Josh Martin finally manages to get a date with a girl he's been chasing the whole school.
Year, but his father has won his company's sales contest and the family will go to Walt Disney World instead. Josh must escort his little brother, George, through the park while his parents attend the sales convention functions.
While waiting in line at Space Mountain, Buzz Light year presents Josh with a pin and suggests he'll enjoy the ride a lot more now. Josh and George board the sled, but Josh doesn't notice the cast member pushing a button on the sled. As they start the ride, Josh is suddenly propelled into another dimension where he's the commander of space ship. The ship is a battle cruiser, and receives an order to rescue a princess who has been kidnapped by pirates. With the help of the ships executive officer and his staff Josh develops a plan to accomplish the rescue.
Josh manages to rescue the princess, but it seems like the adventure has consumed several days. He wonders what's happened to him back on the ride and awakens to find the ride just ending. He doesn't know what to think of the experience, but he's glad he had it. As Josh and George leave the ride, they encounter a girl Josh is sure was a character in his dream adventure. She doesn't acknowledge and connection to Josh's adventure, but she wears a pin like his.
George want to go to Pirates of the Caribbean next, but Josh convinces him to stop for ice cream on the way. At the ice cream stand a group of girls appear, and one is wearing the pin. Josh engages her in conversation, and they share their strange experiences. She's been on Pirates of the Caribbean and is headed for the Jungle Cruise. They wonder if they'll meet in the next dream adventure, if they experience one.
On Pirates of the Caribbean Josh finds himself as a crew member on a pirate ship. In Ari's last adventure she was a princess kidnapped by pirates and rescued by a Navy Captain. Josh is confused since he's only a common sailor and despairs of rescuing Ari. The pirate ship captures another ship, and a princess is aboard, but she's not Ari. When the pirate ship docks at Tortuga Josh looks for Ari, but he doesn't find her. He sees another pirate captain dragging a black slave girl into a house and hears a scream. He investigates and discovers the girl is Ari. He rescues her from the pirates and they plot an escape. As they reach the docks, hoping to commandeer a boat, the Navy arrives to rescue the captured princess. The adventure ends there, and once more Josh is back in the real world. He meets with Ari at the ice cream stand, and they get better acquainted. They are both from Atlanta and agree to meet back home.
In Atlanta they get together and discover a side effect of their experience is a bit of mental telepathy.
