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It's the ideal Sydney afternoon, so hot and drowsy that the huge city center green space of Centennial Park is especially inviting. Families sit at picnic tables, pouring rose from metal jugs while their dogs loll motionlessly in the sun. In one corner an ad hoc cafe marked by a picket fence has sprung up. Men in deck shoes and slouchy shorts sit on the grass, beers in hand, laughing as a lamb on a spit catches fire; a chef rushes to tamp down the flames. Skinny girls in sunglasses and stilettos flirt with a staffer who wheels a barrow full of beer through the crowd—it's a sop to the long lines at the bar, set up haphazardly on hay bales. This is the Park, a hip spot run by the city's hottest restaurateurs, aiming to re-create the casual charm of an outback wedding breakfast—hence the straw, spit roast and all-inclusive approach. It's a scene that perfectly sums up Sydney now: welcoming, outdoorsy, effortlessly stylish, warm (in every sense) and just a little off-kilter.
Sydney's raffish allure is the result of a ten-year transformation, one that began with its much-praised staging of the Olympics in 2000. "That's when Sydney lifted its skirt and danced," says Ben Macpherson, the rangy and handsome brother of supermodel Elle. "Sydney used to cringe about being Australian. Everyone wanted to get out of here. But there's a sense of pride now." The country's economic resilience in the past few years has served to buttress that buoyant mood: Thanks to Australia's vast natural resources, commodity exporting has made it virtually recession-proof. The slowdown elsewhere never materialized here; indeed, out of politeness, many locals change the subject when conversation drifts toward the global financial crisis.
One area has benefited above all from the financial boom: arts and culture, long also-rans in this egalitarian, sporty city. "After so many years of beating itself up about being the good-looking airhead city, Sydney is embracing its inner thoughtfulness now," notes Remo Giuffre, who runs TED's new Sydney outpost. September saw the debut of Sydney's first major art fair, Sydney Contemporary, aimed at top-tier domestic galleries and collectors, though the rule that art isn't assessed duty taxes when purchased in Australia makes it an appealing destination for international buyers, too. "Sydneysiders are engaging far more with the arts of all kinds now," says the genial and soft-spoken Barry Keldoulis, a former gallerist who's now helming that show. "What I love about Sydney is that it's forward-thinking but not prescriptive."
Four neighborhoods best sum up the energy and appeal of the city today. Two have been longtime hubs: the beaches, which define Sydneysiders' weekends (and early mornings), and nearby Paddington, undoubtedly the best place to shop in Australia. Two other areas have emerged only as the city has transformed: the surprisingly leafy inner-city suburb of Surry Hills, now home to artists and designers, and CBD (for Central Business District), where galleries and bars jostle for space among the office towers.
Sydney Harbor & Central Business District
The Opera House (Bennelong Point; sydneyoperahouse.com) is a beguiling building: It sits like an idling spaceship on the harbor's edge, white-tiled roof shimmering in the sun. The surrounding area, though, was long a disappointment in comparison, home to little more than nondescript offices and tacky tourist-aimed stores. In the last ten years, though, everything has changed. The daytime CBD is now the city's cutting-edge cultural hub, while after dark it's home to Sydney's most stylish nightlife.
By day the best place to start is the Museum of Contemporary Art Australia (140 George St., The Rocks; mca.com), which sits on an old quay directly opposite the Opera House. Last year the MCA debuted a massive $49 million expansion, a stark Rubik's Cube-like addition to the fusty old customs house in which it's long been housed. The transformation was ringmastered by director Liz Ann MacGregor, a dynamic expat Scot with a mass of curly red hair and a fondness for Vivienne Westwood. "When I announced I had taken the job, I was astounded at the prejudices I encountered about Australians—the usual jokes about cricket and koalas. People here are interested and open," she says. During her decade-plus tenure, MacGregor has cannily combined populist programming, like an Annie Leibovitz retrospective, with edgy international shows, such as 24-hour marathons of Christian Marclay's film The Clock. "Until fairly recently, any sophisticated Sydneysider would have steered well clear of the area," she says, "but the rise of pop-up shops and creative events has transformed the vibe."
Much of the funding for such one-offs has come from John Kaldor (kaldorartprojects.org.au). The textile magnate has used his vast resources to support continuous pop-up shows in the city center; typical is last year's photography-takeover installation by Thomas Demand at a hotel in modernist architect Harry Seidler's masterpiece, the MLC Center. "People ask how I choose projects, what intellectual process I use, but it's only from the gut," Kaldor says, tapping his stomach forcefully. The crowds flocking to the shows have prompted gallerists to abandon warehouse-like spaces in the inner suburbs for smaller, more convenient perches in the CBD—notably the much-admired Sally Breen (Breenspace, 17-19 Alberta St., 3rd fl.; breenspace.com), who represents this year's Venice Biennale entrant, Simryn Gill.
