Orlando arrived a little late to the speakeasy party.
We’re a few decades removed from the 1920s when the Prohibition era forced many establishments to keep their existence secret.
The word “speakeasy” originated in England and Ireland in the 19th century when illegal drinking establishments needed secrecy. Hence, customers were asked to speak quietly while inside to avoid detection.
You can say it out loud these days, and most importantly, wine and dine without legal consequences. And yes, some passwords are still required at certain locations and there are even hard-to-find entrances at sone locations. Still, Orlando has a very welcoming vibe for anyone wishing to indulge in a unique cocktail experience.
“I think what makes a speakeasy cocktail bar a speakeasy cocktail bar is a hidden entrance or a password or a lack of signage, something like that,” said Rene Nguyen, owner of Hanson’s Shoe Repair in downtown Orlando. “Because it dates back to the speakeasies that existed during the Prohibition era.”
Orlando didn’t catch on until The Courtesy opened in 2012. It is considered the oldest dedicated craft cocktail bar in Central Florida. The line gets blurry between craft cocktail bars and speakeasies, which has a more secretive feel.
Orlando magazine has included a mix of both, including some themed speakeasies that put a bit more pop in the entertainment and theater value.
Our primary goal is to highlight some of the best places to get a great drink in Central Florida (and one cool outlier) if you’re in the mood for something more exotic than a light beer or rum and Coke.
“We have to rise to the occasion,” said Gene Zimmerman, the owner of The Courtesy. “We want to have a very distinctive touch-tone cocktail experience if cocktails are your thing.”
Once The Courtesy popped, others followed and the trend has continued over the years.
Here are some of our favorites.
1288 N. Orange Avenue, Winter Park, FL 32789 | thecourtesybar.com
At the risk of being labeled a speakeasy elitist, Gene Zimmerman isn’t big on secret knocks and passwords.
“Hate that,” he said. “I don’t want rules. I just want a drink.”
More specifically, a splendidly crafted cocktail, which is the point and purpose of The Courtesy.
Zimmerman and his wife Diana established what’s considered Orlando’s first dedicated craft cocktail bar in 2012 at a downtown location. They moved in May 2022, marking their own territory just miles away. “The tagline, our mantra, when we opened, is ‘the pleasure is ours, the Courtesy yours,’” Zimmerman said. “We want to keep that ethos of hospitality first, with quality-based, a super, super close second, and innovation.”
Try the Four Founders, a blend of scotch, barrel-aged cachaca, quinine aperitif, with pineapple and passionfruit bitters. Or a Nice Shot, gingerbread spiced rye.
“When you’re distinctive, it has this feel, like this visceral emotion that grabs you when you come in,” Zimmerman said. “The smell, the look, the personalities, all of that, it’s like, that’s where I want to go. That’s what never gets tiring for me.”
Hanson’s Shoe Repair
27 East Pine Street, Orlando, FL 32801 | 407.476.9446 | thehansonbuilding.com/hansons-shoe-repair
You need a password to get into Hanson’s Shoe Repair in downtown Orlando.
Some folks may consider this cheeky and gimmicky. And although it’s easy to connect the dots to the Prohibition era when passwords were a layer of protection from law enforcement, there is a modern-day purpose as well.
“We do change it every day,” said owner Rene Nguyen. “But the nice thing about having the password is it means every guest that comes in there is there in a purposeful manner. They chose to be there. They didn’t just stumble off the street. It’s not a foot traffic clientele.”
“What the passwords allowed us to do, along with the style of bartending that we do, the ambiance, the music, everything that we’ve carefully curated over the last ten years, what it’s allowed us to do is curate this clientele base that’s just awesome.”
Established in 2013, Hanson’s is one of the original speakeasies in Orlando. The name comes from the previous business that occupied the space, “Hanson Shoe Repair Shop,” when Andrew Hanson acquired it in 1894. The building dates back to 1884, and it is thought to be the oldest building still standing in downtown Orlando.
It’s now a two-tiered cocktail bar experience. There is a bar downstairs called Bauhaus and a stairway that leads to Hanson’s, which requires a password. Customers can call to get the daily password.
It’s a tight fit wherever you end up. The capacity upstairs is 35, including the upstairs patio. Sitting options include two two-tops and a sewing table.
But of course, the main draw is the cocktails, and Hanson’s has an excellent selection of concoctions created by Nguyen. It’s been his baby since day one.
“For me personally and what we do at Hanson’s, we don’t really focus on competitors,” Nguyen said. “We just do our thing. We don’t look at it as a competition. We’ve always felt like we have our ethos of what we think our bar should be, and we just stick to that. It’s served us pretty well.”
