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Days 1-3: Begin in Melbourne

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After a decade-long revival, this boomtown has emerged as the continent's capital of cool. It's as vibrant as the rainbow yarn bombs that often decorate trees in City Square—and easier to navigate than its glamorous northern sibling. It's a place where food is celebrated, where the flat white will convince you to leave drip coffee behind forever, and where subcultures thrive in café-lined laneways. Most of all, its the optimism and independent spirit that best recommend Australia's second city.
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Wellington Parade, East Melbourne VIC 3002, Australia
Located an easy 10-minute walk southeast of the CBD, Fitzroy Gardens is one of Melbourne’s quaintest green spaces. Featuring avenues of elegant elm trees and paths paved in the shape of a Union Jack, this 64-acre, picnic-perfect parkland is...
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637-641 Chapel St, South Yarra VIC 3141, Australia
Considered one of Australia’s best living painters, John Olsen is famous for his squiggly-lined watercolor and oil renditions of the antipodean landscape, often marked by a big hot sun or a central body of water. The second property in the...