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One of Sydney’s first skyscrapers, this elegant 1920s apartment building has housed artistic notables such as artist Portia Geach and actor, writer and comic Barry Humphries.

More than five million items are held in the Library’s Mitchell (1910) and Macquarie (1988) Wings. The Exhibition Spaces explore this extensive collection and present free public seminars. Make sure to go on the excellent self-guided tour.

The oldest parliament house in the world began in 1816 as a wing of the “Rum Hospital”, built by contractors licensed to import rum into the colony in lieu of payment. The New South Wales Legislative Council held its first meeting here in 1829.

This structure replaced the central wing of the Rum Hospital in the 1880s. The statue of a boar, Il Porcellino , is a replica of a 1547 Florentine artwork.

Australia’s grandest banks reside on this broad plaza. A Cenotaph near George Street commemorates Australia’s war dead, and The Passage by Anne Graham celebrates Sydney’s Georgian heritage.

An elegant museum and home to the Historic Houses Trust, this 1816 Rum Hospital wing was converted in 1854 into a branch of London’s Royal Mint.

Perhaps Francis Greenway’s finest work, these barracks were built in 1817 to house convicts. Later a hostel for immigrant women and then courtrooms, since 1979 it has been an interesting museum of the site and its varied occupants.

Built into a barrack wall is this memorial to the victims of the Famine (1845–48). This catastrophe forced 30,000 Irish women and over 4,000 orphans to migrate to Australia; some were housed at the barracks.

Another Greenway gem, this 1822 church was originally intended as a court house. Don’t miss the superb 1930s mural in the Children’s Chapel.

Governor Macquarie envisaged this small square as Sydney’s civic centre. In the 1890s it was a rallying point for protesters, among them Republicans who delighted in mounting Queen Victoria’s statue to address the masses.