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We’re Sharing Our Favorite Speakeasies In Orlando You Have To Check Out This Weekend

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Shh… can you keep a secret? We’re sharing our favorite speakeasies in Orlando you have to check out this weekend! Orlando has so many cool bars and restaurants, but we’ve found some of the most secretive and hidden spots around town so you don’t have to!

Keep reading to discover Orlando speakeasies, as well as how to get inside!

Number one on our list has got to be the iconic Hanson’s Shoe Repair nestled in the heart of downtown Orlando. Located on the third floor, this rooftop bar allows you to see beautiful views of the city, but also has an amazing ambiance of a 1920’s bar inside.

The building itself is known to be one of the oldest buildings still standing in downtown Orlando and originally was a shoe repair shop. To get the daily password, you’ll have to check out their social media, or call/text 407-476-9946.

Daily | 8PM–2AM

📍27 E. Pine St. Orlando, FL 32801

Another super secret spot in Orlando is Mathers Social Gathering! Mathers offers a sophisticated, yet comfortable setting with stylish dark wood and exposed brick walls remnant of the late 1880s. Enjoy boutique spirits and classic cocktails, or maybe even try their bathtub gin.

Select nights are burlesque-themed, and social hour is from 4PM–7PM. The building is an old furniture store that predates the 1884 Orlando fire, and the bar is located on the third-floor hideaway house. Fingers crossed you can find it!

SUN–MON | Closed

📍30 S. Magnolia Ave. Orlando, FL 32801

A tiki bar hidden inside of another bar? Sign us up! Suffering Bastard Tiki Bar is an intimate tiki experience located inside Tuffy’s Bottle Shop in the Historic Downtown Sanford! With over 35 craft cocktails to choose from served in tiki glasses, you definitely won’t be suffering at Suffering Bastard Tiki Bar.

The secret door in the back of Tuffy’s opens at 5, but the bar is small and cozy so you’ll want to get there early to secure your spot! While you’re there you can also check out their tropical food options like crab rangoons, chicken skewers, and Haupia pie.

MON–TUES | Closed
SUN | 5PM–10PM

📍200 S. Myrtle Ave. Sanford, FL 32771

Located in a storied rum runner tunnel under Maria & Enzo’s restaurant at Disney Springs, Enzo’s hideaway is the perfect speakeasy that pours prohibition-era cocktails and serves classic Italian dishes. This hidden tunnel bar is known for its hospitable bartenders, swinging music, and humorous graffiti.

If you’re looking for some old-fashioned giggle water, why not try their hazelnut old-fashioned, limoncello gimlet, or Enzo’s smash. They also have a smuggled and stashed collection of unique, hard-to-find spirits that will be sure to jazz up any drink. Also, be sure to check out their dessert and after-dinner cocktails, yum!

Daily | 4:30PM–10PM

📍1560 East Buena Vista Dr. Lake Buena Vista, FL 32830

Comic book shop by day, speakeasy bar by night, The Geek Easy in Winter Park is perfect for all those nerds at heart who just want to enjoy a good drink and talk about some amazing comic books. The Geek Easy is also a great hangout spot where you can dance to DJ music, play board games, or participate in a trivia night!

Everyone is welcome to geek out at The Geek Easy and there are so many different events each week to choose from. Whether it’s karaoke, open mic night, Sailor Moon burlesque, K-Pop Rave, or heroes and villains, there’s something for everyone to enjoy!

SUN | 9:30PM–2AM

📍114 S. Semoran Blvd. Suite 6 Winter Park, FL 32792

Have you ever been furniture shopping and needed a drink? Well, now you can at the Imperial Wine and Beer Garden! Imperial Wine Bar has 3 locations around Orlando, and they can all be found inside the beautiful Washburn Imports furniture store. With over 35 beers and 35 wines to choose from, the Imperial has something for everyone to enjoy!

While enjoying your wine or beer in the garden, you’ll notice that most of the vintage furniture pieces are for sale, and offer some unique places to sit and hang out with friends!

MON–TUES | Closed

📍Orlando: 1800 N. Orange Ave. Orlando, FL 32804

📍Winter Park: 170 E. Morse Blvd. Winter Park, FL 32789

📍Sanford: 116 E. 1st St. Sanford, FL 32771

Remember that secret treehouse you had as a kid? Well, now you can enjoy cocktails and spirits in Orlando’s coziest treetop bar! The Treehouse is located right in downtown Orlando, and is inside the “green doors where two trees meet”. 

The Treehouse Orlando is the perfect place to start your evening with their gorgeous tree-lined backdrop and neon signs for the ultimate Instagram picture. Take the green stairs to the top floor and enjoy the secret hideaway in downtown Orlando!

SUN–TUES | Closed

📍68 E Pine St, Orlando, FL 32801

High-quality cocktails, whiskies, and craft beers, The Woods is a hidden bar in Orlando that is located on the second floor in the old Historic Rose building right by Wall Street. The Woods strives to give you only the best ingredients for food and drinks including local distilleries and breweries.

You can also enjoy their happy hour on weekdays from 5PM–8PM, and other weekly specials including $1 drafts on Tuesdays, free bacon Wednesdays, and live music Thursdays! They also have cocktail classes where you can learn how to mix it up behind the bar!

SUN | 4PM–12PM

📍49 North Orange Ave. Orlando FL, 32801

Located inside Gods & Monsters, Vault 5421 is a post-apocalyptic themed craft bar that specializes in beers, ciders, meads, themed cocktails, and shots. Gods & Monsters know it’s tough out there dealing with the alternate timelines and end-of-the-world mayhem in Orlando, so they’re happy to serve you and your cosplaying friends.

Vault 5421 also has free-to-play board games and retro video games to bring you back in time. Be sure to check out their social media for happy hour deals, cage dancer appearances, and adult game nights.


📍5421 International Dr. Orlando, FL 32819

Last but not least we’re ending our speakeasies in Orlando list with Propag8 Windermere! Located in The Grove right next to Feather and Quill, this bar is perfect for plant lovers and cocktail lovers alike. Propag8 specializes in scotch, whiskey, and mezcal cocktails, and always has a rotating drink of the night!

Not only can you enjoy amazing drinks, but they also have delicious bites from the kitchen next door. Be sure to keep up with their Instagram, as that’s where you’ll find the password to this plant-filled bar every night!

SUN–WEDS | Closed

📍The Grove Dr. Orlando, FL 34786

Speakeasies in Orlando

The secret is out! Next time you’re at one of these Orlando speakeasies don’t forget to follow and tag us @StuffToDoInOrlando!

Kimberly Gooch

Kimberly Gooch

Hi I'm Kim! I am a Florida native from Clearwater Florida, and now currently living in Orlando. I've been in Orlando for the last 6 years and love to explore everything the city has to offer. I travel a lot on the weekends visiting new cities, and in my spare time I enjoy hiking, biking, kayaking, and discovering new things to do.

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