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 collected by himself from various towns and villages, including Pinocchio, this last one collected by Foulfellow and Gideon, 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. Food, alcohol and tobacco were made freely available on this island. The boys were also free of the law and any parents or cops 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, and other places 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 put his drink aside and threw away his cigar, 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. It can also be implied that the curse can only transform the boys as long as they’re on the island. Lampwick grew donkey ears, a tail, furry head, and accidentally brayed after making fun of Jiminy Cricket and teasing Pinocchio when the puppet accidentally 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 appeared to be the last ones awake, while 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 will engage in "jackass" behavior instead, such as fighting, vandalism and underage drinking and 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.
Many bad boys, including Pinocchio and Lampwick, were taken to the island via stagecoach. Upon arriving, the Coachman ushers them inside and they can do whatever they please on the island, such as fighting, drinking alcohol, smoking, wrecking the place and other deeds that good children wouldn't do.
However, unknown to the boys, Pleasure Island in truth actually serves as a trap. Once the boys have enough time being bad, they would turn into donkeys after they made "jackasses" of themselves. After the transformations, Jiminy Cricket ventures across the island in search of Pinocchio, but the boy sends him away. Jiminy witnesses through a hatch that the donkeys were being rounded up by the Coachman and his minions. The donkeys were then inspected and those who couldn't talk were stripped of their clothes before being put into crates, then taken back to the ferry that took the boys to the island. They were then sold 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.
While Pinocchio and Lampwick are in a bar playing pool, Jiminy tried to warn them about what he's seen, but to no avail, as he was driven out and humiliated. As the boys resume play, Lampwick grows donkey ears after taking a swig of beer and this causes a chain reaction that made him into a donkey. Pinocchio throws away his cigar and put his drink aside, which may explain why he only grew ears, a tail and brayed. Strangely enough, Pinocchio and Lampwick are the last ones to be the island's victims, but it is likely they avoided the spell as they appear to be the last ones awake. Fortunately, Pinocchio and Jiminy make a quick escape into the sea.
The island remains very much similar to the 1940 iteration, however Tobacco Row and references to alcohol were cut, due to it being a made-for-television live-action film in 2000, as well as network censors not allowing alcohol and tobacco references in family-oriented films. In this version it is specifically stated that the Rollercoaster is what causes the boys to instantly transform into donkeys, as witnessed when Geppetto warns Pinocchio who immediately begins turning into one after boarding the coaster's car, and is found fully transformed after passing through the Coaster's doors. It doesn't completely act as a roller coaster, as it stops beyond the doors into a stable where the boys-turned-donkeys are mistreated.
In this crossover comic story, Mickey Mouse, stranded at sea, sees an island in the distance and manages to swim there. He soon discovers that the island is none other than Pleasure Island. The Coachman's fair has fallen into disrepair, some parts of the island having even reverted to a wild jungle; Mickey comments that it seems to have been abandoned for years (confirming that the Coachman did get his comeuppance at some point after the original movie). Mickey faces Maleficent on the island, but the witch is destroyed as the Nothing (a magic phenomenon of unknown origins which provides the main conflict for the story) eats up the whole island. Mickey is saved in extremeis by Dumbo as the last parts of the cursed island fall into oblivion.
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 also included in the game.
Pleasure Island appears in the episode Murder Most Foul. Prince James flees to Pleasure Island to escape from King George who wants him to become a knight. James' real father, Robert, comes to Pleasure Island, and enlists the help of Pinocchio to find James and bring him home to his real family. As they are about to leave, King George arrives.
After an argument between King George and Robert occurs, King George orders his guards to take Robert and kill him, ordering them to make sure it looks like an accident. As the king's men are about to murder Robert, Captain Hook arrives with a few pirates. Hook's men rob the King's men and kill them. Robert believes Hook has saved his life, but Hook says that he can't let him go, as he was a witness to the murders. Robert begs for his life, but is then stabbed by Hook.
In the model home on Pleasure Island, one of the wrecked objects inside was Leonardo da Vinci's famous portrait painting, the Mona Lisa (or more likely a replica).
Assuming the film takes place in the same time period as the original story, late 19th century Italy, certain elements of the park are inconsistent with the film's setting. An example is the Pool Hall: Although billiards in general has a history dating from well before the original story was written, "8 ball pool" wasn't conceived until the early 20th Century.
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 word so the game wouldn't have a Teen 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. The literal translation is "The Land of Toys"). An early English translation mistakenly dubbed it "Boobieland", since the Italian word for "booby" is 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).
The talking statue at the Rough House speaks in a very similar voice to the cartoon character Popeye the Sailor Man, but is voiced by a different actor (he even looks similar in appearance to him).
Apparently, it is not just bad boys from Pinocchio's village that go to Pleasure Island, as the ferry that took Pinocchio and Lampwick to Pleasure Island was full of other boys. This implies that they came from other villages -- but it can be argued the Coachman may have had to make a few trips to the village to collect more boys.