Once upon a time, Disney had no place to go for after hours entertainment. There were a few hotel bars around Lake Buena Vista properties but nothing that stood out.
Orlando had Church Street Station, with its complex of bars and its night life atmosphere, and people would flock up there after the parks closed.
Disney saw lost opportunities, and announced Pleasure Island, with its own complex of bars and it opened to great fanfare. The bars were packed and live bands played on outdoor stages to large crowds. All was good.
Over time - and I'm sure someone here knows the reason - Pleasure Island lost its edge as the place to be. The crowds stopped coming. The outdoor band played to no-one. Inside the bars, there were no people. The Adventurer's Club - intended to be a place where you could take a break from the dance scene - became one of the most popular venues.
To avoid the embarrassment of having an outdoor stage with no-one wanting to listen to the band, the stage was removed. To try and boost attendance, the cover charge for entrance to Pleasure Island was replaced with a policy that required one only to pay for individual clubs they entered.
So, what is Pleasure Island today? :shrug: It certainly is not what it once was. Perhaps it is better than what it had once become. That seems to be the nature of night life in Orlando. Church Street Station failed, too.
My advice to the original poster - don't make going there the highlight of your night. Instead, plan to stop by Raglan Road for the Irish Pub atmosphere while you enjoy a pint, or go to the Adventurer's Club for its signature drink, a Kungaloosh, and plan to stay for an hour or so to determine whether its quirky atmosphere is for you. See if a good band happens to be playing at the House of Blues the night you will be there, or otherwise, plan to enjoy some shopping at Downtown Disney, with a trip through Pleasure Island for a drink.
Whatever you do, I hope you have fun. :wave:
Or just go to Citywalk! :lol: