Away from its famous harbor and bland city center, Sydney has a thriving inner-city scene where the flavor is distinctly hip and homegrown. Here,

By Brian Johnston
Photography by Chris Chen

A little vignette of Sydney life, take time out to sit in a café in the heart of the Surry Hills district. An espresso machine hisses and gurgles and white cups rattle on saucers. Watch the barista work his or her magic with the machine: a delightful ballet of steam and metal levers. The burned-sugar fragrance of coffee hangs in the air, and locals rustle newspapers and munch on muffins.

Then walk down a sun-dappled street lined with eucalyptus trees. You might pass a cinnamon-scented ice-cream parlor where colorful ziggurats of gelato tempt passersby. Farther on, you’ll find chic restaurants with snappy white table linen, where you can nibble on Sydney rock oysters with a squeeze of lime as you admire a passing parade of punks, office workers, tottering fashionistas, wannabe artists, and disheveled journalists from the newspaper offices down the road.

This is the new Sydney, laid-back and eclectic, sometimes pretentious, usually stylish, and, most of all, much more interesting than ever before. Gone are the days when Sydney relied solely on exploiting its magnificent harbor setting and beaches to lure locals outdoors and visitors to its shores. Now, one of the world’s most beautiful cities and renowned party capitals is all grown up, looking to a more layered experience, and acquiring an increasingly adult sophistication in its dining, shopping, and nightlife scenes.

“I think we’ve got the balance right in Sydney: we work hard, but then we also like to enjoy ourselves,” Sydney bar czar Justin Hemmes comments. He points out that inner-city Sydney now has the vibe of parts of New York or London—but with beautiful beaches only a 10-minute drive away. “It’s about living as well, and lifestyle. Sydney has everything.”

Away from Sydney Harbour, the inner-city suburbs of Surry Hills, Darlinghurst, and Paddington, clustered between the central business district and expansive Centennial Park, are where it’s all happening. They seem unlikely candidates for a revival. Surry Hills, once the hub of the local rag trade, was where poor immigrant workers huddled in slum conditions and razor gangs roamed the streets—a gritty, desperate environment perfectly captured in Ruth Park’s best-selling The Harp in the South trilogy. Darlinghurst and Paddington were similarly depressed working-class precincts until gays and other trendy professionals started to move in during the 1980s. By the ’90s, back alleys were sprouting sleek homeware shops and inventive little restaurants, and the shocking price of real estate was the conversation du jour among the chattering classes.

But while this inner-city transformation has been two decades in the making, it is these suburbs’ current capacity for constant updating that makes them eternally new. The area is a microcosm of Australian food and fashion trends: see what’s next, what’s hip, what’s already “so yesterday.” If you haven’t been in the last couple of years—heck, if you haven’t visited this year—you’ll find plenty of novelty and, thankfully, some old favorites. You’ll also find that Surry Hills, Darlinghurst, and Paddington have each emerged with their own distinctive village feel and urban vibe that, away from touristy Darling Harbour and Circular Quay, offer the best taste of contemporary Sydney life to any visitor who cares to join the locals.

SURRY HILLS
Sydneysiders are obsessed with the new, and sometimes in Surry Hills it seems that the notorious 15 minutes of fame has been whittled down to five. It’s remarkable, therefore, that some of the area’s early trendsetters are still around. Eleven-year-old Longrain (85 Commonwealth St.; 61-2/9280-2888) was one of the first stylish restaurants to open in this rough-edged area, and still pulls in the crowds with its legendary caramelized pork hock with chili ginger and five-spice. Similarly, Red Lantern (545 Crown St., 61-2/9698-4355) is now a Surry Hills institution where cookbook author and TV chef Luke Nguyen creates Vietnamese-inspired goat curry and shallow-fried snapper with fish sauce. Farther along Crown Street at Billy Kwong (No. 355; 61-2/9332-3300), another TV personality, Kylie Kwong, has served up mod-Chinese cuisine for the last decade and still seems to be flavor of the month.

In a suburb packed with such celebrity chefs, any new eatery really has to rise to the challenge. Opened two years ago, the revamped Beresford Hotel (354 Bourke St.; 61-2/9357-1111)—once a dyed-in-the-wool gay pub with blacked-out windows and testosterone on tap—was one of the first entries in the latest phase of Surry Hills’ renewal. It lays claim to being a 1920s New York– style beer garden and trattoria, though one wonders whether squid-ink tortellini with crabmeat was on the menu back then. Never mind: the bar is Art Deco–ish and the quality of chef Danny Russo’s cooking is top notch.

Another new kid on the block, Toko (490 Crown St.; 61-2/ 9357-6100), clearly takes its inspiration from neighborhood stalwart Longrain, aiming to do for Japanese cuisine what the latter did for Thai, using the same warehouse-style setting and communal tables. Sydney’s obsession with sushi rolls is thankfully on hold here; patrons munch on soft-shell crab with wasabi mayonnaise or slices of duck breast with nashi pear. Toko’s success is shared by its sultry next-door extension, Tokonoma, a shochu bar and lounge where shimmering glass and flowing wood create an effortlessly stylish space. The beautiful interiors are matched by equally beautiful food, as well as some of the best drinks in town.

