When was the last time you went to a Speakeasy? It’s been too long. Thankfully, Orlando actually has a cool prohibition inspired hangout. Oh ya. It’s time for the fun drinks.

Beautiful prohibition era cocktails

Head to NV Art Bar on Pine Avenue downtown, and go upstairs to the door that looks foreboding with the tiny window on it. You’ll need to give a call to Hanson’s Shoe Repair at the following number: (407) 476-9446. You usually have to leave a message, then you’ll get a text back with the password. We like to call as soon as we leave our house and drive over, as it can take about 5 minutes to hear back.

Beautiful rooftop seating at Hanson’s Shoe Repair – AKA the cool speakeasy bar in Downtown Orlando

Sunday night is my favorite. Head upstairs and lounge on the roof top garden. It’s chilled, and they usually have a nice wait to get drinks, but the soundtrack for whatever music is playing is usually the perfect mix of the National, Tom Waits, and some fun Chet Baker or Dave Brubeck.

The drinks have at least 8 ingredients each, and they are made to be culinary and alcoholic delights. The bartenders take their time. But you’re not here to rush. Enjoy, chat, and savor something delicious. Image you’re back in time. Enjoy a nice conversation on the roof.

I haven’t had drinks that good outside of New Orleans, where I recently discovered some of the best cocktails in the country. It’s my favorite bar in Orlando, and I’m a snob for good atmosphere. Skip Pleasure Island (for the love of your sanity!) and enjoy a real experience here. It’s fun times, and worth every delicious cent you tip these skilled bartenders.

Hanson’s Shoe Repair (And Speakeasy Bar)
27 E. Pine St.
Orlando, Florida 32801