My favorite childhood photograph is from the early seventies, from one of my family's annual pilgrimages "up north" from Melbourne. In the picture, my mother, my three sisters, and I are fanned out on the steps of the Sydney Opera House; its famous flares, which had been finished just a year earlier, seemed to billow in the wind. We are all smiling and looking out toward the water. It isn't easy to sum up an iconic city in a brief, sentimental snapshot, but to me, the image crystallizes my feelings about Australia's premier city. The enthusiasm I see in my young face in that photo is the same feeling I get every time I come back—Sydney is a place of reinvention, one that promises endless possibilities. Sydney is about breaking the rules.
Whether it's the annual Gay and Lesbian Mardi Gras, which began here in 1978 as a protest movement and paved the way for gay rights throughout Australia, or the 2000 Summer Olympics, a watershed event that firmly placed the city in the global arena, Sydney residents are increasingly demonstrating an intense national pride. No more apologies for geographical isolation, goes their new mantra. Sydneysiders no longer look overseas for inspiration; more and more, they are finding it in Sydney itself, distilling the best parts of their city's internationalism without discarding its unique cultural quirks. (Exhibit A: Office workers wear flip-flops to work.)
One essential attribute that Sydney's neighborhoods once lacked was—how to put this delicately?—culture. Renowned as Australia's sun, sand, and sex capital, the city has spent the past five years quietly evolving into a more sophisticated, more thoughtful version of its former self, and the districts to bookmark are no longer the ones you'd expect. Don't worry, the bronzed-surfers-on-Main-Street phenomenon is still alive and well. But the non-beach-related suburbs are finally getting their due: ex-industrial areas, the inner west, and the docklands are all coming into their own as essential destinations. The arts scene is lively, and theaters are full (especially when well-loved Aussies like Cate Blanchett or Geoffrey Rush—both alumni of Sydney's Belvoir Street Theatre—are performing). Social and environmental changes are on the agenda, thanks to the city's newly minted lord mayor, Clover Moore, a fiftysomething independent known as much for her progressive platform as for her flamboyant personal style (spiked black hair, dark red lipstick, dog collars). Since taking office last April, she has made a commitment to enhancing "Sydney as a City of Villages" and celebrating the uniqueness of each of its disparate enclaves.
Sydneysiders are reveling in the knowledge that they live in the culture-and-style capital of the New World. As their town grows and flourishes—the population, now 4.2 million and counting, has risen by 11 percent since 1998, thanks to a decade-long real estate boom and an influx of young professionals—the sun shines ever brighteron this most laid-back of international cities. As for tomorrow...to borrow a favorite phrase from Nicole Kidman, one of the city's best-loved daughters: Bring it on.
Surry Hills and Waterloo
Author Ruth Park set her best-selling novels The Harp in the South and Poor Man's Orange in a gritty, Depression-torn Sydney. The fictional Darcy family lived in Surry Hills, a Dantean inner-city hell where razor gangs roamed the streets. But the neighborhood's bad old days are well and truly behind it: instead of a seedy bar on every corner, there is a buzzy new café, and real estate prices are the hottest topic in the bars and restaurants that line Crown Street. Meanwhile, nearby Waterloo, once an industrial no-man's-land, has emerged as one of Sydney's best rags-to-riches stories. The action takes place along a short stretch called Danks Street (a misnomer, these days), where boutiques cater to every craving—aesthetic and culinary.