Bentley Bar (320 Crown St.; 61-2/9332-2344), which opened to rave reviews in 2006, has just emerged from a head-to-toe makeover—a sure sign of how quickly tastes change in Surry Hills. The once funky pub space is now a more sophisticated restaurant setting in black and gold, with red leather benches and solid wood tables. The Spanish- and French-influenced menu pushes the boundaries into the post-molecular world; chef Brent Savage describes it as “progressive.” Try the salt cod with mussels and smoked potato mousse, or rolled duck breast with enoki mushrooms and cuttlefish, and leave room for the honeycomb chocolate bar for dessert. It’s all so delicious, you can forgive the self-conscious cleverness.

Surry Hills dining is nothing if not varied; another favorite of the moment is Bistrode (478 Bourke St.; 61-2/9380-7333), which dishes up no-nonsense but top-quality British-inspired meals such as steak in red wine sauce and Wagyu corned beef with mustard. Then there’s that particularly Sydney pastime, the weekend breakfast, with the Bourke Street Bakery (633 Bourke St.; 61-2/9699-1011) attracting long queues for its oven-fresh sourdough and pastries. It’s quite the place to be seen, proving once again that informality doesn’t preclude pretension in Sydney.

If you’re just after a drink, the Winery by Gazebo (285a Crown St.; 61-2/9331-0833) pushes all the trendy buttons. It has an eco-conscious wall of ferns and grass-topped bar, a variety of global nibbles (chorizo sausage rolls; mussels with lemongrass), and—a surprisingly recent fad in sunny Sydney—an outdoor space in the form of a large courtyard with wonderful city views. Relax: the sommelier won’t sniff at your wine choice here and, in winter, the mulled wine with brandy is a welcome treat.

For a more esoteric drinking experience, the new Absinthe Salon (87 Albion St.; 61-2/9211-6632) serves the aniseed-flavored spirit the traditional way, with ice water dripped over a sugar cube. Owners Gaye Valttila and Joop van Heusden are more than happy to bend your ear at length about the drink’s mystical properties. There are 18 varieties to choose from (nothing else is served), but select wisely, because three drinks is the maximum—no one wants patrons turning into a green fairy like Kylie Minogue in Moulin Rouge! Absinthe novices should try the velvety Swiss brand Kübler and easy-on-the-palate Jade Nouvelle-Orléans.

Surry Hills is really a diner’s destination, but a spot of shopping wouldn’t go amiss. Wheels & Dollbaby (259 Crown St.; 61-2/ 9361-3286) helped pioneer the fashion scene here. Featuring glamorous rock- and punk-inspired looks, the label has covered the backs of The Rolling Stones and Pink, among others; most recently, Katy Perry stopped by for some threads for her Australian concerts. Textiles and homewares are also worth seeking out. Bird Textiles Emporium (380 Cleveland St.; 61-2/8399-0230) specializes in hand-printed, organic fabrics; Spence & Lyda (16 Foster St.; 61-2/9212-6747) features everything from furnishings and lighting to glassware and accessories from designers such as Europa and Missoni; Chee Soon & Fitzgerald (387 Crown St.; 61-2/9360-1031) stocks decorative arts and irresistible knickknacks; and David Met Nicole (382 Cleveland St.; 61-2/9698-7416) is stuffed with vintage bric-a-brac sourced from around the globe. The newly opened Flight 001 (285 Crown St.; 61-2/9332-1777), aimed squarely at the trendsetting jet set, has an interior as smooth and streamlined as an aircraft’s, giving a sleek edge to all things retro.

DARLINGHURST
There was a time when Darlinghurst (“Darlo” to its mates) was all about Oxford Street, and Oxford Street, just blocks from the red-light district of Kings Cross, was all about the gay scene. Now, the neighborhood attracts everybody, from nightclubbers of all persuasions to students, young professionals, and anyone with an interest in art-house cinemas and good bookstores.

Not surprisingly, Darlo bars are eclectic: drop in for a rum among the tropical fish at Rambutan; relax on a chaise longue with a cocktail in the inimitable Victoria Room; or have a beer surrounded by fluorescent furniture at the Green Park Hotel.
The unlikely hit of the moment is Doctor Pong (1a Burton St.; 61-2/9332-3565). With its dartboards and ping-pong table, the bar might remind you of your grungy university days, yet it also manages a surprisingly cool vibe.

Arguably the best bar to open in Sydney in a decade, Shady Pines Saloon (Shop 5, 256 Crown St.; no telephone) may sound like an Arizona brothel, and yes, it does go in for the country-and-western theme. Expect stuffed wildlife (the cow’s head near the bathroom is positively frightening), cigar-store Indians, and old-time photos in sepia. Scotch and bourbon are the drinks of choice, but there is also a good selection of beers and cocktails, including an excellent mint julep that will have you feeling like Scarlett O’Hara in no time. The quality of the drinks is just one of the attractions; the friendly bartenders, mellow vibe, and cheerful crowd are enough to make you overlook all that kitsch.