Public artworks now proliferate on the streets, among them the late Bert Flugelman's beloved Pyramid Tower, the Dobell Memorial Sculpture (nicknamed the Shish Kebab). The mirrored spiral was recently moved from its original site on a pedestrian mall downtown to a new location on a traffic island—an upgrade, since it now dazzlingly reflects the forest of office buildings that enclose it. Nearby is the charmingly offbeat installation Forgotten Songs, by Michael Thomas Hill. Dozens of empty iron cages have been strung up randomly like metal washing hanging on a line across a lane; trilling birdsong is piped into the street. It's easy to overlook the quiet commentary of the piece: Each chirp is the call of a native species that once populated the area before European settlers drove it away.
The CBD is transformed at dusk, as office workers hop onto buses or commuter ferries at Circular Quay. Until five years ago, Sydney had prescriptive liquor laws that precluded anything but huge, rowdy pubs—known here as hotels—from operating. The maverick local mayor, Clover Moore, was keen to expand beyond such beer-swilling sports hubs, so she championed a "small bars" bill that introduced licenses costing only $350. Essentially, Moore's move made it economically viable for an entrepreneur to open a small drinking den, many of which mushroomed in the CBD. With few residents to complain about late-night noise and ample space in the forgotten Victorian alleys that still run behind the gleaming modern shopping streets, it's become a cocktail mecca.
Dozens of chic, speakeasy-like joints dot the area, each deliberately discreet: Stitch (61 York St.; 61-2/9279-0380; stitchbar.com) lurks in a basement, specializing in aperitif-style drinks such as the Devil's Work, with rum, Montenegro and tequila. The Singer sewing machines along the bar are a nod to its name. The Rook (56-58 York St., 7th fl.; 61-2/9262-2505; therook.com.au) is tucked away on the roof of a building more fitting to dentists' offices than a Dark and Stormy; its menu is filled with witty touches, like a drink called Calligraphy, served with a white feather. The retro-styled Grasshopper (1 Temperance Ln.; 61-2/9947-9025; thegrasshopper.com.au) huddles in an alley with its door propped ajar in welcome. Starting a tab behind the bar produces a cassette tape to use to reclaim it, while cocktails are served in mismatched jars. The buzziest new spot, though, is Bulletin Place (10-14 Bulletin Pl.; bulletinplace.com), on the second floor of an office building on its namesake street. It's hard to find but not to be missed. Here the day's concoctions are custom-devised according to the barkeeps' trip to the farmers' market that morning; a four-strong drink list is then handwritten on a roll of butcher's paper fixed to the wall. (Arrive early, as they're in limited supply; though latecomers can relax—there's a conventional drinks menu, too.) Sit on a stool at the bar and ask chatty co-owner Tim Phillips for a Left Hook, a punchy blend of Calvados, maraschino and Campari.
The best place to stay in the CBD has long been the Park Hyatt (rooms, from $835; 7 Hickson Rd., The Rocks; 61-2/9256-1234; sydney.park.hyatt.com), in an unbeatable location, its huge suites equipped with balconies offering direct views across the quay to the Opera House. It's now being rivaled by the new QT (rooms, from $360; 49 Market St.; 61-2/8262-0000; qtsydney.com.au), though, a maximalist boutique hotel with an exuberant attitude. With decor like Jonathan Adler at a disco—think black lacquer, low lighting and vitrines filled with goofy objets—the after-dark atmosphere here is in tune with the newly nightlife-heavy CBD. Its best suite, though, is decidedly old-fashioned. The hotel is a conversion of a pair of landmark office buildings, whose C-level executives once sat on the tenth floor. Their former offices have been converted to suites, of which 1022 is the most lavish. Once the chairman's perch, many of its original features have been retained: a private balcony, ornately carved wooden wall panels and, fittingly for the CBD today, a vintage cocktail cabinet.
Paddinton & Woollahra
Today sisters Nicky and Simone Zimmermann are synonymous with Sydney's sexiest bathing suits. "We're not printing koalas on them," Nicky says, "but there's a certain optimism to our designs that is very Australian." When they started out 20 years ago, though, they were hustling their homemade pieces from a stall at the markets in Paddington. (A stallmate was future superstar Collette Dinnigan, "but she might not admit it," says Nicky, letting out a Champagne bubble laugh.) She considers that experience crucial. "If you're in Sydney, the first place you start up—at least if you're smart—is in Paddington." That's because the area has long been the city's most stylish enclave. It's the local answer to New York's West Village or London's Notting Hill, where independent boutiques and closet-sized restaurants jigsaw together.