Young locals, priced out of ritzier areas like Woollahra and Double Bay, have turned Surry Hills into a thriving urban village, and the restaurant revolution here marches apace. Red Lantern (545 Crown St.; 61-2/9698-4355; dinner for two $54), a converted terrace house painted a provocative shade of scarlet, serves updated versions of Vietnamese classics. The shallow-fried whole snapper with fish sauce, lime, and ginger and the roll-your-own rice-flour crêpes are local favorites. • A few doors down is Café Mint (579 Crown St.; 61-2/9319-0848; lunch for two $23), a storefront dishing up well-priced food with a North African spin. Order the delicately fragrant breakfast couscous spiked with cinnamon and honey, or the meze plate for two, and let the charming waitstaff talk you into a second caffè latte—they make the best in town. • Old-time bistro favorite Tabou (527 Crown St.; 61-2/9319-5682; dinner for two $93) has the Rive Gauche ambience down: menu scrawled on a gilded mirror, bentwood chairs, bloody steaks, perfect pommes frites, and double-cooked soufflés. • Celebrity chef Kylie Kwong, who has a popular cooking show down under, is still packing them in at her minuscule hot spot Billy Kwong (355 Crown St., Shop 3; 61-2/9332-3300; dinner for two $85), where she serves up dishes (crispy-skinned duck with blood orange sauce) inspired by her Chinese family's recipes. • The late art-world enfant terrible Brett Whiteley called Surry Hills home in the eighties, and his studio (once a T-shirt factory) is now an "art museum," the Brett Whiteley Studio (2 Raper St.; 61-2/9225-1881). There's an exhibition space downstairs, while the upstairs has been preserved as it was when Whiteley lived there, complete with memorabilia, postcards, photographs, and artwork. Whiteley did achieve a certain notoriety during his lifetime (he struggled with heroin addiction), but only since his death have his haunting, light-infused paintings been fetching jaw-dropping prices at auction. • The Pacific, an antipodean answer to New York's Soho House (both bear the stamp of designer Ilse Crawford), is slated to open in the old Railway Institute building on Elizabeth Street—next to Central Station—this summer. • Forget the forbidding public-housing blocks towering behind you and settle in for an espresso at the Danks Street Depot (1-2 Danks St.; 61-2/9698-2201; lunch for two $27), part of a collective of galleries called 2 Danks Street, in Waterloo. This contemporary art complex includes established local dealers such as Utopia Art Sydney, Brenda May Gallery, Stella Downer Fine Art, and Gallery Barry Keldoulis. • Around the corner, Country Trader (197 Young St.; 61-2/9698-4661) specializes in 17th- to 20th-century French antiques. The vast showroom is overflowing with Louis XVI furniture and massive chandeliers displayed in a hushed, rarefied atmosphere. • Waterloo's pièce de résistance is Fratelli Fresh (7 Danks St.; 61-1300/552-119), a grocery store-provedore set in a converted warehouse. The merchants bring a comforting, Italian-inspired sensibility to their array of gourmet goods: stacks of imported canned tomatoes, dozens of olive oils, crinkly brown paper bags or boxes in place of plastic bags. There is also a dazzling selection of cheeses, produce (always impeccably displayed), herbs, imported butters, pasta, and hard-to-find items like tiny fresh figs, truffle oil, and Italian sodas. A new café, Sopra (61-2/9699-3174; lunch for two $28)—Italian for "above"—recently opened; weekends see hipsters and the stroller set alike jostling politely for position to get their Eurofix.
Tamarama, Clovelly, and Coogee
If Bondi is seared into the consciousness of travelers to Sydney, that's because it is one of the world's most beautiful urban beaches. Insiders know, however, that there is a whole waterfront world just beyond these well-trod sands. Although the main hub of eating, drinking, and socializing is still Bondi's north-south boulevard, Campbell Parade, there is a less flashyscene to be had in Tamarama, Clovelly, and Coogee. Slightly off the backpacker radar—for now—these suburbs, where folks do their shopping in sarongs and raise sun-kissed children in relative peace and quiet, radiate unpretentious cool.
