Three Perfect Days / Sydney

The city's 4 million or so residents are rightly proud of their world-class restaurants, museums, and galleries; they revel in the hedonistic outdoor lifestyle afforded by a temperate climate along with ample beaches and bushland. But beneath the gloss, there are hidden depths. In the cobblestone lane-ways of the historic Rocks district, in the prisoner-hewn sandstone structures that dot the streets, and even in the larrikin spirit that suffuses modern Sydney culture, the city’s colourful convict past still echoes.

DAY ONE / Awaken to the sight and sound of water lapping at the edges of the marina outside your room at BLUE (formerly the W Sydney). This hip boutique hotel opened at The Finger Wharf at Woolloomooloo following the wharf’s redevelopment. In the wharf’s cavernous interior, goods conveyors and loading platforms bear testament to the structure’s original incarnation as a wool- and cargo-handling facility from the 1900s. Despite these relics, the hotel’s rooms decked out in chocolate and cobalt blue are pure modern luxury. It can get drafty in these high-ceilinged heritage buildings, so snuggle up under a brazier in the BLUE Café down-stairs while you fortify yourself with ricotta pancakes or a tangy bircher muesli with apples and blueberries.

It’s time to get your walking boots on. With the imposing sight of naval battleships in the background, follow the boardwalk and climb the higgledy-piggledy sandstone steps toward Mrs Macquaries Road. Keep strolling until you reach the sandstone outcrop known as Mrs Macquaries Chair, and rest in the ample shade cast by a Moreton Bay fig. During times of strife in the fledgling convict settlement, the wife of one of the early governors used to retreat here, gazing over the sparkling waters in a bid to soothe her heavy heart.

You’re in tourist territory now, with the Harbour Bridge and Opera House sweeping into frame, so savour the view and press on around the headland to the Royal Botanic Gardens. Take in “Cadi Jam Ora: First Encounters,” a garden display that features the area’s Aboriginal history, or stroll through other gardens such as the rain forest walk, palm grove, or native rockery.

Don’t linger too long, as you’re heading for Taronga Zoo, about 12 minutes by ferry from nearby Circular Quay. When you arrive at the lower gates, take the Sky Safari aerial gondola to the top, and you’ll discover why real estate–obsessed Sydneysiders ruefully remark that giraffes enjoy the city’s best water views. Specialised tours led by animal keepers offer an intimate, behind-the-scenes experience. Don’t miss seeing native animals like wallabies, kangaroos, quolls, bilbies, and gliders.

You have reservations for lunch at Aria, so head back across the water and take a window seat for fine dining with a casual vibe. Enjoy house specialties by chef Matthew Moran that include sweet Bangalow pork belly crowned with the thinnest, crispiest wafer of apple.

Stroll back past the buskers plying Circular Quay to the Museum of Contemporary Art. Teetering on the brink of bankruptcy a few years ago, the museum has a new director and fresh sources of funding, including sponsors and the government, that have rejuvenated the only publicly funded venue dedicated to collecting and exhibiting contemporary art in Australia. View the museum’s works by rising Australian artists such as James Angus. The glossy white Manta Ray on display is one example of Angus’ three-dimensional art created using high-tech equipment and synthetic materials.

It’s time to enjoy a twilight Bridgeclimb. After you’ve been briefed, breath-tested, put through the paces on a climb simulator, and strapped into safety equip-ment, you’ll make your way across catwalks, ladders, and arches to the top of Sydney’s “old coat hanger,” the Harbour Bridge, 130 metres above sea level. As the sun dips below the horizon and the night sky turns to swirls of orange, pink, and purple, you’ll enjoy an unimpeded view of this picturesque city as it comes to life at night.

Cab it back to the wharf to Otto Ristorante Italiano for a relaxing dinner overlooking the water. Sample the zucchini flowers stuffed with creamy salt cod or the baby pink snapper with fennel and mint salad. For dolci, try the excellent cheese selection or allow a light panna cotta, mousse, or gelato to dance across your tongue. It’s been an energetic day, so it’s fortunate your hotel room is just upstairs. Sink into the oversize bathtub for a luxurious soak before bed.

DAY TWO / After a well-earned sleep-in, take a short cab ride to the popular Bills in Darlinghurst. Something of a Sydney institution, unassuming Bills has fans as far-flung as New York and London. Have a seat at the large communal table and dig into an indulgent breakfast of sweet corn fritters or fruit muffins.

Once sated, take a short walk to the eclectic eastern-suburb shopping precinct of Oxford Street, Paddington, and indulge in a spot of retail therapy where the well-heeled locals do. This is a good place to pick up clothing by talented Australian designers: Drift from the spangles and sequins of Charlie Brown to Sass and Bide’s urban déshabillé. If you’re looking for treats to take back home that don’t scream “souvenir,” Giftica has unusual beadwork mobiles, jewellery, and body balms.

Also beloved by locals is the nearby tree-lined stretch studded with cafés and delicatessens that is Queen Street Woollahra (walk southeast along Oxford to a left onto Queen). Step into the cool hush of Shapiro Auctioneers, which houses a seductive range of Australian and international paintings, sculpture, and photography.

