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This Classical Revival Town Hall on Oxford Street was designed by J Kemp, a local architect who won an international competition to design a civic centre that matched the suburb’s increasing status. The main building was completed in 1891, and the clock tower that now dominates was added several years later. The hall underwent extensive restoration work in the 1990s and is no longer used by the council. But it does house the suburb’s library, offices, cinemas and a radio station. It is also a regular venue for private functions and corporate events.

The fertile soil found here in the 1780s spared the fledgling colony from probable starvation and spawned Sydney’s original satellite township. It was a rural retreat for Governor Phillip, who built a cottage here in 1790. Old Government House, which replaced Phillip’s cottage in 1799, is one of Sydney’s most historic sites. Other highlights include Experiment Farm Cottage, Elizabeth Farm, Hambledon Cottage (see Historic Sites & Townships) and Australia’s oldest cemetery, St. John’s. Here you’ll find the grave of “The Flogging Parson”, Reverend Samuel Marsden, the early colony’s notoriously sadistic magistrate.

Pittwater is a long, slender waterway running from Newport to Palm Beach (see Palm), Ku-ring-gai Chase National Park and Broken Bay. Exclusive houses, private wharves and public marinas populate its eastern shoreline. Housing on the western shoreline thins out as you head north, until you reach Ku-ring-gai Chase National Park, north of isolated Towlers Bay and exclusive Scotland Island. Pittwater’s sheltered waters have long been a favourite haunt with yachties. Broken Bay is a beautiful, wide and sometimes wild expanse of water dominated by Lion Island, an uninhabited rocky outcrop.

Portuguese custard tarts, natas , are found all over Sydney, but you haven’t really tasted them until you’ve tried Honeymoon Patisserie. Silvas offers traditional charcoal chicken and Gloria’s Café serves up great country dishes.

Prior to white settlement, the area from Broken Bay to Sydney Harbour was inhabited by the Guringai people. However, by the 1840s, most had been wiped out by smallpox or driven away. Over 800 sites record the Aboriginal culture and their bond with the land, including rock engravings, axe-grinding grooves, burial sites, cave shelters, middens (sea-shell mounds) and ochre hand stencils.

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.

Richard Rouse (1774–1852), Superintendent of Public Works and Convicts at Parramatta, once occupied this estate and was succeeded by seven generations of descendants. The 1813 Historic Houses Trust property features a convict-built Georgian residence, outbuildings and gardens. The furniture dates from the 1830s to the 1960s.

Proclaimed in 1879, this is Australia’s oldest national park and the world’s second oldest. The 15,074-ha (37,248-acre) park is 32 km (19 miles) south of Sydney. Here you’ll find subtropical rainforests, deep valleys, cycle and walking trails, rugged ocean beaches, sandstone clifftops, heathlands, mangroves and inland lagoons. There are several picnic- and campgrounds, and if you’re lucky you could spy a swamp wallaby, a satin bowerbird, a pied oystercatcher or the endangered tiger quoll. A tram from Loftus Station connects with the visitors centre on Sundays and public holidays.