Tamarama, sometimes dubbed Glamarama for its disproportionate quotient of Sydney's re- nowned Beautiful People, like model-turned- swimwear designer Jodhi Packer, is a small, sheltered bay tucked between Bondi and Bronte beaches. The glamour here is just as high-voltage as at Bondi, but the pristine strand is far less crowded. Bronte, with its rolling lawns and buff lifeguards, is more of a family-oriented destination and offers plenty of post-beach refreshment, most notably at Sejuiced at Bronte Beach (487 Bronte Rd.; 61-2/9386-9538), where swimmers go for a quick smoothie. • A memorable experience for those unfazed by vertiginous heights and large crowds is the Bondi to Bronte Walk, an easy stroll along the cliffs running between the two beaches. • Barzura Café (62 Carr St., Coogee; 61-2/9665-5546; dinner for two $54) is a local favorite for its ocean view and Mod-Oz food, such as whitebait fritters and smoked-trout risotto with crisp leeks. For Sunday brunch, a spicy duo of nasi goreng (Indonesian fried rice) and a Bloody Mary will cure any hangover.• Seafood aficionados flock to A Fish Called Coogee (229 Coogee Bay Rd.; 61-2/9664-7700; dinner for two $31), a nouveau fish-and-chips shop by the beach, serving everything from barbecued shrimp to marinated barramundi. (Fish-and-chips, along with cricket, is one of the few British institutions Australians continue to embrace.) • After dark, it's off to Cushion (242 Arden St.; 61-2/9315-9130), a bar-café on the ground floor of the Crowne Plaza hotel. Given its killer beach views, you can forgive some decorating faux pas. • On rough-surf days, locals head to Wylie's Baths (Neptune St., Coogee; 61-2/9665-2838), for laps and (you guessed it) spectacular views of nearby Wedding Cake Island, a rocky outcrop popular with scuba divers. • Fashion mavens make a beeline for the Frock Exchange (221 Clovelly Rd., Clovelly; 61-2/9664-9188), a boutique run by Belinda Seper, who has an eye for fashion's Next Big Thing. Here, shoppers can sell their designer clothes for either cash or B Dollars, which can be used in any of Seper's stores.
Circular Quay and the Central Business District
No matter how jaded Sydneysiders get, few can resist boasting about their harbor. Just try suggesting to a Sydney resident that there might be a finer curve of water, a more arresting opera house, or a grander bridge somewhere in the world and watch him bristle. Not so long ago, the streets around Circular Quay ground to a halt once the office workers went home. But since the 2000 games, some of Sydney's finest restaurants and bars are within a heartbeat of the harbor. The hulking series of warehouses that make up the Overseas Passenger Terminal building (West Circular Quay) is still the disembarkation point for cruise ships, but also houses several glamorous dining destinations, all of them taking natural advantage of their waterside status. (Insider tip: When planning a romantic dinner for two, avoid nights when cruise ships are in, unless you want to be staring down a row of portholes all night.)
If Bellinis and mai tais are your speed, Cruise Lounge (Overseas Passenger Terminal, Level 3; 61-2/9251-1188), a postmodern study in chocolate brown and slick detailing, with black-clad staff to match, is cocktail heaven. Floor-to-ceiling windows and a sun-drenched terrace mean uninterrupted views of harbor traffic: everything from ornate tall ships to zippy water taxis. • The newly minted Ocean Room (Overseas Passenger Terminal, ground level; 61-2/8273-1277; dinner for two $132) features an up-close-and-personal marine experience: the restau- rant's focal point is a 20-foot-high glass wall of fish tanks. • From the Ocean Room it's a quick walk to the eastern promenade, for a ringside seat at Guillaume at Bennelong (Circular Quay; 61-2/9241-1999; dinner for two $139), tucked into the southern shell of the Opera House. French-born chef Guillaume Brahimi's ravioli of Clarence River prawns with a veal jus-and-foie gras emulsion are a revelation. • After a performance, a cocktail at the Opera Bar (Sydney Opera House, Lower Concourse; 61-2/9247-1666) is essential. The futuristic, low-ceilinged space is beneath the concourse; pull up a stool at the curved, backlit bar or, following a matinee, nab an outside table to take advantage of afternoon sea breezes. • In summer, old-timers and first-date couples alike gather at the Open-Air Cinema (Mrs. Macquaries Point, Royal Botanic Gardens; 61-2/9231-8111), which screens mainly art-house films. The setting—beside the Botanic Gardens and overlooking the harbor—is thrilling even for repeat visitors. Many go just to watch the screen rise magically from the water at the beginning of the show. • Don't pass up the Vintage Clothing Shop (147-49 Castlereagh St., Shop 5, CBD; 61-2/9267-7155), a tiny gem that every Sydney stylist has on speed dial. Besides gowns, coats, and shoes, it also stocks jewelry, hats, gloves, and accessories, not to mention the occasional big-name-designer haul—Givenchy, Dior, Hermès—from a private collection. • The restaurant everyone is talking about doesn't have a beachside address. Instead, it's hidden in a basement (albeit with swanky neighbors like Chanel and Paspaley Pearls). All the better, really, because that way there's no distraction from the perfectly prepared Greek-but-not-as-you-know-it dishes at Omega (161 King St., CBD; 61-2/9223-0242; dinner for two $124). This is refined Greek food for the 21st century, served in a sleek, dramatic space with molded-plastic chairs and Florence Broadhurst wallpaper. The drama plays out on the plate as well: chef-owner Peter Conistis produces such praiseworthy house specialties as anchovy baklava and his twist on the classic moussaka—made with seared scallops, eggplant, and taramasalata.
