Sshhhh… I have secrets to tell you! 🤫
I’m sharing my absolute favorite speakeasies, hidden lounges, and secret bars in and around Orlando! Each one is uniquely themed, dimly lit, and serves incredible handcrafted cocktails.
The Best Speakeasies In Orlando (& Beyond)
Some of these aren’t the “traditional” Prohibition-era speakeasies you might be picturing… but they are all wonderfully themed and take you on a fabulous little escape from your day-to-day. Whether you’re sneaking through a secret bookshelf, ducking into a disguised phone booth, or slipping behind a hidden door, these are the best places in Central Florida to sip something special!
1. Crown Alley – Lake Mary, Fl
Tucked right beside The Grafton Street Pub, look for the classic red London phone booth… that’s your secret doorway inside!
This spot remains one of my top favorites, and here’s why: it’s super easy to get to, has plenty of parking, serves amazing cocktails, offers delicious food, and the atmosphere inside is stunning.
- Hours: Tuesday–Saturday starting at 5:00 PM. Happy Hour 5:00 PM–7:00 PM daily.
Pro-Tip: Super popular (especially during happy hour), fills up fast on weekends – snag a reservation ahead of time!
We absolutely love Crown Alley! Read our full review here: Crown Alley Lake Mary: A Fabulous Speakeasy Lounge
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.
- Hours: Tuesday–Saturday, 4:00 PM–2:00 AM (Happy Hour 4:00 PM–7:00 PM). Burlesque performances Tuesday 8-10 PM and Saturday 10 PM-12 AM.
3. The Imperial Wine Bar & Furniture Store – Orlando (Ivanhoe Village)
The Imperial is uniquely situated inside Washburn Imports on N. Orange Ave in Ivanhoe Village. Home to exotic, one-of-a-kind furniture imported from all around the globe, this spot transforms into a vibrant boutique wine and craft beer lounge by night.
- Hours: Wednesday–Saturday starting at 5:00 PM.
Washburn Imports – The Imperial
Perfect for a cool evening – pair it with a stroll through Ivanhoe Village. See my Best Things To Do In Orlando Besides Theme Parks for more interesting things to do.
4. DeLand Cocktail Company – DeLand, FL
Located inside the historic DeLand Hotel (built back in 1925), DeLand Cocktail Company (formerly Hemingway’s Lounge) feels like stepping straight into a warm, vintage novel.
Enveloped in dark wood-paneled walls, brick accents, and a cozy fireplace, this intimate lounge is ideal for a romantic date night. Their mixologists create rotating craft menus using elevated ingredients paired with tasty small bites.
- Hours: Wednesday–Sunday, 4:00 PM–10:00 PM.
5. Suffering Bastard – Moving Soon to Mills 50 (Orlando)!
Big news for my fellow tiki lovers! The iconic, intimate tiki lounge Suffering Bastard officially closed its Sanford doors inside Tuffy’s on April 30th 2026 and is packing its tropical bags for Orlando!
Owners Arthur Booth and Julian Burgos (the minds behind Death in the Afternoon and Lorelei Wine Bar) are relocating Suffering Bastard right into the heart of the Mills 50 District! They are transforming the former Balloon World building at 828 N. Mills Avenue into the ultimate neighborhood tiki hideaway.
Why We’re Excited: Bringing Donn Beach-worthy tropical mixology, custom mugs, and moody exotica decor into Orlando’s coolest neighborhood makes this one of the most anticipated bar debuts on the horizon! Stay tuned as we share opening date updates.
Status: Moving to Mills 50 (828 N. Mills Ave, Orlando). Expected to reopen late 2026 / Q1 2027.
Another favorite Tiki Bar of mine is Permanent Vacation in Maitland, Fl. If you go get the Banana Daiquiri….it’s delicious!
Always stay up to date with the best of Orlando food, theme parks, and hidden gems by following me @FlamingoInFantasyland
on Instagram!
6. Enzo’s Hideaway Tunnel Bar – Disney Springs
If you know me, you know I’m a total Disney girl at heart! This hidden “rum-runner” tunnel is a throwback to a 1920s Italian prohibition spot. Enter through the main stairs beneath Maria & Enzo’s Ristorante, or sneak in through the secret back-door connection inside The Edison.
- Hours: Open daily starting at 11:30 AM.
Parking Tip: f you’re heading straight to Enzo’s, park in the Orange Garage for the shortest walk. If you’re spending the whole day strolling Disney Springs, the Lime Garage is my go-to central spot!
Enzo’s Hideaway Tunnel Bar – Official Menu & Hours
- Heading to I-Drive soon? Don’t miss The Ultimate Guide For Things To Do At Pointe Orlando 2026 – it’s just down I-Drive and perfect to pair with a Springs night!
7. Permanent Vacation – Maitland, FL
If you love hidden Tiki bars as much as I do, you have to check out Permanent Vacation! Tucked discreetly inside The Copper Rocket Pub in Maitland, look for the door marked “Permanent Vacation.”
The decor is out-of-this-world with glowing fish floats, bamboo walls, vintage tiki mugs, and subtle fog effects.
- Hours: Tuesday–Sunday starting at 5:00 PM.
Love that tiki life? Don’t miss my roundup of The Best Tiki Bars Around Orlando
Reserve on OpenTable – Permanent Vacation
Which Secret Spot Are You Visiting First?
Now that I’ve let you in on the best speakeasies and hidden bars in Orlando and beyond, which one are you heading to first? Are you sneaking through the phone booth at Crown Alley, or counting down the days for Suffering Bastard’s big Mills 50 debut?
Let me know in the comments below! Thanks for reading, and cheers! 🥂
I love Disney Springs. So I will be checking out Enzos Hideaway the next time I’m there. Thanks for a great write up!