Growing up in the Sydney suburbs, Nicky always yearned for Paddington (or Paddo, as locals call it—Australians are obsessive about abbreviations). "When it's spring, it's full of jasmine, bushes and bushes and bushes," she swoons, sitting at Jackies (1c Glenmore Rd.; 61-2/9380-9818; jackiescafe.com.au), a monochrome cafe that's the resident fashion world's canteen. "The scent was so powerful." Year-round, the wide, low-rise streets here are surprisingly lush, shaded by trees or overgrown bushes, whether jasmine or jacaranda, whose iridescent lilac petals carpet the sidewalks by summer.
The best way to start exploring Paddo is to take a stroll along the main drag, Oxford Street. Pause at the junction with Glenmore Road, where a handpicked cluster of smart stores has been dubbed The Intersection (theintersectionpaddington.com.au). The Zimmermanns' flagship (212-16 Glenmore Rd.; zimmermannwear.com) is now here, along with outposts for every notable Australian label, including vampy and retro Alannah Hill (118-120 Oxford St.; alannahhill.com.au) and Ksubi's (140 Oxford St.; ksubi.com) premium denim (just watch for the skateboarders who slalom unpredictably through the door, shopping bags in hand).
Retail spills over into the backstreets, too, with tiny terraces repurposed as showrooms or boutiques. Tailor Patrick Johnson (46 Liverpool St.; pjohnson.com.au) co-opted a discreet townhouse as an airy atelier; passersby may wonder why suits hang in the window. It's as much a clubhouse as an office, as clients drop in to linger—chatting, grabbing a beer from the kitchen or heading upstairs for a fitting with a casual ease that's decidedly Down Under. Though he trained in London, Johnson creates designs that are equally Australian: "a sporty way of dressing that isn't flashy," he says. He can't forget his ties to Britain, though: There's a winking shrine to Prince Charles, the man he considers the world's most stylish, in one of the fitting rooms.
Along nearby William Street, workmen's cottages now house cottage industries: showrooms, shops and restaurants. Typical is modern Italian wine bar 10 William St (10 William St.; 61-2/9360-3310; fratelliparadiso.com). Low-lit and white-tiled, it smells of olive oil and cold cuts, with a menu full of staples like veal saltimbocca or mozzarella di bufala; a cloudy, unfiltered Prosecco imported specially by the owners is a highlight on the wine list. Ben Macpherson and his wife, Belynda, picked the street for the only store for his cashmere label, Banjo & Matilda (76 William St.; banjoandmatilda.com). (He followed his older sister into the fashion business, albeit behind the scenes.) "In Sydney, if you want to buy something cool, Paddo would be the first place to go." He explains that his designs are inspired by the Australian lifestyle—for example, the ideal cashmere sweater to stuff into a beach bag and then slip on as the evening grows chilly. "There's an unselfconsciousness here," he says. "Sydney style is relaxed. We don't do prim and proper."
Perhaps the only place where that might not be true is neighboring district Woollahra. It's Paddington's older sibling: greener, wealthier and, yes, a little more subdued. Queen Street is lined with boutiques like Robert Burton ($ 25 Queen St.; robertburton shop.com), where brightly colored Bensimon sneakers are piled up like candy on tables, or Anne Schofield's antiques store (36 Queen St.; anneschofieldantiques.com), with a stash of jewelry that locals mention cravingly. Ultra-stylish moms picnic with strollers on a patch of lawn on Moncur Reserve; doubtless they provision at Victor Churchill (132 Queen St.; victorchurchill.com.au), the area's Wonka-like butcher shop. Grab the brass handles shaped like sausages on the door and duck inside for gourmet gawking: The jewel-box-like interior features butchers at work as well as case after case of homemade treats—pots of saffron-and-chorizo risotto, perhaps, or a smoked salmon, spinach and Parmesan quiche.
The Hughenden Hotel (rooms, from $140; 14 Queen St.; 61-2/9363-4863; the hughenden.com.au) is chintzy but charming, housed in two buildings that straddle the road; a portrait of Dame Edna monitors reception through the day. The eight rooms in the modern annex are fancier, but a stay in the original home is the only chance to see the hotel's resident ghost, reportedly a little girl in a blue dress who's often spotted on the stairs. Don't leave the area without trying some snow-crab sliders or a tomato salad with flaked olives at Chiswick (65 Ocean St.; 61-2/8388-8688; chiswickrestaurant.com.au), the bustling bistro run by bad-boy chef Matt Moran. Shaven-headed and swaggering, Moran wears all black while others sport kitchen whites. He stands proudly in a garden that he planted on-site to ensure access to fresh produce at all times. "This is a beautiful, leafy suburb, one of the most expensive in the country," he marvels. "Where else do you get a place like this just five minutes from the CBD? You could be in England."