Mathers Social Gathering
30 S. Magnolia Avenue, Orlando, FL 32801 | 407.745.1185 | mathersorlando.com
The most challenging task when visiting Mathers isn’t deciding which vintage cocktail to order. You’ll need to get in first. No password, but suffice it to say it may be a challenge finding how to get inside once you step outside the elevator and onto the third floor. The guy sitting down at the typewriter may or may not give you a clue.
Once you’re in, you’ll want to stay. Mathers hits all the checkmarks for a fabulous speakeasy: Great drinks (all made with fresh ingredients); Ambiance and; A historic building that is easy on the eyes. Mathers even features a burlesque show every Tuesday and Saturday night.
Mathers offers an immersive experience. With certain exceptions. No TVs.
“We try to provide an atmosphere that helps remind people to stay in the moment,” said Devin Abreu, one of the managing partners and bar manager. “Our music levels are designed to be able to be loud enough where we can hear each other but low enough that our neighbor can’t hear us.”
It’s easy to ignore the sounds when there are so many sights. A swinging velvet loveseat is an inviting photo op for lovers and others with plenty of sharable appetizers. If you have a sweet tooth, you can check out some vintage candy in a turn-of-the-century-style general store tucked into a corner.
Leather couches. Oriental rugs. Stylish, dark wood and exposed brick reflect a style from the building’s origins. Formerly a furniture store and a post office, it also survived a fire in 1884 that destroyed neighboring establishments.
The 4,500-square-foot space had lived in its incarnated form since 2017, when brothers Keith, Romi, and Daniel Mawardi bought the building and brought along Abreu for his craft cocktail expertise to design the menu.
“It’s a beautiful harmony of things because these guys don’t know (bleep) about drinks,” Abreu said jokingly.
Business is good. The brothers are expanding locations to include Tampa and Jacksonville. But the original remains the standard.
“It’s for locals and people who travel to experience a vintage local bar,” Abreu said. “Because you’re drinking in a museum. This is a part of history.”
414 Flagler Avenue, New Smyrna Beach, FL 32169 | 386.402.8861 | flaglertavern.com
The Bounty has a distinct ambiance: Comfy, cozy, and approachable.
It’s why we included it as our favorite outlier.
The Bounty is tucked away among a cluster of beach bars along Flagler Avenue in New Smyrna Beach, on a second-floor perch above Flagler Tavern. On Sundays, the downstairs people come for the party, the music, and the football. The people upstairs come for the crafted cocktails and the intimate experience.
“I’ve been here at one o’clock in the morning, and I’ve seen grandparents mingling with kids that are just turning 21, and they’re talking about, ‘What’s your favorite spirit? Do you want to have a cigar with me?’” said Kristin Chmielewski, the Bounty’s general manager. “It’s just a really interesting space that brings people together.”
An interesting space indeed. Built in 1928 as a single-family home, the upstairs area has morphed into the only speakeasy in this little beach town. It’s a small space indoors, limited to 30 people. However, an add-on deck brings the capacity to 100.
But inside is where the speakeasy vibe is—all the wood from floor to ceiling is reclaimed from the original building. There’s a functioning lifeboat hanging upside down from the ceiling, a church pew, and a fireplace that was the picturesque centerpiece of a wedding reception a few months back.
Of course, we would be remiss if we didn’t mention the drinks. During the holidays, there was a seasonal blend of cocktails, including the Island of Misfit Cookies. The regular drink menu includes the King Richard (named for a loyal customer) and a one ounce pour that costs $500. The Bounty has its own Buffalo Trace barrel.
While open during the day, the action is at night: “All the lights go down. Everything up here glows red. We put on super chill, like low-fi prohibition era, the ’20s, hip-beat music.”
One last thing: Look for the staircase on the first floor. The Bounty has no signage, which is part of the mystique.
“It’s elusive,” Chmielewski said. “We’re like the unicorn.”
1817 N. Orange Avenue, Orlando, FL 32804 | 407.618.0434 | bandboxorlando.com
The BANDBOX is an acquired taste. A speakeasy that serves non-alcoholic drinks is comparable to a hamburger joint that only sells veggie burgers.
But it works. Splendidly.
Owner Kevin Zepf has created an inviting and intimate space off Orange Avenue in Ivanhoe Village on the outskirts of downtown. Step in, and you’re a time traveler. You are in the 1920s, surrounded by period pieces, photographs, and memorabilia, including hats and books. You can even buy some memorabilia, which includes scented candles in a cocktail glass. There’s even a piano and photo booth to capture the moment.
