The Insiders’ Guide to the World’s Greatest Cities: Sydney

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Bondi Beach.

City Guide: Sydney

Virtuoso travel advisors share their can’t-miss highlights in Sydney.

A Henry Deane martini.
Sydney Harbour and the Sydney Opera House.

Sydney is big, brash, and beautiful – fashionable but unpretentious, outdoorsy and multicultured,” says San Francisco-based Virtuoso travel advisor John Stewart Bowerman, who has family there and visits often. Beyond its famed harbor, travelers fall for Sydney’s big-city-meets laid-back-surf-town vibe. And, with more than 100 beaches within city limits, there’s a spot in the sand for everyone. 
WHEN TO GO: “I love spring, which, in Australia, is from September to November,” says Bowerman. “Watching the sun rise over Sydney Harbour on a crisp morning is magic – and a great cure for jet lag.”
DON’T MISS: The Taronga Zoo is home to several native Australian animals, including kangaroos, koalas, and wombats,” says Sydney-based Virtuoso travel advisor Kelly Ayers. “It’s in Mosman, which is a gorgeous 12-minute ferry ride from the city.”
BEACH IT: “Head to Shelly Beach, near North Head, the northern part of land that juts out to form the entrance to Sydney Harbour,” Bowerman suggests. “It’s popular with locals and has a great Aussie feel, along with some of Sydney’s best snorkeling.”
DIG IN: Sydneysiders take their brunch very seriously. “I love the prix fixe Sunday brunch at Bondi Icebergs Club, which includes fresh pastries and bottomless prosecco,” Ayers says. “Beyond breathtaking views of Bondi Beach, you’re right next door to the must-do photo op at Bondi Icebergs swimming pool. Walk off your meal on the winding trek from Bondi to Coogee Beach.”
PRO TIP: “Henry Deane, a contemporary bilevel cocktail lounge in Millers Point [a ten-minute Uber ride from downtown], is a fantastic venue for mingling with locals,” Ayers says. “Order a coconut and pandan daiquiri for a bitter, sweet, and salty hit.”
BRING SYDNEY HOME: “The best Aboriginal art can be found in the gorgeous galleries and boutiques lining The Rocks, the historic center of downtown Sydney,” Ayers notes. “Spend an afternoon in the area and finish with a local beer at Sydney’s oldest pub, Fortune of War.”
STAY: See (or rather, taste) how Anna Polyviou earned her title as Australia’s 2016 Pastry Chef of the Year during afternoon tea in The Lobby Lounge & Terrace at the 565-room Shangri-La Hotel, Sydney. Virtuoso amenities include an upgrade at time of booking, breakfast daily, and a $100 dining credit.

More: The Insiders' Guide to the World’s Greatest Cities

Photos: Jason Loucas