48 Hours in Sydney

From colonial mansions to glass-walled brasseries, prime real estate rims Sydney Harbour, all competing for a glimpse of the water. Capital of the Australian state of New South Wales and a major Pacific hub riding the Asian boom, Sydney seems recession-proof. The redevelopment of the old wharves continues to transform the waterfront while still ensuring historic districts retain their character. “Sydney is a modern city with an ancient heartbeat,” says city historian Lisa Murray. “The Eora, Sydney’s first peoples, enjoyed the harbor lifestyle for thousands of years, and Sydney is still defined by its harbor and rivers.”

What to do The city’s focus remains Circular Quay, landing site for the convict-laden vessels from Britain, which founded the penal colony in 1788. From the busy terminal, ferries come and go under the Sydney Harbour Bridge or around the Sydney Opera House. Grand plans to revamp the venerable Opera House are in the works, but new dining venues, such as the outdoor Opera Bar, are already breathing new life into the precinct.

On the other bank of Circular Quay, the Museum of Contemporary Art reopened in March after adding a new wing. The resulting streamlined spaces flanked by harbor-view windows host exhibitions by Australian notables (sculptor Stephen Birch, neon artist Peter Kennedy) as well as global art stars (Annie Leibovitz, Anish Kapoor).

Behind the museum lies the Rocks, early Sydney’s center. “It was Sydney’s most cosmopolitan place in the 19th century, a working district which welcomed, and also at times abused, the ships and sailors of the world,” says Murray. Press gangs would kidnap hapless sailors along the Rocks’ cobbled alleys, where visitors on weekends now shop for boomerangs and other Australian-made products at the Rocks Markets and spice blends and hand-pressed olive oils at the new Fridays-only Foodies Market. So-called bond stores once stocked with brandy, tobacco, tea, and flour currently house art galleries, boutiques, restaurants, and watering holes such as the Argyle, the epicenter of nightlife in the Rocks, with its multiple bars and live music.

Bordering the Rocks to the north, the old commerce-focused wharves of Walsh Bay have become the city’s arts hub. At Wharf 4/5, the Sydney Theatre Company produces new Australian plays and classic works under the artistic guidance of Cate Blanchett, while the contemporary Sydney Dance Company runs drop-in ballet, jazz, and hip-hop classes.

The waterfront rejuvenation began at Darling Harbour, where a host of attractions include an 1874 tall ship, one of only four of its kind in the world and on permanent display as part of the Maritime Museum. Go for a last ride on the iconic monorail that loops from Darling Harbour to the city center, destined to be torn down in the next year or two and turned into scrap metal—a government decision that shocked the city.

But taking to the water remains the best way to appreciate the harbor. Catch a ferry from Circular Quay to Cockatoo Island, Sydney’s new favorite harbor island since the former prison and dockyards opened to the public. Tour the heritage buildings, attend a concert or art exhibition, or join the sunset hubbub at the Island Bar, which is constructed from recycled shipping containers.

Alternatively, the classic ferry ride to the famous surf beach at Manly cruises the length of Sydney Harbour before docking at Manly Wharf. Swim, sign up for a surfing lesson, or leave the crowds and rent a kayak next to the wharf. Paddle around Manly Cove’s forested headlands to the secluded inlets and sheltered beaches of Sydney Harbour National Park. Landlubbers can hike the Manly Scenic Walkway. The national park also contains the historic buildings of Q Station, an old quarantine outpost that once cloistered passengers from contagion-hit ships, now a boutique hotel and a popular venue for weddings and conferences.

Where to shop For indie shopping, wander the Victorian streetscapes of inner suburbs Paddington, Woollahra, Newtown, and Surry Hills. Saturday’s Paddington Markets has been in operation for the past 37 years. Vendors hawk everything from watercolor paintings and antique silverware to little girl dresses in eucalyptus print fabric. Many of the designers graduate to the boutiques spread out along Paddington’s Oxford Street, such as Dinosaur Designs, makers of hand-sculpted jewelry. Local fashion labels like Neil Grigg Millinery and Jiva reside on adjoining William Street.

In Surry Hills, Grandma Takes a Trip stocks vintage dresses, coats, and accessories from the 1950s to the ’70s.

Though a long way from the outback, Sydney has plenty of Aboriginal art galleries selling classical dot paintings and contemporary works. The Artery in Darlinghurst specializes in art from such remote Aboriginal communities as Utopia, Mount Leibig, and Pupunya in the Northern Territory, and Kate Owen Gallery in Rozelle features emerging and established artists, including Clifford Possum, whose larger dot canvases set auction records at Sotheby’s.

Where to eat The food truck scene has finally hit Sydney as the city recently approved ten new mobile vendors. Find organic spelt pizzas, gourmet fish tacos, hot chocolate cakes, and more rolling out to fill late-night dining voids in locations like Circular Quay and Pitt Street Mall. The Eat Art Truck serves kingfish seviche and doubles as a street art canvas. The granddaddy of Sydney food trucks, Harry’s Cafe de Wheels has sold meat pies smothered in peas and gravy, a unique local offering, since 1945. It sits incongruously adjacent to Woolloomooloo Finger Wharf, now one of the city’s most exclusive residential and dining complexes.

The Opera Kitchen at the Opera House has hit on a winning formula: Combine outlets from some of Sydney’s best known gastronomic brands to form the fanciest food court in town. The wagyu burgers may be a tad expensive, but the harbor views are priceless. Highlights include the sushi bar at Kenji, the plank-roasted king salmon at Cloudy Bay Fish Company, and tiger prawn and green mango rice paper rolls at Misschu.

Gastro Park in Kings Cross has set local foodies abuzz since opening last year. The dining room’s clean lines frame the innovative, intricately styled food, which is anything but casual. Grant King, former executive chef at the seafood-inspired Pier restaurant, produces such playful and adventurous dishes as snapper fillet topped with crunchy fried fish scales.

Sydney has no shortage of waterfront dining, but it’s worth the trip to Bondi for Italian-inspired dishes at Icebergs Dining Room and Bar, on the top floor of the famed swimming club at the end of the beach. A favorite: Berkshire pork cutlet with grilled radicchio.

For the more price-conscious, Chinatown offers other cuisines beyond Cantonese. At Mamak, Malaysian chefs twirl and stretch dough into giant paper-thin sails before folding and slapping them onto the griddle. The ensuing crisp, flaky roti bread is perfect for dipping in rich coconut curries.