The Best Speakeasies In Orlando & Beyond

Sshhhh…I have secrets to tell you. I’m going to share some of my favorite speakeasies and hidden bars in and around Orlando with you! Each of these hidden bars is uniquely themed, dimly-lit, and is full of handcrafted cocktails.

Some of these bars are not the ‘traditional’ speakeasies you might be thinking of…but they are all wonderfully themed and take you on a fabulous journey away from your day-to-day.

1. Crown Alley – Lake Mary, Fl

Crown Alley is located in Lake Mary, Fl and is hidden on the side of The Grafton Street Pub. Look for the red phone booth…that’s also the entrance!

This spot is one of my favorites and here’s why: Easy to get to, plenty of parking, amazing cocktails, delicious food, and the atmosphere is beautiful.

They are open Tues-Sat at 5pm. Happy Hour is 5-7pm daily. This is a popular spot (especially at happy hour) and it will fill up on the weekends! Reservations are available click here.

We love Crown Alley, click to read more abut this favorite spot!

2. Mathers Social Gathering – Downtown Orlando

Mathers Social Gathering is a stunner…and is possibly one of the best speakeasies in Orlando. It’s located Downtown Orlando and ticks all the boxes of a quintessential speakeasy.

It’s even located inside a 130 year old building…which perfectly sets the scene for this prohibition era bar. And you must enter through a bookshelf (door)! Once you’re inside the smell of worn leathered couches fills your nose, awe…the perfect spot to sip your libations!

The cocktails and food are worth coming to check out. As I mentioned, this spot is downtown, so parking is not the easiest. I also need to mention, on Tues 8-10pm and Sat. 10-12am they have a Burlesque show….which may or may not be your thing.

Hours are Tues-Sat. 4pm-2am and Happy Hours are 4-7pm

3. The Imperial – Orlando & Sanford, Fl

The Imperial is located inside of Washburn Imports. Home to exotic and unique furniture, imported from various locations around the world. They have two locations one in Orlando and the other in Sanford. This may not be what comes to mind when you think of a speakeasy, but since this is a bar located inside a furniture store, I think it counts!

Both locations offer delicious food. The Orlando location is larger and even has an outside patio and features beer and wine with hours being: Wed-Sat. opening at 5pm. The Sanford location has a full bar with unique cocktails, hours are: Tues-Fri opening at 5pm and Sat-Sun opening at 2pm.

4. Deland Cocktail Company – Deland, Fl

The Deland Cocktail Company, aka Hemingway’s Lounge, is located inside The Deland Hotel. This historic hotel was built in 1925 and houses this ‘speakeasy’ feeling bar.

This small bar is enveloped with dark wood walls and a brick fireplace, which makes this spot cozy and romantic. The menu is full of unique cocktail creations and a wide variety of food offerings.

Hours are Wed-Sun 4pm-10pm

5. Suffering Bastard – Sanford, Fl

Grab your Hawaiian shirt and head to Tuffy’s Bottle Shop in Sanford. There you will find the enchanting ‘hidden’ Tiki Bar…Suffering Bastard. This ‘speakeasy’ is a bar inside of a bar and is the quintessential tiki bar! Donn Beach would be proud! (The Godfather of the Tiki Bar)

This bar is in downtown Sanford, so it’s easy to get to and has plenty of parking near-by. Hours are Wed-Sun. opening at 5pm.

This fun spot fills up fast on the weekends, so you may want to grab a reservation: HERE

Another favorite Tiki Bar of mine is Permanent Vacation in Maitland, Fl. It could also be on this list, since it also is a bar inside of another bar.

6. Enzo’s Hideaway Tunnel Bar – Disney Springs

If you know me, you know i’m a Disney person….so I have to share one of my favorite spots at Disney Springs….Enzo’s Hideaway! This is the perfect spot to escape the heat and the crowds at Disney Springs.

This hidden ‘rum-runners’ tunnel is a throw-back to an ‘Italian’ 1920’s era and has two entrances. The main entrance is under Maria & Enzo’s Restaurant. Just look for the big sign, it’s Disney, they want you to find it! The other is through a backdoor inside of The Edison…which makes you feel like you’re doing something sneaky.

Here’s a video of the back-way entrance, which is my favorite way to arrive!

Their prohibition-era cocktails paired with Italian dishes are sure to please! It’s always at the top of my ‘Disney’ list when I want to escape the crowds and heat!

They are open daily at 11:30.

* If you’re making a trip specifically to try this spot, the Orange garage will be closer. However, if you’re spending the afternoon, the Lime garage is my go-to since it’s more centrally located at Disney Springs.*

Let me know in the comments. Thanks for reading!

Xx Autumn

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