Pleasure Island is a theme park located on an island and is accessed there by ferry. It is implied to be an illegal or extremely notorious place, as hinted by J. Worthington Foulfellow.
The Coachman is the owner of the island and takes all the bad boys collected by himself (or others he hires for the job) from various towns and villages to the island. There the boys are free to do whatever they please, such as smoking, drinking alcohol, fighting, wrecking the place, and other deeds that good children wouldn't do. Food, alcohol and tobacco are made freely available on the island. The boys are also free of the law and any parents or cops who could stop them from being naughty. Essentially, the island is designed to be the perfect bad boys paradise.
However, unknown to the boys, Pleasure Island actually serves as a trap. Once the boys have spent enough time being bad, they begin to succumb to a deadly curse that exists over the island (presumably planted via dark magic by the Coachman himself) which turns them into donkeys due to making complete "jackasses" of themselves and behaving like destructive animals. The boys first grow donkey ears, then a tail, their head turns furry with donkey hair, their laughing becomes braying, their hands and feet become hooves, they lose the ability to talk (though some donkeys like Alexander can still talk), and then finally go on all fours. The donkeys are then rounded up by the Coachman and his minions and inspected. Those who can no longer talk are stripped of their clothes and thrown into crates and then taken back to the mainland via ferry and are finally sold by the Coachman into hard labor in salt mines, at the circus, and possibly other places for money. The few donkeys who retain their voices however are not shipped with the others and are presumably kept by the Coachman until they too completely lose their voices or are possibly disposed of to prevent them from warning other victims who come to the island.
The exact way the curse is placed over the island or how it turns the boys into donkeys is unknown though it appears that it only takes effect once the boys have committed enough bad behavior. There appears to be no way to stop it once the transformation begins and appears to be permanent, as even remorse for their actions doesn't reverse the effects and Pinocchio's donkey ears, tail, and bray in his laugh did not disappear until he was later revived by the Blue Fairy. It appears to work slower for some individuals as both Lampwick and Pinocchio showed no effects of the curse until long after the other boys possibly due to the fact they relaxed for a while playing pool. It also remains unknown how some of the boys are able to retain their voices while others aren't, though it possibly depends on the severity of their misdeeds. It is apparent that the curse can only work on transforming the boys while they’re on the island, as after Pinocchio escaped, he underwent no further transformation.
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.
Meanwhile 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 before the donkey transformation on Pinocchio could go any further.
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 Blue Fairy's magic appears to be the only way to undo the curse of Pleasure Island as Pinocchio's donkey ears and tail completely disappeared when he was revived by her.
The pool hall is shaped like a giant 8 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, said to be located in Cocagne, was actually called "Il Paese dei 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, in the original story the transformation is caused by a disease that affects people who never study (in Italian culture, the donkey is symbolic of ignorance, stupidity and goofiness) and 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.
Interestingly, no girls are taken to the island, just boys. The reasons for this could be that boys can be more destructive and are more likely to be enticed by troublesome behavior than girls are.