New South Wales (Sydney Region)
Kings Cross, Elisabeth Bay & Potts Point
The preserve of Sydney's bohemians in the 1950s, Kings Cross became an R&R spot for American soldiers during the Vietnam war, and it is now Sydney's red-light district, its streets prowled by prostitutes, junkies, drunks, strippers and homeless teenagers. It is also a bustling centre for backpackers and other travellers, especially around leafy and quieter Victoria Street; the two sides of "the Cross" (as locals call it) coexist with little trouble, though some of the tourists seem a little surprised at where they've ended up, and it can be rather intimidating for lone women.
The Cross can seem threatening but the constant flow of people makes it relatively safe, and it's always lively, with places to eat and drink that stay open all hours. Climbing up William Street from Hyde Park, Darlinghurst Road beckons with its giant neon Coca Cola sign. At weekends, an endless stream of ice-cream-licking suburban voyeurs, disgorged from the underground Kings Cross train station, trawl along the Darlinghurst Road strip to the El Alamein fountain in the shady Fitzroy Gardens as touts try their best to haul them into tacky strip-joints and sleazy nightclubs. Kings Cross is much more subdued during the day, with a slightly hung-over feel to it: local residents emerge and it's a good time to hang out in the cafés. There's a small arts and crafts market in the Fitzroy Gardens on Sundays.

Walking tours of the Cross leave from the El Alamein fountain at 10.30am on weekends ($14; 2hr) and explore the celebrity and crime connections of the area; alternatively pop into the Kings Cross library off the gardens and pick up a free Kings Cross Walking Tour map.

From the Fitzroy Gardens, the sin strip ends and tree-lined Macleay Street runs through quieter, upmarket Potts Point, with its Art Deco residential apartments, classy hotels, stylish restaurants and occasional harbour glimpses over wealthier Elizabeth Bay, just east. Beyond Macleay Street, Wylde Street heads downhill towards grittier Wolloomooloo.

Elizabeth Bay House
Barely five minutes' walk northwest of Kings Cross Station, Elizabeth Bay is nevertheless a well-heeled residential area, centred around Elizabeth Bay House, at 7 Onslow Ave. The grand Greek Revival villa was built between 1835 and 1839 for Alexander Macleay, Colonial Secretary of New South Wales. The large Macleay family, who arrived from Britain in 1826, included two sons and six daughters: all were obsessed with botany or etymology, and the original 54-acre waterfront grounds were said to be a botanist's paradise. The Macleay Museum at Sydney University was formed from the Macleays' natural history collection. The views from the windows of the yachts and water of Elizabeth Bay are pretty stunning. (Tues-Sun 10am-4.30pm; $6)

Woolloomooloo
North of William Street just below Kings Cross, Woolloomooloo occupies the old harbourside quarter, between The Domain and the grey-painted fleet of the Garden Island Naval Depot. Once a narrow-streeted dockside slum, Woolloomoloo is slowly being spruced up, though luxury housing developments live uneasily side by side with problematic community housing, and you should still be careful at night in the backstreets. There are some rowdy pubs and some old-fashioned quiet locals, as well as the legendary Harry's Café de Wheels on Cowper Wharf Road, a 24-hour pie-cart operating since 1945. Famous for pea and pie floaters, Harry's has become a gathering place for Sydney cabbies and hungry clubbers in the wee small hours. 

Nearby, the once picturesquely dilapidated Woolloomooloo Finger Wharf, dating from 1917, no longer handles immigrants or cargo. Plans to demolish it were met with fierce protests, but the compromise - its redevelopment as sanitized luxury residential apartments - hasn't pleased many Sydneysiders either. Woolloomooloo is best reached by foot from Kings Cross by taking the McElhone or the Butlers Stairs from Victoria Street - just follow the constant stream of white-clad sailors.