The inner-eastern suburbs begin just beyond the Domain and include Kings Cross, the old maritime suburb of Woolloomooloo, Paddington and Darlinghurst, once the haunt of some of the city’s most notorious gangsters and now home to some very trendy cafes and restaurants.
Get there by bus or take the stairs near the Art Gallery in Mrs Macquaries Road. The ’Loo’s most recent and controversial development is the Finger Wharf, once known for toughness and lawlessness but now one of Sydney’s most exclusive addresses. Try Harry’s Cafe de Wheels, a piewagon and long-time Sydney icon on the eastern side of the bay.
If driving to Kings Cross, head towards the Coca-Cola sign – a landmark since the days of the Vietnam War.
The Cross is one of the most fascinating parts of Sydney. At night, when the strip clubs of Darlinghurst Road swing into action, the vibe is raw and edgy.
But by daylight it retains the charm of its bohemian past, with gracious tree-lined streets and pretty sidewalk cafes. Look for the El Alamein Fountain, the most photographed fountain in Sydney.
Elizabeth Bay House
Designed by John Verge as a home for Alexander Macleay (whose family history is displayed on the walls of St James Church in Queens Square), the house is particularly famous for the stunning proportions of its elegant oval saloon with a sky-lit dome, and beautiful curving staircase.
After spending many years as a shabby boarding house and artists’ squat, it is now a Historic Houses Trust museum, and its rooms have been restored to their former 19th-century graciousness.
7 Onslow Ave, Elizabeth Bay; open 9.30am–4pm Fri–Sun.
Considered an eyesore until quite recently, Paddington is now one of Sydney’s most beautiful suburbs. Its backstreets are lined with rows of iron-lace-trimmed terraces decked with flowers, and its main thoroughfare, Oxford Street, is home to dozens of boutiques, galleries and cafes.
Always busy, it is at its most vibrant on Saturdays, when the Paddington Markets are in full swing. Paddington is easily accessed by bus – you can disembark on Oxford Street and walk around.