Stay Classy This Winter With a Spiced Pear Tom Collins
Your mecca for beachside drinks and people-watching: The phrase "sipping a fruity drink on the beach in Miami," the very definition of what you'd rather be doing at any given moment, comes to life at the Clevelander. Here you'll sit outside at an Art Deco pool bar and sip frozen drinks like the legendary Miami Vice (a daiquiri/piña colada swirl) while scantily clad women with expensive chests often perform on stage and ESPN Radio hosts broadcast in the background. It's ground zero for anything spring break in South Beach, and if the rager on the ground floor gets to be too much, the C-Level bar on the roof has some of the best drinking views of the ocean.
A legendary jazz club, revived and reinvented: Once, this Little Havana legend played host to musicians with names like Holiday, Armstrong, and Dorsey and put on after-hours concerts in the era when African-American performers couldn't be in Miami Beach after midnight. It fell into disrepair in the decades that followed, but a few years ago was restored to its former glory, made up to look exactly as it did in photos from its 1930s heyday. Its kitchen serves an impressive menu of Cuban favorites like croquetas and ropa vieja tacos, and its bar slings craft cocktails like the trademark pastelito daiquiri. Daytime drinking here can be like a slice of Havana, and nighttime often brings cigars and karaoke on the back patio, where you can sing in a bandshell shaped like a giant pineapple.
A literal beer garden 40 stories in the sky: The new glass-and-steel Brickell City Centre isn't much of a tourist draw, unless your ideal vacation involves stops at Lululemon. But the absolute can't-miss in Miami's biggest new development is this bar atop the EAST hotel. You'll arrive from the hotel lobby via trippy elevators that recall Lite-Brites on acid. At the top you're in an Asian-inspired garden, flush with ferns and bamboo. Beyond Sugar's glass walls, the city sprawls north, south, and out to the water of Biscayne Bay and into Miami Beach to the east. The food is top-flight (try the boneless Korean hot wings) and the local beer selection will get you the view without having to shell out for $15 cocktails. No bar in Miami will give you more perspective of the land, and the crowd of dolled-up locals and hotel guests will have you striking up conversations with people from around the globe.
Get engulfed by the Miami skyline: For years, Miami was purely a beach vacationland, with a few mainland towers and shops for the locals. But in the past decade the city has grown up. Nothing announced that better than Downtown's first real rooftop bar, 13 stories in the sky. Pawn Broker might sit atop the Langford Hotel (a restored Downtown bank building) but the feel is of a neighborhood hotspot. At 13 stories high the bar sits comfortably above the street yet well below the city's real skyline; lit above you will be the likes of the Freedom Tower (in red) or the Miami Tower (a grab bag). The drinks come from the most creative cocktail team in the city. The go-to is the Giggle Water, a nod to Prohibition bathtub gin, served in a tiny ceramic bathtub, brimming with lavender foam atop Martin Miller W.S. gin, Champagne syrup, and tonic.
The best bar you'll find in an outhouse: Don't think for a second the people who run the Bodega taco stop are trying to keep this bar a secret. On weekends the line to get in can stretch all the way down 16th St. It's best described as secret-themed, where the only entrances are behind an outhouse door near the taco dining area, or another door that looks like the entrance to a walk-in freezer. The fun of discovering a two-level speakeasy behind a taco shop carries into the bar itself, where locals and tourists pack the place almost every night of the week. It's the kind of bar you hope to find when you say, "I want to go where the locals go," a spot enough off the beaten path that it weeds out the worst of the tourists, but still sexy enough to warrant a visit. And if you want to get to know people who call South Beach home, and aren't into dive bars, this is your best bet.
The top choice for a waterfront sunset: Maybe it's because we know in a few years EVERY bar in Miami will be a waterfront bar, but for right now there is an alarming lack of places to drink on the water in this city. The best among them is Monty's Sunset, a spot where you can sit in a swimming pool with a cold beer and watch the sun dip over Downtown Miami and Biscayne Bay. The food is your standard bar fare, the drinks aren't making any "best of" cocktail lists anytime soon. But for the sunset pictures that are guaranteed to make you lose friends on Instagram out of pure, unbridled jealousy, no Miami bar beats Monty's.
The beach comes indoors: The cadre of North Beach lifers who claim this place as a regular hangout are probably going to hate us for announcing it, but in Miami this is the funkiest, quirkiest, most random bar you can visit. Let's start with the floor, which is literally covered in sand and leaves you feeling like you spent the night on the beach across the street. Then there's the crowd, a combination of South Florida drifters, eccentric locals, and service-industry types that will give you your best window into the characters that make up the everyday Miami Beach. The decor defaults to colored neon, and the furniture is long on oversized wood deck chairs, like a North Florida beach town wandered in to sit a spell. Drinks here are cheap, by beach standards, and if you're sick of shelling out $7 per Bud Light further south, it's definitely worth the trip. Just don't tell anyone Thrillist sent you.
