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Begin at the El Alamein Fountain. Walk down Macleay Street and you’ll pass the Rex Hotel, site of Sydney’s first gay bar in the 1940s, the Bottoms Up. Turn into Greenknowe Avenue and walk down the hill and left into leafy Ithaca Road, where you’ll catch glimpses of the harbour. Beare Park is tucked between the high-rise apartments. From the wharf there’s a good view of Boomerang, the Spanish Mission mansion. Walk up Billyard Avenue to Elizabeth Bay House, passing the Del Rio, another Californian Spanish Mission building. Steps on Onslow Avenue will bring you back up the hill to Macleay Street.

Turning right, stroll down to Yellow Bistro . Have a coffee and a sweet treat on the porch.

Refreshed, walk down Challis Avenue into Embarkation Park for great views of the Naval Base at Woolloomooloo. Continue up Victoria Street, past the terrace houses to Hughes Street. Turn left into the Tusculum Street, and then Manning Street. Next door to Tusculum Villa, the Werrington and the Wychbury are some of the best Art Deco buildings in the Cross.

On your way back up Macleay Street, pop into Orwell Street to see the old Metro Theatre, where a nightclub roared in the 1930s. Finish up your afternoon tour with a drink at the Bourbon, a very stylishly revamped Kings Cross dive bar.

Offers an alternative to the mainstream gay clubs with a mixed crowd, excellent DJs, live electronic music and an anything-goes vibe.

Darlinghurst Road runs from the court house to the Alamein Fountain. “The Wall”, a sandstone wall running beside the gaol, is a nocturnal beat for male prostitutes. The pleasant Green Park is thought to be named after a former hangman at the gaol, Alexander “The Strangler” Green. Beyond the park is a colourful strip of terrace houses, hotels and cafés that ends at William Street. In the 1920s and 30s the area beyond William Street had some bohemian charm, but since WWII it has been Australia’s most notorious red-light district.

This groovy, gay and sleek corner caféé offers seriously good coffee and snacks. A popular meeting place to hang out and soak up the sun on their outdoor tables.

This dandelion-shaped fountain in the Fitzroy Gardens is especially pleasant when illuminated at night. Though many consider it overrated, it is still probably Sydney’s most popularly known public artwork. Designed by Robert Woodward in 1961, it commemorates the participation of Australian soldiers in the Battle of El Alamein in Egypt during WWII, which precipitated Germany’s defeat in North Africa.

Alexander Macleay, Colonial Secretary of NSW from 1825 to 1837, had architect John Verge design this residence for his large family in 1839. Macleay was also a distinguished botanist and the first president of the Australian Museum. This Greek Revival residence is said to contain the finest example of a Colonial interior anywhere in Australia. Macleay’s family subdivided the original 23 ha (56 acres) of land following his death. In 1941 the house was further divided into 15 apartments. The NSW government purchased the property in the 1960s and the Historic Houses Trust undertook major restoration. It finally re-opened as a museum in 1977.

Another haunt of the style set, this time with a distinct Melbourne twist. Servings of the Italian food are small, so make sure to order some homemade bread.