The Password
Twitter Check Required
"You have to call the phone number on their Twitter profile to get the daily password. Then you knock on a nondescript door and whisper it to the doorman. It sets a fun, conspiratorial tone for the date immediately."
💡 Date Tip
The interior is tiny, but the rooftop patio is the real gem. It’s enclosed by brick walls and ivy, feeling private yet open to the stars.
Hanson's Shoe Repair.
Located in one of the oldest buildings in Orlando (1883). It was an actual shoe repair shop that served as a front for a speakeasy during Prohibition. The history is real.
Bartender's Choice
Don't order a vodka soda here. Tell the bartender your preferred flavor profile (e.g., "smoky and sweet"), and let them create art.
Otto's High Dive. 🍹
A neighborhood rum bar that earned a Michelin Bib Gourmand. It’s gorgeous—whitewashed brick, velvet booths, and tropical plants. It feels like 1950s Havana.
Date Tip
The food is as good as the drinks. Order the "Cuban Frita" burger to share. It’s elevated comfort food that keeps the vibe relaxed but impressive.
Rum Library
"They treat rum with the respect usually reserved for whiskey. If your date is adventurous, ask for a flight. The staff are incredibly knowledgeable and unpretentious."
Maximum Tiki
Maitland
"This isn't cheesy party-city tiki; it's immersive art. Smoke machines, custom mugs, and decor that took years to collect. It transports you to another world instantly."
💡 Date Tip
Be careful with the "Zombie" limit (usually 2 per person). These drinks are notoriously strong. It's a fun challenge to navigate together.
Permanent Vacation.
Hidden inside the Copper Rocket pub, you have to find the specific door to enter. Once inside, the lighting is low, the music is exotic, and reality fades away.
The Garnish Game
The drinks come with elaborate garnishes—fire, flowers, bananas carved into dolphins. It’s pure theater and guarantees fun photos.
Tanqueray's. 🎷
Located in the basement of an old bank. No cell service, no windows, just live funk, jazz, and soul music every single night. It’s where the local musicians go after their gigs.
Date Tip
Go late. The band usually starts firing on all cylinders around 11 PM. It’s the perfect place to dance close when you aren't ready for the night to end.
The Descent
"Walking down the steep stairs off Orange Avenue feels like entering a secret club in New Orleans or New York. It’s gritty, real, and arguably the most authentic bar in downtown."
18th Floor
Downtown View
"Orlando is flat, which makes this height majestic. You can see the entire city grid, the distant theme park fireworks, and the sunset reflecting off the glass towers. It feels cosmopolitan."
💡 Date Tip
Arrive 45 minutes before sunset to snag a spot on the balcony railing. The transition from golden hour to city lights is the show.
AC Sky Bar.
A sleek, modern rooftop experience. It’s all glass, concrete, and wind. The cocktail menu relies heavily on gin and refreshing botanicals, matching the breezy altitude.
The Cloud
Try their signature smoked cocktails. They arrive under a glass dome filled with aromatic smoke—a little drama for the table.
The Imperial. 🛋️
By day, it's Washburn Imports, selling exotic furniture from Bali and India. By night, they dim the lights, open a wine bar, and let you drink while sitting on the inventory.
Date Tip
The Ivanhoe Village location has a hidden back patio known as "The garden." It feels like a private courtyard in New Orleans.
Imported Mood
"The lighting comes from hundreds of unique hanging lamps and chandeliers for sale. It creates a warm, cluttered, incredibly cozy atmosphere that makes everyone look good."
Wash & Fold
The Entrance
"Walk into the tiny, fully functional laundromat. Pick up the payphone on the wall. A secret door disguised as a washing machine swings open to reveal a neon-soaked Havana courtyard."
💡 Date Tip
It transitions into a dance vibe late at night with live Latin music or DJs. Go early (8 PM) for conversation, late (11 PM) for dancing.
Dirty Laundry.
It’s cheeky, fun, and doesn't take itself too seriously. The cocktail menu plays on the theme with drinks like the "Spin Cycle."
The Patio
The "inside" is actually an open-air courtyard covered by a canopy, so it feels breezy and tropical even in the summer heat.