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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.
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