The Best Bars In Orlando, Florida

There are few bars in Orlando as respected as Will’s Pub. A dive and live music venue where the most obscure indie bands play for a packed house, this Mills Avenue mainstay is an Orlando landmark. The beer – craft, canned, and otherwise – is always cheap, even more so during happy hour. Add in free street parking and games of pool, and Will’s Pub won’t wreck your wallet. If ever there was a real Orlando bar, Will’s fits the bill.

If it’s a proper pint over a game of darts you’re looking for, then head for the Union Jack door on East Robinson Street. The Bull & Bush has yet to disappoint a barfly since 1987. This stalwart of the Milk District has a weekly darts league, pub quizzes, and stand-up nights, although you won’t be side-eyed if you only pop in for a quick pint of the black stuff. With Scotch eggs and shepherd’s pie on the menu (and smoking permitted, by the way) you may find yourself hanging out at this English pub well past your bedtime.

If you’re standing on the corner of Orange and Pine, you’ll be tempted to follow the sexy club-hoppers down the steps to Tanqueray’s. Submit to that temptation. This basement bar has live jazz, blues, and funk every night, adding up to an intimate underground date night that never fails to impress. With no cover charge, and decently priced – as well as decently poured – cocktails, a night here is upbeat, upscale, and cheaper than other clubs on the block.

In the eponymous Hourglass District that was named for the nearby lake, Hourglass Brewing salutes the Central Florida craft beer scene. The original Hourglass taproom in Longwood – and evil twin adjacent Sourglass Brewing – now runneth over into the southeast end of the city. You’ll find familiar tastes of Central Florida in different taps, such as the local java in the Foxtail Double Coffee Stout and orange blossom honey in 2 Million Bees And Some Hops. Only here for the beer? You bet.

Comic books. Craft beer. Cosplaying musicians. This LGBTQ friendly speakeasy in the rear of A Comic Shop is one cool nerd bar. Come for afternoons of gaming or nostalgic shows, and nights of karaoke and trivia. Whether you’ve got a pocketful of quarters for the arcade cabinets, or you plan to admire the comic book-covered bar while debating whether Brian Michael Bendis or Chris Claremont had a better run with the X-Men – you’ll make instant friends in the fandom.

A combination of dumb luck and drunken wandering will land you at the Thirsty Topher. Humbly hanging out between Ivanhoe Village and Mills 50 on “Barley Row” – this is a solid weekday destination for a curated selection of limited-case wines. There are also 24 taps of beer without stuffy pretension or high prices. A place without TV, wifi, or needless distractions, the Thirsty Topher is a chilled spot to hit for a drink with friends, amongst a crowd of beer-loving locals.

Downtown dives are plentiful, but the dapper bartenders here go the extra mile to stir sophistication into your nightcap. Below exposed wooden beams and antique chandeliers sit ladies and gentlemen as polished as the refined decor. There’s a speakeasy vibe that you’ll taste with every sip of your smoked cocktail or bathtub gin, keeping everyone squiffy yet subdued, tapping toes to live music as they await another intoxicating burlesque show.

The largest rooftop bar in O-town is Latitudes, a fabulous watering hole surrounded by tall buildings and resplendent in sybaritic beachy decor. You’ll spend the night wondering if you’re at a hip Brooklyn bar or on some slice of Caribbean paradise. Latitudes manages to be simultaneously lively and intimate, and feels like an escape from downtown, even though it’s just round the corner from the boozy debauchery spilling onto Orange Avenue.

Not one, not two, but a staggering seven bars together create the sobriety-stymying Wall Street Plaza. The carnival-like Sideshow, the intimate Hen House, and the balconies of the Monkey Bar will keep you tilted – but it’s Wall Street Cantina, the plaza’s O.G. bar, that has to be on this list. The $12 Three Amigos – one cerveza, one margarita, one tequila shot – will speed you to the downtown O-town state of mind, as Wall Street Plaza rocks on, the epicenter of inebriation.

Hanging out below the string lights of the Grape and the Grain’s patio, you’ll feel like you’re sipping wine in your friend’s backyard. That is, if your friend has a rotating schedule of food trucks, live local music, and a fantastic selection of wine, beer, and frozen boozy drinks. Graze on a meat and cheese board, and sprawl in your patio chair as the vino works its magic in your veins. When hunger pangs strike, try tacos at Black Rooster and pulled pork at Pig Floyds, round the corner.