Where good decisions go to die: Part of coming to Miami is pushing your party limits to new, ill-advised realms. And nowhere will let you do that like this Downtown nightclub that NEVER CLOSES. It's part club, part strip club, where topless dancers do full revue shows on stage, and where the co-ed patrons tuck dollar bills into their G-strings. Here you'll see typically mild-mannered ladies spanking a stripper's ass while a guy you're pretty sure plays for the Detroit Lions makes it rain a couple of tables away. Because it's open all night, Miamians swap tales of going in at 4am and emerging at noon, typically a lot poorer than they started. But if you're looking for that all-night party experience that won't bother you with "closing time," this is the place to do it.
The unapologetic landmark dive: If you're not into happy hour at 8am, maybe the Deuce isn't for you. The oldest bar in South Beach is also its most storied, a smoke-filled dive that was home to the wrap party for TV's Miami Vice and has seen more celebrities than LIV and Studio 54 combined. The patrons here run the gamut: wealthy international visitors, models, down-and-out reprobates, service-industry pros. It's dirty and dingy, lit only by a handful of neon lights and a TV, which isn't always visible through the haze of cigarette smoke. But it's also a judgment-free zone, a place where everyone in South Beach is equal, and the happy hours start before most people go to work. Everything you wear to the Deuce will need to be shampooed a minimum of five times to get the cigarette smell out. But, hey, that's just the charm staying with you.
Miami's best craft cocktails, period: Over the past five years it seems like any bar with fewer than three windows and an Old Fashioned on the menu likes to call itself a speakeasy. But Miami's best craft cocktail bar feels like the real deal. Hidden in the back of the Gale Hotel, the spot is adorned with dark leather furniture, marble floors, and mahogany walls. The bartenders here concoct creative, delicious new drinks every day. And unlike in a lot of craft cocktail dens, you'll rarely wait long for a drink. The space is small, sometimes cramped, and feels like the police could bust in and kick everyone out at any time. But it's 2017, booze is legal, and the best place in Miami to see the amazing things that can be done with it is at The Regent.
Outdoor drinking in the world's best hostel bar: The Freehand hostel feels more like a Deco hotel than the typical dorm for European backpackers, largely because of this bar that sits in the center courtyard. The herbs grown in said courtyard are used to create the craft cocktails on the rotating menu, including a nightly punch bowl special that's the most efficient way to enjoy the ambience. The courtyard is a canopy of palms and banyan trees, a little oasis of green in cement-covered Miami Beach. The tranquil hostel pool sits just past the foliage, and hammocks and oversized deck chairs dot the property. It might be the most relaxing place to drink in Miami Beach that doesn't even have a glimpse of the water. And on a cool evening it's almost like sipping a rosemary-infused adult beverage on your own back porch.
The bar 17-year-old you would've killed to get into: At first glance, combining a selection of 150 whiskeys with a ride-on motorcycle arcade game might not seem like the BEST idea for a bar. But you're in Miami, the rules are different. For big-kid fun, no bar in Miami comes close to Ricky's, where a full-on video arcade with motorcycles, a Terminator shooting game, Pop-A-Shot, and other arcade classics give way to a big, spacious bar with its own music stage and beer pong table. Bartenders will also custom-mix a barrel of punch for you with a full bottle of booze, fresh fruit, and mixers to enjoy at your table while you play mini-beer pong. And on some nights a live band accompanies a karaoke contest, where actually good singers (and you, too, if you're brave enough) compete for real money to see who can sing the best. The devil-may-care menu includes funnel cakes, sweet hot chicken & waffles, and buckets of popcorn.
The last great locals waterfront bar: In the height of the cocaine cowboys era, Coconut Grove thrived on the sorts of swanky nightclubs that specialized in soaking up coke money. Today the Grove is known more for its fine dining than any sort of nightlife. Yet one great bar remains: Monty's. For waterfront drinking in Miami proper, it's still the king. The happy hour here draws a fantastic cross section of Coral Gables corporate types and University of Miami students, all there to enjoy cheap beer with spacious views of Biscayne Bay. During less-crowded times, it's your best mainland bet for relaxing and seaside drinking, with a fantastic selection of fresh seafood to boot.
The place to drink among young artists: Wynwood has become the "it" draw for Miami over the past half-decade, full of legitimately fantastic new spots -- but none better than Wood. Not only because it serves tacos out of an old Mercury hearse in the back (though that's a draw), but because the picnic tables and diverse crowd are the best way to experience the Wynwood scene without veering into tourist traps. Yes, the bartenders can skew towards the surly, and if you're offended by hipsters, it's not the bar for you. But it sits right at the intersection of NW 25th St and NW 2nd Ave -- the heart of Wynwood -- and people-/art-watching here is a wonderful way to spend an afternoon.