The park is owned and operated by The Coachman, who made a fortune from his crooked deeds, and is seen in the film when the Coachman brings Pinocchio, Lampwick and a coachload of other boys to the park.
Pleasure Island is a theme park located on an island and is accessed there by ferry. It is implied to be an illegal place as hinted by J. Worthington Foulfellow. The Coachman is apparently the owner of the park and takes all the bad boys that Foulfellow and Gideon captured, including Pinocchio and Lampwick, to the island. Apparently, the boys can do whatever they pleased on the island, such as smoking, drinking alcohol, fighting, wrecking the place and other deeds that good children wouldn't do. The boys were also free of the law and any adults or teenagers who could stop them from being naughty. However, unknown to the boys, Pleasure Island in truth actually serves as a trap. Once the boys had enough time being bad, they would turn into donkeys after they made "jackasses" of themselves. The boys would first grow donkey ears, then a tail, their head would turn furry, having donkey hair, their laughing would then become braying, their hands and feet becoming hooves, before losing their ability to talk (though some donkeys like Alexander can still talk) and then finally being on all fours. The donkeys were then rounded up by the Coachman and his minions. The donkeys were then inspected and those who couldn't talk were stripped of their clothes if they still wore any before being put into crates, then taken back to the ferry that took the boys to the island. They were then sold to salt mines, the circus, etc for money.
Those like Alexander that could still speak were kept behind until they lost their voices or simply used to pull the Coachman's stagecoach. It is implied the donkeys seen pulling the coach were once bad boys that were on Pleasure Island before the events of the film. It is unclear how the boys became donkeys despite being bad. It can be argued that certain beer and cigars were spiked with a magical potion that can turn them into donkeys. For example: Lampwick grew donkey ears after taking a swig of beer and this may have caused a chain reaction that made him into a donkey. Pinocchio threw away his cigar and put his drink aside which may explain why he only grew ears, a tail and brayed. It can also be implied that once a boy reaches a certain level of being bad they turn into donkeys. Lampwick grew donkey ears, a tail, furry head, and brayed after making fun of Jiminy Cricket and teasing Pinocchio when the puppet brayed for the first time. Strangely enough, Pinocchio and Lampwick were the last ones to be the island's victims, but it is likely they avoided the spell as they were playing pool and gambling. It is also unknown how the island got repaired but the Coachman likely got it all mended for its next use.
In Italy, where the original story was written, the donkey is a symbol of stupidity. The moral behind Pleasure Island (or "Toyland" as it was called in the original) is that little boys who scoff at education and moral codes set forth by their parents, preachers and authority figures and instead engage in "jackass" behavior such as fighting, vandalism and underage drinking are often destined to grow up to become men who have no option to make a living except through backbreaking manual labor. And there are plenty of people in the world, such as the Coachman, who will take advantage of that.
Kingdom Hearts 3D: Dream Drop Distance
Pleasure Island appears in Kingdom Hearts 3D: Dream Drop Distance, in the world Prankster's Paradise. It includes various areas of the Island that are found in the original film, like the amusement park. Several new areas that weren't in the original film like the Windup Way, and the Circus tent were included in the game.
- The Donkey Transformation is considered one of the most notably terrifying sequences in Disney history.
- In the model home on Pleasure Island, one of the wrecked things inside was Leonardo da Vinci's famous portrait painting, the Mona Lisa.
- The pool hall is shaped like a giant cue ball with a giant pool stick standing alongside it, a neat takeoff on the giant ball and stick monument from the 1939 World's Fair.
- In the original movie, the curse of Pleasure Island transforms boys who "make jackasses of themselves" into donkeys. In Kingdom Hearts 3D: Dream Drop Distance, this line was reworded as "boys who make jackamules of themselves", most likely to refrain from using a swear so the game wouldn't have a T rating.
- In the original Italian story, Pleasure Island was actually called "Il Paese del Balocchi", which translates as "Toyland". (It can also translate as "Toy Country","Toy Town", or "Toy Village", but "Toyland" is the preferred title.) An early English translation mistakenly dubbed it "Boobieland", the Italian word for "booby" being almost similar to the one for "toy". Also, whereas it seemed to take only a single night at Pleasure Island for the donkey curse to work on its victims, the original Toyland seemed to take a longer period of time, roughly five months.
Characters: Pinocchio | Jiminy Cricket | The Blue Fairy | Geppetto | Figaro | Cleo | Honest John and Gideon | Stromboli | The Coachman | The Coachman's Minions | Lampwick | The Stupid Little Boys | Alexander | Monstro
Objects: Stromboli's Puppets