Sydney's wild inner west is a chaotic maze of crowded streets and smoky bars (at least in those places where the anti-smoking laws have yet to be applied), where every other person is pierced or has a menacing dog in tow. Don't be afraid, though—it's for show. Newtown is a great promenading neighborhood, with all the hallmarks of a college town (the University of Sydney has a campus nearby), including miles of cafés, music venues, and vintage furniture stores. The area has long been a stronghold of the city's gay and lesbian community, but in a more low-key way than flamboyant Darlinghurst. Weekends are the best time to visit.
The 1,600-seat Enmore Theatre (130 Enmore Rd.; 61-2/9550-3666), housed in a legendary Art Deco building, has seen its fair share of boldfaced names; patrons who were lucky enough to snag tickets are still raving about the intimate gig the Rolling Stones played here on their 2003 tour. Other recent headliners: Alicia Keys and Chris Isaak. • The equally cherished Bank Hotel (324 King St.; 61-2/9565-1730), one of many traditional pubs in the area, serves authentic Thai food in its beer garden. • The Peasants Feast (121A King St.; 61-2/9516-5998; dinner for two $62) is devoted almost entirely to food that is delicious and virtuous. Try the organic pork belly with eggplant caviar, or the slow-roasted free-range duck with spiced red cabbage and grilled apple. • Furniture hunting is a popular sport in these parts, particularly along the King Street strip. Newtown Old Wares (439 King St.; 61-2/9519-6705) is packed with mid-century finds, such as arc lamps and kidney-shaped coffee tables. • If blowing the dust off old treasures isn't your thing, take a detour to Prettydog (1A Brown St.; 61-2/9519-7839). This eclectic fashion boutique used to specialize in vintage clothing but has since evolved into a showcase for up-and-coming local designers, as well as more established names like Karen Walker and Nicola Finetti.
THE DRESS CIRCLE
There are few better ways for a dedicated retailaholic to spend a Saturday than browsing the stretch of Oxford Street from South Dowling Street to tony Queen Street. But the path less traveled (at least by those not wearing Manolos) is just off this busy thoroughfare. William Street, with its tiny footpaths and Victorian shop fronts, has a distinctly European flavor, and patrons dress the part in Prada and Jimmy Choos. While these narrow streets are a magnet for young style devotees who know their Burberry from their Balenciaga, the area is also popular with the pearls-and-twinset contingent, breezing in from moneyed Woollahra, just streets away. Deeper into the heart of Paddington, the shopping and café precinct Five Ways is made for stylish loitering; Sydney's literati and media whiz kids have made this crossroads their own.
In one of the city's best fashion melting pots, the silk slips and hand-embellished gowns at Collette Dinnigan (33 William St.; 61-2/9360-6691) share a postal code with the work of big-name, cutting-edge Belgian designers—such as Dries Van Noten, Veronique Branquinho, and Walter Van Beirondonck—at Poepke (47 William St.; 61-2/9380-7611). • Andrew McDonald Shoemakers (58 William St.; 61-2/9358-6793) creates bespoke footwear popular with fashionable brides and men looking for one-of-a-kind loafers or classic brogues. • Just William Chocolates (4 William St.; 61-2/9331-5468) is a third-generation family business that has won the hearts and stomachs of Sydneysiders. The exquisite handmade chocolates could put an end to any diet, although the svelte young things that populate this stretch give the impression that they abstain. • Belinda Menswear (29 William St.; 61-2/9380-8873) is the newest addition to the street, and the youngest in Belinda Seper's Sydney empire. Her first menswear store stocks Helmut Lang, Marni, Yohji Yamamoto, Martin Margiela, and Rick Owens. • Down the hill, Leona Edmiston (88 William St.; 61-2/9331-7033), Australia's answer to Diane von Furstenberg, specializes in flattering day dresses, mainly in jersey and silk.
