Ash and the gang discover a new island that is loaded with different types of fruit trees, and since the food there is free they decide to take a day off and give their Pokemon a little vacation. Unfortunately, Team Rocket doesn’t take a day off from trying to steal Pikachu… will they catch our heroes off guard.

Ash and Tracey are thrilled when they reach Murcott Island, an island famous for having tons of bug-type Pokemon. Misty must try and overcome her fear of bugs when the trio finds an injured Scyther in need of treatment. Meanwhile, Team Rocket gets into their own battle with a swarm of Scyther, and they come out of it with a whole new look!

Team Rocket has engine trouble and lands on an island where the natives are waiting for the Great Meowth of Bounty to arrive and fulfill an ancient prophesy. When Meowth gets mistaken for this great creature with special powers, he enjoys the special treatment and decides to play along. But, when he’s unable to perform the ancient ritual that’s expected of him, the treatment he gets isn’t quite so fun anymore.

Ash, Tracey and Misty find more excitement than they bargain for when they reach their next destination. Professor Oak tells them that divers have recovered an Orange League Championship trophy off the coast of Moro Island that dates back over three hundred years! The trophy is on display at the Moro Island Museum of Art for all to see. By the time they get to the museum, Team Rocket has already paid a visit and now it’s up to our heroes to track them down!

While Ash and friends are still discovering new islands, they come upon the seven Grapefruit Islands where groves of giant grapefruit are ripe and in season. When it looks like thieves are stealing the grapefruit, Ash, Tracey and Misty volunteer to help catch them. Surprisingly enough, what looked like hundreds of thieves was actually just one giant, hungry… and sleepy culprit!

A second Orange Islands trainer puts Ash and his Pokemon through a battery of tests. First, Ash must climb a mountain without use of his Pokemon. Once at the summit, he must assemble the proper team of Pokemon to freeze moving water, construct a bobsled, and then win a race on the sled. Do Ash and his Pokemon have enough skills for the challenge of Orange Island training?

While sailing between small islands, the group encounters an extremely busy Nurse Joy. She tells the group that she travels from island to island helping sick and injured Pokemon, and invites our heroes to travel with her. On the expedition, they learn much about Pokemon and Joy’s very special friendship with a Magikarp. Unfortunately, Joy runs some into trouble continuing her rounds once Team Rocket storms into the area!

Misty meets another female trainer who also is an expert on water Pokemon. The new trainer notices some signs that Misty’s Psyduck may be ready to evolve. As the two prepare for a Pokemon battle, a Golduck springs from the water and battles for Misty. With her powerful new Pokemon, can Misty defeat both her newfound friend and Team Rocket?

Ash, Misty, and Tracey buy tickets to the Pokemon Showboat, a wonderful carnival where Pokemon can speak and perform plays! A young actress from the performance has been having problems with her Raichu ever since it shocked her early in their relationship. Ash and Pikachu may be able to help. Of course, they’ll have to deal with Team Rocket first, as they attempt to steal all the talking Pokemon.

Aboard Lapras, the group follows a news crew to an uninhabited island, where a scientific expedition is underway after the discovery of a fossilized Kabuto. A series of natural disasters place our heroes in mortal danger, with only the power of their Pokemon to help them. What is the secret of the Kabuto, and who wants that secret to remain hidden?