The knowledgeable Jane Raffan can introduce you to some of the finest examples of Aboriginal art here. Find something you fancy? Shipping to your destination back home is, as they say in Australia, “no worries.”

You’re lunching at the cutting-edge, Thai-inspired Longrain restaurant, tucked inside a 100-year-old warehouse in the heart of Surry Hills. In the early days of the colony, this was a slum area thick with brothels, gangs, and sly grog shops, but Surry Hills now hums with art galleries, antiques shops, cafés, pubs, and fashion outlets. Sample the betel leaf topped with smoked trout and glistening orange globes of trout roe and an innovative dish that combines a tangle of prawns, pork, peanuts, sprouts, mint, and coriander under a net of drizzled egg.

Walk to the World Square monorail stop a few blocks away and enjoy the bird’s-eye view of the city’s landmarks as you make your way to the vast Australian National Maritime Museum, alighting at Harbourside. Exhibits include one of the original anchors from Capt. Cook’s Endeavour that the explorer jettisoned when he ran aground on the Barrier Reef in 1770. Then there’s the boat made entirely of beer cans and The Spirit of Australia, designed on a kitchen table and built in a Sydney backyard.

Take a short ferry ride from Darling Harbour to Circular Quay and wend your way through The Rocks district toward Sydney Observatory, built in 1858. You’re in for a truly celestial experience: Under the guidance of an experienced astronomer, you’ll gaze through powerful telescopes at distinctive constellations like the Southern Cross, or Crux, that twinkle in the Southern Hemisphere heavens. This month, the planets Mercury and Saturn will disappear from the sky, but Mars and Jupiter will remain tantalisingly visible.

Outside, take in the city panorama from Observatory Hill before making your way back down the steps and through the Argyle Cut toward George Street. You have dinner reservations at the sophisticated Rockpool, which offers ever-changing tasting menus to satisfy the palate. Typical dishes include goat cheese tortellini with pine nuts and raisins, tea-smoked duck with mango, star anise, and ginger caramel sauce, and rose-wrapped vanilla cream with candied pistachio and raspberries. Though the restaurant prides itself on its seafood, mouthwatering vegetarian options are also available.

DAY THREE / Order up a room service breakfast and brace yourself for an exhilarating morning. Your ride on Sydney’s wild side starts with a guided Harley-Davidson tour to Bronte Beach with Blue Thunder DownUnder, which you organised through the concierge. Don’t be nervous: Ninety percent of the people who climb aboard have never travelled by motorbike, and all riders are fully accredited with the relevant transport authority.

Breeze through suburbs including edgy Kings Cross and pricey Double Bay (dubbed “Double Pay” by locals due to the price tags in its upmarket boutiques) before stopping at Watsons Bay to stretch your legs. Climb the steps up to The Gap nearby for the sweeping ocean views back to the city. Then continue your winding journey to Bronte Beach, beloved for its bodysurfing waves and beachfront cafés, where you’ll bid farewell to your ride.

Keep your eyes peeled for Aboriginal rock carvings as you follow the cliff-top walk round to Bondi Beach. The popularity of this beach, even during the chill of winter, makes it hard to imagine that “sea bathing” here remained illegal until 1902.

Reward the morning’s exertion with a leisurely lunch at Icebergs Dining Room and Bar. Regulars recommend the “cartoccio”: stingray, silverbeet, white asparagus, and shiitake mushrooms steamed with broth in a paper bag. Afterward, return to the hotel for some relaxation. Head for the indoor swimming pool or spa, lounge on the sun deck, or stroll to nearby Spa Chakra, a holistic retreat that’s one of Australia’s best, for a massage, body polish and wrap, or hydrotherapy session.

Now that you’re rebalanced and reinvigorated, turn your thoughts to the evening ahead, which will be spent exploring Sydney’s underbelly through Destiny Tours. From the back seat of a converted Cadillac hearse, visit some of the sites most revealing of this city’s rough and raw history, such as the string of elegant but supposedly haunted buildings stretching down Macquarie Street and the former Darlinghurst Jail, where hangings took place. The tour also includes a visit to one of Sydney’s more famous bondage parlours, The Kastle, so if you’re of a sensitive disposition, you may wish to remain outside.

Have you worked up an appetite? Stop by Harry’s Café de Wheels, an old-fashioned pie cart so integral to the late-night Sydney scene that it has National Trust status. Some of the famous faces who have shared the ketchup bottles here include Frank Sinatra, Elton John, and Olivia Newton-John. Join the locals and the seagulls perched on the wharf and sample one of Harry’s specialties, a beef pie cooked with mushy peas.

Now that your three perfect days in Sydney are almost at an end, enjoy a drink at the Water Bar at your hotel before turning in for the night. This award-winning drinking hole is renowned for its innovative cocktail list, and, if you’re still feeling peckish, an upmarket bar-food menu featuring tapas-style dishes like Sydney rock oysters, dusted calamari, and carpaccio of salmon is also available. Settle into one of the low-slung lounges, raise your glass, and toast the harbour city’s beauty and complexity.

Denise Cullen, a longtime Hemispheres writer based Down Under, also contributes to The Sydney Morning Herald, The Age, and The Australian.