Role in the series
Skybird Island first appeared in the episode "Birds of a Feather" where Winger meets Skully and learns that she is a princess. Jake and his crew were atop Skull Rock watching the various parrots flying around socializing. A parrot named Winger meets Skully and asks him if he can help her find the Skybird Kingdom. Skully informs Jake and the crew is off. When they finally reach it, Winger meets the Wise Old Parrot; ruler of the kingdom. He informs Winger that she is the lost princess of the kingdom. She is crowned and the kingdom begins to rejoice. That all ends when Captain Hook arrives and steals her crown. Jake, Skully and Winger chase after the captain eventually defeating him and restoring peace to the Sky Bird Kingdom.
Skybird Island reappears in the episode "Skybird Island is Falling!" Here, Winger and Skully are enjoying each other's company eventually coming to the island's magic golden tree. Skully and Winger learns from the Wise Old Parrot that the island will plummet to the Never Sea without the tree's golden leaves. Winger then watches helplessly as the leaves are stolen by Captain Hook and his pirates, for Hook wants them. Jake, Izzy and Cubby appear to save the island to little avail. Winger and Skully eventually gathers the island's natives and attack Hook stealing the leaves back in the process. Although the leaves are back in Winger's possessions, they may not be able to put the leaves back in time. Thankfully, Izzy's pixie dust is able to restore the leaves onto the branches. After the pirates return to Pirate Island, Winger sends a thank you message hoping to see the pirates again soon.
Skybird Island reappears in the episode "Sail Away Treasure", after locating the treasure hidden on Never Peak. Jake and his crew soon became curious to find out what was hidden in the treasure chest and who the flying ship belong to they soon found a clue leading the young pirates back to Skybird Island were they were greeted by Winger and Wise Old Parrot. Wise Old Parrot revealed he was once the captain of the flying ship. Captain Hook and Mr. Smee soon arrive and attempt to steal both the treasure and the ship but Hook's greed was the instrument of his own undoing when he discovered the treasure was merely a whistle. Unknown to Hook, the whistle summons the Feathered Four, the royal protectors of Skybird Island who swooped down and carried Hook off. In a attempt rescue his captain, Smee pulls the wrong lever retracting the ship's wings, sending Smee and the Leakey Beak falling from the sky only to be rescued by Izzy and her pixie dust. Thwarted yet again by Jake and his crew, Hook and Smee head back to the Jolly Roger. Skully along with his mates return the Leaky Beak to Wise Old Parrot who gives the ship to Skully.
In the episode "Play It Again, Cubby!", Jake and his crew venture to Skybird Island to ask princess Winger if she knew the rest of the song stuck in Cubby's head.