Sydney is blessed with stunning ocean beaches, magnificent national parks and a wonderful subtropical climate that makes the great outdoors irresistible to its four million inhabitants. The Eora people, the Aborigines who settled around Sydney Harbour, arrived approximately 50,000 years ago, while the white settlers arrived just over 200 years ago. Free settlers soon followed in the wake of the First Fleet of transported convicts, and after them several waves of migrants seeking a new life. Now, two centuries later, the once far-flung penal colony has matured into a culturally diverse, tolerant and mesmerizing city. Ideally located on the world’s most beautiful harbour, Sydney is as exciting and bustling as it is laid back and relaxing.
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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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Nothing compares to Akira’s one-of-a-kind designs; his delicate and ephemeral garments are virtually art pieces and coveted by all. Check out his new menswear line.
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A neat shop sells the best local and imported streetwear.
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Presents the latest, most stylish and provocative in French cinema.
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Brett Whiteley.
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Designed by Sydney’s arbiters of style, Engelen Moore, Altair was voted the world’s best apartment building in 2001. The coup was clinched by its environ-mental performance and sleek lines. Mechanical louvres on the building’s façade open to catch the breeze.
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At this fun budget hotel, all rooms have cable TV and solid, comfy wooden furniture. There are discount weekly rates and a few top-quality backpacker rooms: they fill up quickly, so book them early.
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Morning
Catch the Bondi Explorer or a 325 bus from Circular Quay and get off at Nielsen Park. It’s a short walk downhill to Greycliffe House and Shark Beach. When you’re ready, walk back to Vaucluse Road, which becomes Wentworth Road. The entrance to Vaucluse House is further down on the right. Continue along Wentworth and take the first right into Chapel Road. WC Went-worth’s gloomy mausoleum is just up the hill on your left. Steps lead from behind the mausoleum to Fitzwilliam Street. Turn right and walk downhill to the lane on your left, which takes you across the Parsley Bay suspension footbridge. Take the steps on your left leading up to The Crescent and follow this around until you reach Palmerston Street, which leads to Watsons Bay Pilot Station. Follow Marine Parade north to the ferry wharf and lunch at Doyle’s (see Doyle’s On The Beach).
Afternoon
After lunch, walk to Short Street at the end of the beach, turn immediately left into Cove Street, and then left again into Pacific Street. This leads up to Green Point overlooking Camp Cove. After enjoying a swim here, or at Lady Bay Beach further on, follow the path along the clifftops to South Head. Retrace your steps and catch the ferry from Watsons Bay back to Circular Quay, or the bus from Hopetoun Avenue.
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On a street of designer names, this little shop and studio may not stand out. But it hand-crafts gorgeous shoes for men and women.
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Sydney’s style set love the slick renovation (see Botanic Gardens & The Domain). Outdoor, saltwater.
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Hotel price categories
For a standard double room per night (with breakfast if included), taxes and extra charges.
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