With the Grand Festival behind them, Ash and friends are headed for Ever Grande City and the Hoenn League Championships which are a mere two weeks away. At the docks of Slateport City, Ash, Max and Brock await May’s arrival. Brock tells Ash and Max that you can’t rush a girl when she’s shopping. A shout calls to them and they turn to see May running towards them, flashing what appear to be tickets. She tells the others that she won airline tickets to Ever Grande City.

They board the aircraft and it takes off. A woman emerges from the cockpit and tells them that she hopes they have a good time on their long flight and that they’ve made a slight change in plans - they’re heading for Team Rocket Headquarters instead of Ever Grande City. She throws off her costume to reveal she is Jessie as the door to the cockpit opens. James and Meowth lean out of their seats and Meowth tells them that Operation Raffle Racket was a success. Bars block the gang from getting out of their seats and Ash tells Pikachu to use Thunderbolt.

The electric mouse jumps from the top of the seats and releases a Thunderbolt just as an electric-resistant ball traps it. Jessie informs everyone that she spent everything to make the trap successful - including their stash of money and James’ bottle cap collection. James whimpers about the caps and Meowth cries over the money for food. While they whine and Jessie continues to bask in the glory of success, the plane begins to rumble.

James retakes the controls and stabilizes it. He checks the gas and finds it empty. He yells at Jessie that she was supposed to buy fuel. She remarks that she did and points to one measly oil drum of gas. The plane begins to rumble as it flies through a cloud. James and Meowth steer the plane towards the nearest spit of land, a small island in the middle of the vast ocean.

The impact of the landing springs free Ash and the others and they disembark from the plane. Nearby, the bushes rustle and Max spots something hairy. He thinks it is a Venonat until it stands up fully and tells them it is a human. The man tells them his name is Robin and thinks they all came to help him. Jessie and James get off the plane and tell him that they are the ones that need help.

Later, Robin tells them the story of how he got to the island. He was a traveling salesman for a Multi-National Corporation and he used to travel all over the world by boat. One day, he got caught in a violent storm. Everyone on board was evacuated safely except for Robin. No one saw him as he fell overboard. A Wailmer saved him and when he awoke, he found himself on the island - Wailmer Island, which he dubbed himself.

Suddenly, a Wailmer emerges from the water nearby. Ash quickly pulls out his Pokédex and looks it up. Once the Dex stops talking, Wailmer sends out a spout of water - a Water Spout. Team Rocket decides that they aren’t going to stick around on the island any more so they begin to swim out to sea. Before they get too far, though, they get caught in a whirlpool. They get sent into the air and Wailmer catches them, taking them back to the land. Robin explains that the island is surrounded by whirlpools that can smash rafts, as he once experienced when being pulled by Wailmer. With the whirlpools blocking the island, no access from outside ships is available. Team Rocket goes into an outrage as Ash realizes that if they are stuck there forever, he’ll never make it to the Hoenn League.

Brock tells them that they can convert the plane into a ship. Max asks the obvious question - where to get fuel. Robin answers that they can use trees to make fuel. And so they all get to work. While Combusken heats the metal to make it pliable, Corphish shapes another piece and once it is ready, Glalie and Mudkip cool it with Ice Beam and Water Gun. Brock and Ludicolo carry the metal to Ash, Pikachu and Torkoal who put the boat together and weld it. Meanwhile, Swellow, Beautifly, Grovyle, Bulbasaur, Robin, May and Max get wood and stockpile it in a barrel. Forretress squashes it to make a liquid. And for the fun of the group, Skitty plays with Wailmer.

Up on a hilltop Bellossom, Skiploom, and Sunkern dance and float while watching everyone working down below. Behind them, Team Rocket works on picking vegetables. James likes the job, thinking about the fresh air, good times, and a lot of fun. He exclaims that the island it great but Jessie disagrees. Her and Meowth get angry and plan to steal the boat once it’s finished and just leave the others while they sail on to Headquarters.

That night, the boat lays finished in the water and everyone gathers in the cave to eat dinner. Beautifly, Grovyle, Swellow, Glalie, Bulbasaur, Corphish, Torkoal, Forretress, Mudkip, Pikachu and Skitty eat the Pokémon food from Brock while the others eat over a little ways. Max wonders where Munchlax is so May calls it out. It heads straight for the food bowls but Max whips out May’s Pink Surprise and it promptly falls asleep. Robin says that they’ll shove off the next day and Team Rocket begins to act very nicely. May and Max get suspicious but nothing happens so they head off to bed.

Very early the next morning, Pikachu wakes up early under its leaf. Ash, too, wakes up and wonders where Robin is. They find him on the beach saying goodbye to Wailmer, as it will be staying on the island. He tells the gang that before he came to the island, he was work 24/7 and that he was going through the motions, like sleepwalking. But, living on the island with Wailmer, he found the joy in life and he came to love Wailmer. Max suggests that he bring the Ball Whale Pokémon with him. Wailmer likes the suggestion but Robin wonders what a Wailmer would do in the city.

Suddenly, a claw grabs Pikachu. Everyone looks to the boat to find Team Rocket with the mouse. They do their motto once again and then set out with the ship. Pikachu fires a Thunderbolt at them but they have an electric protected cage again. Brock tells them it isn’t time to go but they don’t listen and keep sailing. They sail towards the whirlpools and the boat stops. With no gas, Jessie and James had no control over the boat and the whirlpool pulled them in again. The force of the whirlpool broke the boat and sent Team Rocket and Pikachu flying. Team Rocket landed in the water near the island while Pikachu continued to soar.

With some quick thinking, Ash jumped on Wailmer and saved Pikachu. Once back on land, Jessie and James sent out Seviper and Cacnea, who hugs James. Jessie orders Seviper to use Bite while James tells Cacnea to use Pin Missile. Wailmer uses a Hydro Pump to block the attacks. Pikachu uses Thunder and Team Rocket falls in the water again. They decide to use Wailmer as a getaway. They climb on to cries from Robin that it can’t carry that much weight.

Wailmer begins to glow and evolves into a Wailord, which Ash looks up in his Pokédex. Wailord uses a Water Spout attack to sends Team Rocket blasting off again. Wailord carries everyone out to sea; the whirlpools approach quickly. Wailord pushes through them and as it does, a giant wave crashes towards them. Wailord uses Water Pulse to smash it and they get past the whirlpools.

A short time later, a boat spots them. The captain tells them to stop the engines. Everyone climbs aboard and they thank the captain for seeing them. Robin turns to Wailord to say goodbye but he can’t bring himself to do and jumps back to the Whale. He explains to the gang that living on the island showed him what life was really about. In the city, he never felt that way and there is nothing for him there. He finishes by saying that the island has everything. With that, he and Wailord set off for Wailmer Island as Ash and the others wave from the ship.