If you only visit one Sydney haunt, consider Maybe Sammy in the city’s historic Rocks district, ranked No. 29 on last year’s World’s 50 Best Bars list. The place, which evokes the Rat Pack-era glamor of the 1950s, currently boasts a Stardust menu of 12 signature blends for around A$25 each. The gin-based My Fair Lady is presented with a large bubble on top, which bursts into scented vapor, while the Elizabeth Taylor-inspired National Velvet is a smooth vodka and sake concoction.

What the venue lacks in size, it makes up for in pure alcoholic punch. This standing-only ode to mezcal in the city center, ranked 41st on the World’s 50 Best Bars list, often has a line, but it’s certainly worth waiting on. The Margarita OK! packs a punch, with tequila, mezcal, lime and orange oil (A$22). Or try the La Petit Mort, which is made with a hefty dose of mezcal that’s distilled with a raw turkey breast, served with rambutans.

Styled after classic Italian enoteche, the cozy, walk-in-only wine bar Paski is a recent addition to Oxford Street. Browse the illuminated industrial shelves, which house about 450 varieties from small producers. There’s no paper menu: Everything from food to booze is on the frequently changing chalkboard. Among the more unusual wines are the orange-hued Terragno from Italy (A$19 a glass) or, from closer to home, the Australian Poco Rosso, a highly drinkable chilled red.

A sophisticated vibe complete with leather booths and marble tables sets the scene at Dean & Nancy. Although the place boasts sweeping city views, the Around the World cocktail menu takes drinkers far beyond Sydney. The Giza (A$27), presented in a smoking wine decanter reminiscent of the peaks of Egypt’s famous pyramids, is a surprising espresso martini twist, combining raspberry and hibiscus burnt honey with filter coffee. The also impressive bar food menu has plates designed for sharing.

A stone’s throw from the famed Enmore Theatre in the city’s Inner West area is Bar Planet, a psychedelic French-influenced martini bar. Martinis are customized: Grab a paper menu and circle your preferred spirit, preferred dose of vermouth and whether it’ll be an olive or a twist. If that sounds like too much work, order the dirty martini or the Chateau (both A$21), essentially a chamomile vodka-laced lemon meringue pie in a glass.

Only a curtained doorway separates La Salut from the 100-year-old neighborhood watering hole the Norfolk pub, but this Inner West tapas bar transports guests to Barcelona. The wine list is a book-long tour through Spain, so lean on the very knowledgeable and friendly staff. The Lectores Vini Pomagrana, a light, chilled red from Conca de Barbera made from Trepat grapes (A$16), is a refreshing drop for a balmy evening.

Bar Conte specializes in one thing: the Negroni. On a quiet corner of Riley Street, the place is lined with Italian posters for a buzzy vibe that refrains from veering into kitsch. Open the menu for a brief history lesson on the bitter Italian aperitif’s origins, then eyeball the many variations on offer, featuring rare vermouth and a deep selection of gin. Stick to the classic: The Conte’s Barrel-aged Negroni (A$30) uses Antica Formula vermouth; for something lighter, the sbagliato.

The Bearded Tit, a self-described “local clubhouse for the parched, hungry and curious,” isn’t for the easily offended, but it offers a good time in the city’s Inner West suburb of Redfern. Grab a booth inside among the taxidermied birds and gilded mirrors and browse the extensive drinks list for a local craft beer or wine. The cocktail list includes the dry but fruity Pash Rash, with Stolen Golden rum and the passion fruit liqueur Passoa, which packs a punch at an affordable A$18.

Spread across the top two levels at Hotel Palisade in the Rocks, Henry Deane’s bright rooftop is the perfect perch for sunset views of Sydney’s skyline and harbor. The John Lemon, made with vodka, lemon sorbet, curacao and lemon myrtle (A$20), is lovely tipple when the humidity is rising. For more of a kick, the Coffee Culture is a caffeinated take on the Negroni.

Fans of this cozy Champagne and cocktail bar range from the after-work crowds to pretheater sets. Down a winding central business district lane, the bar’s petite tables and plush seating are suited to small groups looking for French-inspired small plates—think duck terrine, charcuterie, oysters, frites—and strong drinks in a mellow atmosphere. Cocktails nod to both 1920s Paris and modern classics like the Gin Gin Mule (A$25), a freshing antidote to the summer heat.

Dear Sainte Eloise has a wall-size wine selection and tables spilling into the alley, making it ideal for people watching and local pet owners. On a wine list nearly as long as the George Orwell memoir it references (Down and Out in Paris and London) are gems like a Giacomo Boveri Timorossa white or South African Viognier (around A$17 each). Bewildered by choice? The “mystery glass” is free if you can name the grape and region.

Whether you’re coming from the beach or the city, book before heading to this wine bar wedged among Paddington’s high-end fashion boutiques. The small tables make it easy to nudge knees with a date, and the menu has soul and swagger. Don’t miss the house special of smoky fish roe bottarga that comes with a soft, warm pretzel. Freshly made strozzapreti puttanesca is punched up with capers and olives (A$35). To counter the salt, try a glass of Il Vei Malvasia, a rustic Italian wine.