The history of speakeasies has become a charming nod to the spirit of American
rebellion. It’s crazy to think that there was a time when alcohol was not only discouraged but completely outlawed. During prohibition this was precisely the case. Speakeasies, or illegally run locations where one could obtain alcohol, were havens for people who still craved the fun of imbibing in public. Usually requiring a password or other method of selective entry, these secret-not-so-secret spots were prevalent in almost every major metropolis and small town in the country throughout the prohibition era.
As a burgeoning city in the 1920’s, Orlando was no exception. Records indicate that there
were multiple Orlando speakeasies during prohibition which were secretly open for business (and indeed quite busy!). Sometimes masquerading as ordinary soda shops, these speakeasies were a way for the city-folk who weren’t hiding moonshine under their floorboards to get a drink. The Flamingo Cafe was a special little gem. Originally a soft drink stand called the Orange Drop, the remolded Flamingo Cafe was a haven for people fond of libations and gambling. The cafe included a famous back room where cards, dice and roulette wheels spun for the entertainment of its guests. It operated just outside city limits (near what is now Executive Airport) and was impervious to infrequent raids, often being open for business despite having been shut down just nights before.
Orlando has brought that secretive feel back into the 21st century with several local
“speakeasies” that not only require a few extra hoops to enter but will transport you back to the era when night life was a saucy secret. Downtown Orlando has some of the most authentic feeling ones, nestled into buildings that have been standing for a century or longer, giving you the pleasure of a cramped squeeze through a dark hallway before entering a big, open room buzzing with booze and fun. Hanson’s Shoe Repair is a local favorite. It sits in the historical building 27 E Pine Street, and the vibe is not only old-timey but also a little exclusive—obtaining the password, while easy enough (it’s posted daily on Twitter), makes you feel a little bit more like you’re doing something naughty. Also located in downtown Orlando, Mather’s Social Gathering is another historical spot with a nostalgic feel located on Magnolia Avenue. It doesn’t require a password but has some house rules that require adhering to (and who doesn’t love giggle water?). Both The Treehouse and The Courtesy boast a bounty of craft cocktails, and the latter offers classes on how to make them yourself at home, moonshine not included. So, while imbibing nowadays is easy enough, you can still have fun pretending that you’re doing something a little illicit – even in the home of Mickey Mouse.