MY Media/Courtesy of The Lobo Plantation
Nicholas Fonseca
October 24, 2014

Unlike many cities, Sydney doesn’t lean on its past in an outward way. That’s not to say that history doesn’t matter here: a quick stroll around the Rocks precinct dispels any notion of that, and the century-old pubs that dot the city’s landscape remain a draw for locals and visitors alike. But in recent years, many of Sydney’s bar proprietors have taken a cue from the drinking histories of countries and cities around the globe, outfitting their venues to mimic everything from the rum bars of vintage Cuba to dive bars of a long-gone New York City. Their ingenuity has resulted in a clutch of watering holes with character and a nod to the (not-so-distant) past, that offer food and drink menus reflecting the taste of bygone times. When you tire of tourist traps and nightly beach walks have left you thirsty for a creative cocktail, head to one of these popular destinations.

Brooklyn Social

This self-proclaimed dive bar is actually a pretty nice place to grab a cold beer. A new addition to Sydney’s ever-changing food and drinks scene, it’s meant to ape beloved NYC haunts of old (think CBGB or Max’s Kansas City) and the drink list certainly pays tribute to their reputations—it boasts 44 different types of gin alone. The American diner-style food menu is nothing special, though it’s full of items that will coat your stomach well if you’re planning on a big night—try the mac-‘n’-cheese balls, onion rings, fried chicken, or (paging Homer Simpson!) the doughnuts.

The Lobo Plantation

Still never been to Cuba? No matter: this well-hidden basement bar does a fine job of recreating life in the Pearl of the Antilles. Rum is the specialty here: they’ve got more than 150 bottles of the drop sourced from around the world. Order a stiff drink and have it served with panache by stylish bartenders in bowties and braces. 

Easy Tiger

The waitresses here wear hot pants and zoom around on roller skates, and the whole place looks like a basement rec room that hasn’t been touched since 1978. Each table is given a walkie-talkie to order old-school dishes like fondue or chicken Kiev. Bring friends and a good attitude, and splay out in a corner as The Doobie Brothers and Donna Summer blare from the sound system.

Earl’s Juke Joint

This converted butcher shop is meant to pay homage to the raucous watering holes that dot the alleys of New Orleans, but really, it’s just a great place to hang out. Cocktails are prepared in a snap, or you could boldly order the Fernet-Branca, a cult Italian liqueur they keep on tap. It’s famously said to taste like licorice-flavored Listerine. Don’t say I didn’t warn you.  

Frankie’s Pizza

Frankie’s brings an appealingly scuzzy vibe to downtown Sydney, where corporate types roam by day and (until recently) not a whole lot seemed to be happening at night. The front room looks like an Italian restaurant from a bygone era when clams casino were still on the menu, but walk to the back, and you’re in a proper dive bar, where you can order drinks and slices while Guns ‘n Roses blares from the speakers (or a live band rocks the nearby stage).

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