It’s a cozy place with a tight fit. Capacity is 10, which includes a staff of two or three, depending on the night. Do the math, and you may have the place to yourselves on a double date (reservations are highly recommended).
The ambiance is perfect. All you need now is a cocktail. You can order the High Hat, a whiskey maple smoked old fashioned ($10), or Trouble in Paradise, a tequila passion fruit margarita ($8), or maybe a Thomson and Scott Noughty, a Rosé/Chardonnay ($7 a glass, $27 for the bottle).
Some drinks are fully zero-proofed; some wines have 0.5 percent or less of alcohol. There are also CBD beverages on the menu.
It all adds up to the vision that Zepf created in June 2022 when he opened the place.
“It’s the opposite of what Prohibition was, but in a place where you can have an intimate drink or lounge setting that you can’t get anywhere else right now other than a coffee shop,” he said.
You may even get a chance to see character-themed performers on certain nights, including Zepf, dressed in a tuxedo. You are welcome to dress up as well in period attire.
“We have a lot of people that maybe dress up when they come in wearing Gatsby attire,” Zepf said. “We encourage that. We don’t do a dress code here per se, but we do encourage folks to come in, dress it up a little bit, so they feel as good as the place around them.”
“It’s very chic and fabulous.”
Otto’s High Dive
2304 E. Robinson Street, Orlando, FL 32803 | 321.231.7902 | ottoshd.com
Otto’s is the proverbial new kid in town, having opened in December 2022. But fair warning: They come to play.
It’s not your classic speakeasy. We’re talking about a crafted cocktail experience (there are 32 to choose from), great food, and a unique concept.
The vision for opening Otto’s is inspired by the grandfather of one of the business partners, Giovanni Fernandez. His grandfather used to own a bar during the 1940s-’50s in Manzanillo, Cuba. The other business partners—Justin Levaughn, Elise Sabatino, Sean Pagan, and Chris Munro—tried to recreate that vibe.
“Everything pays homage to the space,” Levaughn said. “It’s a piece of history.”
Come on down to the Milk District and have a look.
Those 32 drinks include the Cuban standard, the mojito, a rum drink that is refreshingly cool during the hot summer months. But crafted cocktails are all about innovation, which is why you will find the guava pastelito on the bar menu. Inspired by a Cuban dessert, the drink gets its uptick with a Plantation Isle of Fiji rum and Creme De Noyaux.
“These are all originals, not just the classics,” said Levaughn, a bartender by heart who has worked at The Courtesy and The Ritz Carlton. “Of course, we make the best mojito you’ve ever had.”
There’s also a mix of classic Cuban music in the air to complete the dining and drinking experience.
Customers have walked away impressed.
“From the moment I walked inside, I was in love with the vibe here,” said Demi A. in a Yelp review. “It’s a Cuban-inspired bar with a lovely mid-century touch. I’m coming back to try their coffee without a doubt. Wonderful first-time experience.”
Sunroom & The Guesthouse
Sunroom: 1315 N Mills Avenue, Orlando, FL 32803 | 407.630.6574
The Guesthouse: 1321 N Mills Avenue, Orlando, FL 32803 | 407.630.6574 | sunroomcocktails.com
Kristian Sirani has been around the cocktail beverage/restaurant block several times. He opened the BarBQBar in 1998. Took over the Sapphire Supper Club and turned it into the Social and launched Sky60 and EyeSpy in historic downtown Orlando.
Those visions have morphed into one: Located on Mills Avenue, the block brings a two-for-one experience since the Sunroom is tucked next to its sister bar, the Guesthouse.
“The idea was simple—a bar where everyone and anyone felt welcome,” he wrote on the Guesthouse website. “Affordable drinks in a fun environment.”
Sirani wears a number of hats at the Sunroom: Bartender, Beverage Director and General Manager.
His concoctions include “The Garden Gloves,” which combines smoky mezcal, bitter chartreuse, and a peppery Ancho Reyes liqueur with citrus juice and sweetener.
The place was bustling on a recent Friday night, mostly filled with 20-and 30-somethings getting their weekend started properly. Customers there list the martini and old-fashioned among their favorites.
“They have the best drinks and scenic atmosphere, and it pulls everybody in,” said Tom Frazier of Orlando, who was there on a date night.
Fair warning: They limit parking along the back, so you may need to opt for street parking along Mills Avenue.
At The Sunroom, they offer private rentals and the mood lighting at night creates a romantic vibe.
“Sunroom is the kind of bar you want to brag about but also want to keep a secret because it’s just so good!” Ashley S wrote in a Yelp review. “We love to make a date night out of it. Their drinks are so delicious that I pick a random drink and know I’m going to enjoy it.”