Twenty years ago, a Sydneysider would've sputtered at the thought of spending time in Surry Hills. It was a slumlike and unloved inner-city suburb, with little appeal other than the signature plane trees that line almost every street. The problems were simple: Historically, Surry Hills was a grimy corner of the city, consigned to industry; far from the water, with no view of the harbor or cooling sea breezes, it was a place few of the wealthy pioneering locals would have chosen to live in.
Indeed, the Victorian row houses were built to house immigrant sweatshops for the garment industry; after manufacturing moved overseas, students commandeered the ramshackle setup as cheap housing, making Surry Hills (and Redfern, the more run-down area to its south) ground zero for grunge. Of course, those low rents soon caught the attention of creative types: designers, writers, artists. Ceramist and vintage dealer Addison Marshall is typical of the early colonizers. He bought an apartment here in the mid-1990s, just as the area began to improve. "It's always had a boho vibe. I'd never move," he says. "The shop owners still say hello to you every morning."
Now, thanks to Marshall and his ilk, Surry Hills is Sydney's hippest district, home to stores like Platform 72 (72 Oxford St., Darlinghurst; platform72.com.au): Think of it as a brick-and-mortar Etsy, where some 40 young artists rent space to sell their creations. Next door, He Made She Made (70 Oxford St., Darlinghurst; hemadeshemade.com) is helmed by two designers; their workshop is in the rear while a concept gallery showcases installations by friends and colleagues.
Expat Brit Orlando Reindorf converted a two-story house into The Standard Store (503 Crown St.; thestandardstore.com.au), one of the area's most appealing shops, with an eclectic mix of homewares like handmade Maison Balzac candles and emerging labels such as Life After Denim. Surry Hills reminds him of a London village corner: "There are terraced houses on treelined streets," he says. "You can walk to the city center, and there's football and cricket right on your doorstep." Boutique marketing and digital firms have followed Reindorf's lead, co-opting the old houses as hipper headquarters than generic buildings in the CBD. "I don't know if I'm the right director for that music video," frets one thirtysomething power-breakfasting at Bills (359 Crown St.; 61-2/9360-4762; bills.com.au), one of the best-known local cafes, famed for pillowy ricotta pancakes with honeycomb-sweetened butter.
No one in Surry Hills seems to have a single, full-time job: Bar owners resurface as artists; designers double as professional musicians. No wonder Harry Levy opened Cleveland's (311 Cleveland St., Redfern; 61-2/9698-8449; clevelandsoncleveland.com), a barber shop-cum-cafe offering what one wit dubbed a "short black and sides," or a straight-razor shave plus a snifter of espresso served in charmingly wonky cups (handmade, of course, in a home kiln by a potter who also dabbles in coffee roasting). Coffee is a tricky topic in Australia, the rare subject about which usually affable locals will bristle. The cafes have a fastidious approach to roasting and brewing, and two of the city's best roasteries are in Surry Hills. With poured concrete walls and iPad-wielding staff, Reuben Hills (61 Albion St.; reubenhills.com.au) smells of the fresh beans from the huge roasting columns upstairs. Come by on Friday at 10 a.m. for a weekly cupping session, in which exotic blends are sniffed and tasted. Once the votes are tallied, the most popular flavor becomes the espresso of the day. The window at Single Origin Roasters (60-64 Reservoir St.; singleoriginroasters.com.au) is festooned with Rube Goldberg-esque equipment. Inside, with his rockabilly tattoos and bushy beard, barista Sean McManus painstakingly explains each brewing method, such as the siphon, which bubbles like a test tube. "The full immersion offers a permanent heat source," he says before wielding the aeropress, a suction-powered plunger that produces a softer but still strong-flavored brew. "You can take one home—it's just $50."
Don't leave Surry Hills without making a pilgrimage to Dinosaur Designs (585 Elizabeth St., Strawberry Hills; dinosaurdesigns.com.au), whose jewelry and homewares are designed and handmade in a nearby factory by husband-and-wife duo Stephen Ormandy and Louise Olsen. The company's Day-Glo resin treasures can be found throughout the city, but overruns and one-offs are sold at the cheekily named Extinct, in the factory's lobby. Olsen would never consider moving the operation out of its longtime home. It's part of a creative community in Surry Hills, she notes; alongside the boutiques and barbers are galleries and studios, even museums, like the former atelier of Brett Whiteley, an intimate of Francis Bacon, which has been preserved and reopened to the public (2 Raper St.; nsw.gov.au). "There are still so many artists and studios," Olsen says. "You're more likely to see a splattered, painted pair of jeans here than anywhere else."
