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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.

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.

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.

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.

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.

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.