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You won’t find any rustic treasures in the antiques shops that line this leafy street downhill from Paddington’s Oxford Street. Items here are super expensive, such as Louis XIV clocks, original Colonial prints, 18th-century Persian rugs, and estate jewellery. Even if your wallet is drained, it’s still a fun place to window-shop and there are some excellent cafés nearby.

The immense wealth of “Double Pay” is almost a joke; people call it the plastic surgery capital of Australia. To the west is exclusive Darling Point, where you’ll find Major Mitchell’s (see A Walk from Circular Quay to the QVB) former harbourside residence on Carthona Avenue. To the east is Point Piper, which was home to Sir Lawrence Hargrave (see Hargrave’s Box Kites) from 1902 to 1915. In between is Steyne Park and the delightful Redleaf Pool, just below the lovely Blackburn Gardens on New South Head Road. William Street, Bay Street and New South Head Road border the main shopping precinct, where you’ll find all the best international retail stores.

The largest cove in Sydney Harbour is embraced by Point Piper to the west and Vaucluse to the east. Northeast of Point Piper is Shark Island (see The Islands). To the east is Hermit Point, reputedly the haunt of a reclusive former convict. In 1942 a Japanese submarine lobbed shells into Rose Bay, presumably aiming for the former flying-boat base; it’s still the base for Sydney Harbour’s seaplanes (see Sailing on Sydney Harbour). If you’ve followed New South Head Road over from Double Bay, you’ll enjoy the walk along the waterfront from Rose Bay Park to Lyne Park.

Nielsen Park makes its way from winding Vaucluse Road down to Shark Bay, so named for the sharks caught here in the days before shark nets. In the centre of the park is the Mt Trefle Walk, and near the beach are changing pavilions, a great kiosk, Greycliffe House and a memorial to the Harbour Foreshore Vigilance Committee (see Harbourside Walks). The Hermitage Foreshore Walk starts west of Shark Beach, and offers some of the best views of Sydney as it meanders along the shoreline back to Rose Bay via Hermit Point. Don’t forget to carry your swimming gear.

After WC Wentworth’s (see Wentworth, Blaxland & Lawson) daughter was married, her husband commissioned the architect John Hilly to construct this Gothic residence. However, the couple left for England before its 1851 completion. It later became a home for mothers and babies, before the NSW government purchased the property in 1911. The ground floor is now open to the public, while the NPWS (see The Islands) occupies the rest of the building.

William Charles Wentworth purchased this property, built in 1803, in 1827. Wentworth was a major figure in the early colony – a barrister, explorer and statesman, he railed against the privileges enjoyed by the English-born colonists and lobbied for self-government. The Wentworths lived in this Gothic house until 1861. It has been a public museum since 1910.

Named after Robert Watson, the quartermaster on the HMS Sirius (see A Walk from Circular Quay to the QVB), this bay has been the base for Sydney Harbour’s pilot boats since the 1800s. Uphill from Robertson Park are the Greycliffe Memorial Gates, which commemorate the 41 people who lost their lives when the ferry Greycliffe went down in 1927.

Just north of Watsons Bay is Camp Cove, where Governor Phillip spent the night after decamping from Botany Bay (see First Fleet Arives & Captain Cook's Landing Place) and entered Port Jackson for the first time. A track leads from the kiosk at the northern end of this protected beach over to tiny male-nudist Lady Bay Beach, which is overlooked by the HMAS Watson Naval Base. At the end of the track is South Head’s Hornby Lighthouse and several old gun emplacements (see South Head). This windswept headland offers spectacular views out to sea, across to Manly and the North Harbour.

Perhaps Sydney’s most infamous headland, this bluff, overlooking the ocean and the wave-lashed rocks far below, has seen more than its fair share of suicides. South of The Gap is the rusting anchor of the Dunbar (see Dunbar Sinks) and further south again is Jacob’s Ladder: the sole survivor of the 1857 Dunbar tragedy was hauled to safety up this cleft in the rocks. Further south again is the signal station that has been monitoring shipping in and out of Sydney Harbour since 1848.

This lighthouse on the grassy, windswept clifftops was built between 1816 and 1818 to Francis Greenway’s (see Francis Greenway: Convict Architect) design. It was the first of many projects Greenway completed for Governor Macquarie, earning him a conditional pardon. After more than 60 years of service the stately Doric tower fell into disrepair, and in 1880 the architect James Barnet (see Darlinghurst Court House & Old Darlinghurst Gaol) redesigned the lighthouse. Although almost a perfect copy of the original, the new lighthouse featured several technological advances when it opened in 1883, including an electric lantern.

Macquarie Lighthouse