The madding crowds tend to thin out a little as you move away from Oxford Street, giving you a real feel for the neighborhood. Squint and you might mistake Five Ways, the convergence of five streets some three blocks northwest of William, for a particularly sunny Parisian arrondissement. Gracious Victorian terraces give way to a small but perfectly formed shopping precinct with glittering glimpsesof the water (listen for the occasional foghorn, issued from far out at sea). • Here you'll find a French pâtisserie, La Gerbe d'Or (255 Glenmore Rd.; 61-2/9331-1070), that rolls out wickedly buttery croissants; a traditional pub, the Royal Hotel (237 Glenmore Rd.; 61-2/9331-2604); and Parlour X (213 Glenmore Rd.; 61-2/9331-0999), a fashion-forward boutique stocking labels like Vivienne Westwood and Cacharel. There are also several cafés, a day spa—the Paddington Beauty Room (217 Glenmore Rd.; 61-2/9356-8700), known for its addictive La Prairie facials—and a fine wineshop, Five Way Cellars (4 Heeley St.; 61-2/9360-4242), that carries many hard-to-find vintages. • Come Saturday, the Paddington Markets (395 Oxford St.; 61-2/9331-2923; www.paddingtonmarkets.com.au; Saturdays 10-5) roll into town. A sprawling clothing, jewelry, and craft showcase that takes over the grounds of the Paddington UnitingChurch, this is where you'll spot burgeoning talents in design and art, so snap up their creations while they're still at bargain prices. Many of Australia's best fashion labels—Zimmermann, Third Millennium, Bracewell, Paablo Nevada, and Lisa Ho—got their start here.
Sydney's many wharves are experiencing a rebirth. The Finger Wharf at Woolloomooloo paved the way in the late nineties and its star-studded trattoria, Otto (6 Cowper Wharf Rd.; 61-2/9368-7488; dinner for two $100), still sizzles. • W Hotel (6 Cowper Wharf Rd.; 61-2/9331-9000; doubles from $415) generates its own models-and-movie-stars ecosystem. Russell Crowe owns a penthouse next door. • One of Sydney's liveliest converted pubs, the Tilbury Hotel (12-18 Nicholson St., Woolloomooloo; 61-2/9368-1955), is packed on weekends. • Revelers sate post-cocktail hunger with a mushy peas, mash, and tomato sauce pie from Harry's Café de Wheels (Cowper Wharf Rd.; 61-2/9357-3074), a kitschy wharf institution. • The Jones Bay Wharf has blossomed with Flying Fish (Pier 21, 19-21 Pirrama Rd.; 61-2/9518-6677; dinner for two $108), a dramatic loft space where the menu takes inspiration from France and the sub- continent. • The Sydney Theatre Company (Pier 4/5, Hickson Rd.; 61-2/9250-1777) has opened a new space near the restored landing at Walsh Bay, a 20-minute walk from Circular Quay.
Some of the city's best Opera House views are from this sleek, low-slung hotel in the Rocks district (beside Circular Quay). DOUBLES FROM $387. 7 HICKSON RD.; 800/233-1234 OR 61-2/9241-1234; sydney.park.hyatt.com
Smoothly run harborside tower with an excellent spa and around-the-clock gym. DOUBLES FROM $344. 199 GEORGE ST.; 800/332-3442 OR 61-2/9238-0000; www.fourseasons.com
One of Sydney's most design-heavy hotels, with 30 suites and a lovely rooftop garden. DOUBLES FROM $172. 18 SPRINGFIELD AVE.; 61-2/9358-1533; www.regentscourt.com.au
A residential-style property that caters to privacy-seekers. Don't miss the pool's fiber-optic constellation ceiling. DOUBLES FROM $566. 89-113 KENT ST.; 800/223-6800 OR 61-2/9256-2222; www.observatoryhotel.com.au
Sophisticated travelers feel right at home at this 33-room hotel with a nightclub and an award-winning restaurant. DOUBLES FROM $258. 5 BRIDGE LANE; 61-2/9240-3100; www.establishmenthotel.com
BEST VALUE A hip boutique outpost near Paddington's great shopping. DOUBLES FROM $152. 114 DARLINGHURST RD.; 61-2/9360-6868; www.lotel.com.au