In some ways, though, the city delights in its "bad-boy" heritage. Though the region was populated for 100,000 years by the Aborigines, captain Arthur Phillips sailed his First Fleet into Sydney Cove in 1788, bearing nearly 1,000 exiled convicts from British prisons. Settled as a colony of the crown and named "New South Wales," the country grew as more exiled convicts joined free settlers in forming the basis for the community that would become a major financial and cultural center of the Asia-Pacific region.

Today, Sydney abounds with modern interpretations of its colonial past. At waterfront Circular Quay, where Phillips first landed, street entertainers ply their trade along Writer's Walk, where famous writers' words about Australia are fixed in the sidewalk with gold medallions.

The Rocks region has evolved in truly contemporary fashion, from the site of Australia's first permanent European settlement to its current incarnation as a leading shopping venue that offers some of the city's finest gifts, souvenirs and native crafts. It's also renowned for great restaurants and cheerful pubs. History continues to abound in adjacent Victorian suburbs, where a stroll through the cobbled streets and alleyways gives a visitor a sense of the former seaport region's rich colonial past.

Home to the Harbourside dining and shopping complex, the National Maritime Museum and the Sydney Aquarium, Darling Harbor invites visitors to meander as they enjoy free music and entertainment on weekends. Outlying beaches stretch for miles, and visitors join locals on the sparkling sand.