Another new place that excels at producing good vibrations with an American twist—this time vaguely New Orleans—is Eau-de-Vie (229 Darlinghurst Rd.; 61-2/9357-2470). With its impressive array of boutique beers and spirits, the bar attracts a cool crowd who kick back to the sounds of funk and jazz. The bar staff is excellent, in keeping with owner Sven Almenning’s mission to serve top-quality drinks. “No one leaves Tetsuya’s gushing about the decor,” he says, referring to Sydney’s internationally renowned Japanese restaurant. “Yet when it comes to bars, most owners spend their cash on making the place look great rather than focusing on fantastic drinks.”

You’ll find Eau-de-Vie at the back of Kirketon Hotel (61-2/9332 2011; 8hotels.com; doubles from US$240), one of a better class of boutique accommodations now catering to this district’s increasingly chic clientele. Housed in a renovated 1930s building, the interior sets a hip and stylish tone—think lots of moody browns offset by striking Scandinavian chairs—without ever feeling contrived.

When it comes to eating, Darlo’s Victoria and Oxford streets are the place to go for anything from Balkan seafood to Cambodian noodles. The food scene isn’t as dynamic as in Surry Hills, relying instead on familiar standards for the pre-nightclub crowd. But Universal Restaurant (Republic 2 Courtyard, Palmer St.; 61-2/9331-0709) bucks the trend, sitting in the courtyard of one of the latest hip apartment blocks in a riot of color. Here, chef Christine Manfield keeps the palate guessing with the use of eclectic flavors that range from jasmine tea to five-spice, wasabi, blood orange, and green mango. Try the duck and ginger-pickled cherries, or veal sweetbreads with aged feta and hazelnuts. Few chefs have such a knack for marrying disparate flavors into such a satisfying whole.

PADDINGTON
Oxford Street—which stretches for four kilometers from the corner of Hyde Park in the CBD all the way to Bondi Junction—is the artery that links Surry Hills, Darlinghurst, and Paddington. As you leave Darlinghurst, Oxford Street’s hustle and bustle momentarily falters as it passes sandstone army barracks. It picks up again as Paddington announces itself with a distinctive Victorian-era town hall. The suburb is full of sedate colonial remnants, not least in its rows of terrace houses with wrought-iron balconies and gleaming brass door knockers, home to arty professionals with an eye to location. Vast Centennial Park is on the doorstep, and Coogee Beach and city center are both a short drive away.

The long-running Paddington Markets (paddingtonmarkets.com), held every Saturday in the grounds of the local church, are an enduring part of the scene and, indeed, have helped to cement Paddington’s reputation as the fashion hub of Sydney. Young artists and designers sell their creations here and some, such as Lisa Ho, Paablo Nevada, and Dinosaur Designs, have gone on to greater things. Dozens of other well-known Aussie designers have their shops in Paddington, from Alannah Hill, Charlie Brown, Leona Edmiston, and Sass & Bide to swimwear specialist Tigerlily.

This year saw the debut of a flagship store from New Zealander Kate Sylvester (168 Oxford St.; 61-2/9380-4244), which currently brings out the summer feel in crisp cottons and bold evening colors alongside Sylvester’s younger, more irreverent range. Australian fashion label Jac + Jack (39 William St.; 61-2/ 9380-6011) has also just opened its first dedicated store. Designers Jac Hunt and Lisa Dempsey made their name with quality knitwear, but have moved into other natural fibers such as cashmere, silk, and cotton. Their new shop is on William Street, now edging out Oxford Street as the true fashion guru’s destination.

With their scattered boutiques and art galleries, the leafy backstreets of Paddington are well worth a wander, and you might eventually come out at Five Ways where, at the junction of five streets, locals linger over weekend coffee before browsing through patisseries, upmarket bottle shops, and delicatessens. In the evening, neighborhood pubs like the Grand National (161 Underwood St.; 61-2/9363-4557) offer enticements of their own. Mind you, you’ll want to return to the Oxford Street strip to visit the new Wine Library (18 Oxford St.; 61-2/ 9328-1600), a sexy little bar that allows you to taste the latest cult wines in a retro setting, accompanied by mod-Mediterranean food from an open kitchen.

For proof that old is new and that fad can turn anything to fashion, make your way down to the Paddington Bowls Club (2 Quarry St.; 61-2/9363-1150) on a weekend. Not so long ago, lawn bowls, though a great Australian institution, was derided as an exceedingly dull pastime for suburban retirees dressed in all-white gear. But Paddo Bowls was one of the first such clubs in Australia to introduce barefoot bowling, in which non-members could turn up in their civvies and enjoy an afternoon of beer and flirting. Before long, the shoeless sport had become a local sensation.

Perhaps you have to be Australian to appreciate how the “daggy” (unfashionable) can be so exceedingly daggy that it’s actually cool again. But when you’re done with all those nightclubs and bars and are needing a change of pace, barefoot bowling awaits. With the smell of eucalyptus in the air and the grass between your toes, surrounded by bright young things in their summer cottons, you could hardly have a more authentic Sydney experience.