Cocktails and Screams
39 West Pine Street, Orlando, FL 32801 | 407.904.0124 | cocktailsandscreams.com
Boo-hoo. This should come as no shocker.
Cocktails & Screams is Orlando’s only Halloween-themed bar. “Stop In For A Spell, And Stay For The Boo’s,” it says on the website.
Established in 2018, the space offers various experiences for guests, including Sunday brunch and The Craft Speakeasy, both requiring reservations.
As you would expect, the drinks have a scary and spooky appeal. You can order “Franks Stein,” “Uncle Fester,” and “Horny Devil.” And if you’re hungry, the brunch menu offers “The Dexter Morgan,” an homage to a TV serial killer. You can wash that down with “The Leather Face.”
Fans of the horror genre have come away impressed.
“Cocktails and Screams is probably the best bar in downtown Orlando,” said Molly Lowman, a frequent customer. “Amazing music and fun for many age groups. Fun Halloween/satanic theme. Photo ops are everywhere! And I love the music—90s grunge, Red Hot Chili Peppers, Evanescence.”
“Do not miss your opportunity to go to this place!” JoAnn E. wrote in a Yelp review last November. “The most amazing atmosphere, delectable food, and ingenious drinks! The bar director deserves a round of applause. He gave us a personal tour, made our drinks himself, and introduced us to the owners. I felt like family.”
Plan to give up a few extra digits if you want a more intimate experience. A booking in the Addams Family VIP room entitles you and your guests (for a party between 6 and 10) access for the evening. The total price of $666 includes a $333 bar tab. Gratuity is not included.
Just remember, the vibe is horror, with a shot of comedy.
“Whatever experience you have, don’t take it to heart,” a warlock says in the promotional video for the speakeasy. “Or we may have to rip it from your pretty little chest.”
You’ve been warned!
68 E. Pine Street, Orlando FL, 32801 | 407.883.4694
The Treehouse lives up to speakeasy traditions.
You will need to look for the green door with the T-shaped handle to get into The Treehouse in downtown Orlando. Shhh. Don’t tell anyone but your closest friends.
Just go up the green stairs and step inside. You will be immersed in a complete craft cocktail experience along with an excellent selection of craft beers. You might want to sit down and savor a drink in the signature large bathtub with the “Get Naked” neon sign in the background.
The Treehouse, which opened in December 2014, has a tight but cozy feel. Dimly lit, intimate space, and a great place to bring a small group of friends. The demographics run to the younger side, in the 20-something to the 30-something range.
Thumbs up from locals, and those just passing by.
“I have been coming to Treehouse for about two years, and it feels like home,” Evan S. wrote in a Yelp review. “This is my ‘go-to’ bar in downtown Orlando. The bartenders are amazing and personable, and the staff are also friendly. I would recommend this establishment to anyone and everyone who is looking for a fun night on the town!”
Hence, why management calls The Treehouse “Orlando’s coziest cocktail bar.”
6400 Carrier Drive, Orlando, FL 32819 | 321.444.5306 | jewelorlando.com
Jewel is a super-sized speakeasy.
Located in the Pirates Dinner Adventure complex that includes Teatro Martini, Jewel offers a unique soundtrack to go along with the cocktails: Dueling pianists encompassing a variety of musical genres; Singers (including “Ms. Wiggle Waters”) belting out classic and contemporary songs; and audience participation when song requests are made.
“We had such a blast here!” wrote Ondrea in a Trip Advisor review. “I rarely write reviews, but this place deserves it! I thoroughly enjoyed the Teatro Martini show & planned to leave afterward. However, after walking thru the Jewel to exit, the dueling pianos got my attention.
“Those guys were hilarious! It’s a much better comedy act than the actual show! They did fun singalongs & interacted with the entire crowd, drawing everyone in. They inserted their own very comical lyrics to popular songs. Best date night in forever.”
But if you’re thirsty, Jewel has you covered as well. Its drink menu includes the House Classic Sidecar, and one of the Signature Cocktails, the Singapore Sling.
“This is my favorite place in Orlando to experience Dueling Pianos,” wrote Jason S. in a Yelp review. “The speakeasy vibe makes it such a more fun environment than the touristy clubs. The piano players were absolutely amazing and extremely personable. This is such a hidden gem, and I highly recommend Jewel.”
Jewel also offers a Roulette, Blackjack or Craps table for charity gaming, with the proceeds going to rotating charities. Guests can trade in their winnings for prizes.
Jewel is open Thursday through Saturday, 6:30 p.m. to midnight. The dueling pianos start at 8:30 p.m. and reservations are strongly recommended.