The Beaches: Bondi & Bronte
"It's called the Bondi Bubble—people who live in Bondi don't like to leave," says Remo Giuffre, a longtime resident. "Once the Bondi bug has bitten, it bites deep and it bites hard." Standing on the waterfront of Campbell Parade, it's easy to see why: Barely a ten-minute drive from the CBD, Bondi is one of the most glorious and inviting beaches in the world. A vast, eyelash-shaped swathe of golden sand, it sits on an east-west axis, so sunshine is guaranteed all day. Protected by a crescent bay, the ocean currents are dampened, making the waters safe for even the youngest paddler.
Early on a Sunday morning, hundreds of Sydneysiders are already ensconced. "Bondi is an amphitheater of sand," says Barry Keldoulis, director of the Sydney Contemporary art fair. "The beach here has a grandiose but human scale to it." He's right: Despite the hordes, it doesn't feel crowded but joyous and energized. Families frolic on the eastern end, quietly monitored by lifeguards in signature red-and-yellow swim caps. Solo sunbathers dot the sand, throwing down towels to loll with a book they pretend to read while stealing a nap or a furtive, forbidden cigarette. It's a beach for the buff or the bold—after all, in 1961, this is where fashion student Peter Travis introduced the skimpy Speedo swimsuit to the world (with classic Aussie wit, it was quickly nicknamed a "budgie smuggler").
Don't worry about squeezing into one after lunch at Sean's Panorama (270 Campbell Parade; 61-2/9365-4924; seanspanorama.com.au), a small restaurant overlooking the beach that's among Sydney's most beloved gourmet treats. It's unfussy; every table has a bunch of garden roses in a jar, and servers rattle off the daily menu, which is scratched on chalkboards. But chef-owner Sean Moran is renowned for the freshness of his food; he grows all his own fruit and vegetables. Nearby, the stylish, honey-blond-haired crowd at the Bucket List (Bondi Pavilion, Queen Elizabeth Dr.; 61-2/9365-4122; thebucketlistbondi.com) spills out onto ocean-facing patios. It's a faux-fisherman-styled bistro, with lobster-pot lamp shades and a namesake mural of to-dos like "Party with the Queen." Pause there for a glass of wine after lunch before tackling the 40-minute Bondi-Bronte cliff walk.
Thanks to their waterfront location, Sydney's eastern suburbs are the city's toniest. Each is defined by its beach, and the pleasant coastal hike provides a glimpse at two of the most notable. Before scaling the cliff, though, don't miss the swimming club at Bondi's tip, Icebergs SLC (1 Notts Ave.; icebergs.com.au). Surf Lifesaving Clubs like this are an Australian institution found on most beaches, but the Art Deco Icebergs complex is among the country's most iconic. An aperitif upstairs at Icebergs Dining Room and Bar (61-2/9365-9000; idrb.com) is delightful—for the last decade, the Mediterranean restaurant has been one of the city's sceniest spots—but the real draw is more prosaic: Skip an ocean dip and instead plunge into the outdoor pool. Wedged into a cliff, it's refilled with seawater whenever the waves crash.
Anyone can muster enough energy for the Bondi-Bronte cliff walk, a gently undulating path that snakes along the water's edge. Athletic types use it for jogging, stopping off to use the outdoor gym equipment dotted along its length. Indeed, only the fittest should brave the surf at the small beach Tamarama. Currents are ferocious, so it's a place to strut or lounge, which is why locals call it Glamarama. Bronte, though, is more welcoming. Quieter than Bondi and pleasantly secluded with green lawns fringing the sand, it's popular with families. A few minutes' walk up the hill leads to Bronte's parade of shops, which ends with the stylish cafe Three Blue Ducks (143 Macpherson St.; 61-2/9389-0010; threeblueducks.com). Waiters with long, bleached hair and deep tans saunter around, clearly anxious to get back on a surfboard while preppy, pop-collared parents gorge on avocado toast with crusty bread or mud crab with ginger, garlic and shallots. At one of the outdoor tables, you'll hear tropical birds cawing loudly, the only sound but for the crash of the ocean. It's jarring to reflect that Bronte is just 15 minutes from the city center—until the birds squawk louder, and it no longer matters.
If you go to Sydney, Qantas flies daily direct from Los Angeles and Dallas-Fort Worth. qantas.com.au