the Sky Pirates' musical plunder, Launchpad crashes the plane into a jungle. Scrooge, wanting to get his treasure back, has Huey and Launchpad begin repairing the plane, failing to notice Dewey walk off to find his hat the pirates stole. Dewey soon runs into a pirate and hitches a ride to follow the pirates back to their fleet, just in time for Don Karnage to greet his crew. Despite their successful raid, Karnage chastises his crew for faults in the dance performance, throwing one overboard for turning up late, before his eye turns to Dewey, whom he has tied up for trespassing. While Karnage leaves to plan out Dewey's execution, two of the pirates, Peg Leg Meg and Ugly Mug, listen in to Dewey's tall tales.
Back at the Sun Chaser, Louie finds an enchanted sapphire left behind that beckons him to keep it for himself. Once made aware that Scrooge was looking for the sapphire, Louie comes up with a complex plan to bring it to Scrooge so he can keep it for himself.
Meanwhile, Dewey has amazed the entire Sky Pirate crew with his stories, although their reactions to Dewey's adventurous life leave them feeling useless and underappreciated because of Don Karnage keeping them in the background and constantly berating them. Dewey convinces the crew to start a mutiny and they force Karnage off the plane, giving his captain's hat to Dewey as their new captain. On ground, Karnage vows revenge on his crew and overhears the McDucks nearby. Karnage haphazardly disguises himself as a botanist to get their help, though the McDucks indulge in his ruse so that he can lead them back to the pirates.
Once the McDucks get the Sun Chaser fixed, they take back to the sky in search of the Iron Vulture. Unfortunately, they run into Dewey's own theatrical (albeit clustered) assault on the aeroplane and they are soon caught inside the Vulture. Still mad at his family for neglecting him, Dewey orders the crew to let the McDucks go with their treasure not willing to see them again, however the beleaguered crew remark on the power of captain going to Dewey's head. The pirates end up forcing Dewey and the others over the edge of the Vulture. Karnage then reveals himself to the pirates and apologizes to his crew for being harsh, while the family apologizes to Dewey for not listening to him. Rallying the pirates back to his cause, Karnage engages in a duel against Dewey, assisted by the rest of the McDucks to confuse Karnage during the brawl. The McDucks escape the pirates by distracting them with a musical number, causing the Vulture to crash into a mountain and Karnage curses Dewey.
Flying back, Scrooge gives Dewey his hat back as reconciliation. Louie also gives Scrooge the sapphire, but it turns out to be a fake that Webby made up to teach Louie a lesson on honesty. Scrooge then ends their adventure listening to Dewey's stories for the rest of the flight.
- David Tennant as Scrooge McDuck, Hat Pirate
- Danny Pudi as Huey Duck, Pirate #1
- Ben Schwartz as Dewey Duck
- Bobby Moynihan as Louie Duck, Pirate #2
- Kate Micucci as Webby Vanderquack
- Beck Bennett as Launchpad McQuack
- Jaime Camil as Don Karnage
- Keith Ferguson as Ugly Mug, Pirate Intern
- Kimberly Brooks as Peg Leg Meg, Hardtack Hattie, One-Eyed Linda
- Sam Riegel as Stinky Boot, No-Name, The Nameless Parrot, Two-Toed Jack
- When Ugly Mug gives Dewey the captain's hat, Stinky Boot is missing the outline below his eyes.
- Webby's eyelashes disappear in the scene of the family reconciling and Karnage's scene following it.
- Before he blows the whistle, Dewey's sleeves are missing.
- Don Karnage and the Air Pirates from TaleSpin appear in this episode re-imagined as singing and dancing pirates.
- The premise was foreshadowed in the first episode "Woo-oo!", as there is a newspaper clipping mentioning the Air Pirates.
- When Dewey is holding a sword, it is a reference to Randy Cunningham as The Ninja with his Ninja Sword from Randy Cunningham: 9th Grade Ninja. They are both voiced by Ben Schwartz.