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Darlinghurst Road runs from the court house to the Alamein Fountain. “The Wall”, a sandstone wall running beside the gaol, is a nocturnal beat for male prostitutes. The pleasant Green Park is thought to be named after a former hangman at the gaol, Alexander “The Strangler” Green. Beyond the park is a colourful strip of terrace houses, hotels and cafés that ends at William Street. In the 1920s and 30s the area beyond William Street had some bohemian charm, but since WWII it has been Australia’s most notorious red-light district.

The Australian Museum is just the place for those parents with Jurassic-obsessed youngsters. The museum conducts tours of the museum and runs special events, workshops and activities for children on weekends and school holidays. Kids might take part in a “mini dinosaur dig,” climb into a hot air balloon, learn how to create their own fossil cast, or enjoy the interactive Kids’ Island.

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.

This dandelion-shaped fountain in the Fitzroy Gardens is especially pleasant when illuminated at night. Though many consider it overrated, it is still probably Sydney’s most popularly known public artwork. Designed by Robert Woodward in 1961, it commemorates the participation of Australian soldiers in the Battle of El Alamein in Egypt during WWII, which precipitated Germany’s defeat in North Africa.

Alexander Macleay, Colonial Secretary of NSW from 1825 to 1837, had architect John Verge design this residence for his large family in 1839. Macleay was also a distinguished botanist and the first president of the Australian Museum. This Greek Revival residence is said to contain the finest example of a Colonial interior anywhere in Australia. Macleay’s family subdivided the original 23 ha (56 acres) of land following his death. In 1941 the house was further divided into 15 apartments. The NSW government purchased the property in the 1960s and the Historic Houses Trust undertook major restoration. It finally re-opened as a museum in 1977.

This lovely reserve on White Horse Point, overlooking Cockatoo Island, is best known for the Dawn Fraser Pool, one of Sydney’s oldest municipal pools. Dawn Fraser is a local legend, as much loved for her candid take on life and wild streak as she is for having dominated the pool at the 1956, 1960 and 1964 Olympic Games, leaving 40 world records in her wake. Although prone to tidal fluctuations, the pool is pleasantly unpretentious and a good place to strike up a conversation with an old-time local.

One of the best spots to drop a line is at the Ives Steps Wharf, just under the Sydney Harbour Bridge west of Dawes Point Park. This is a popular haunt for chatty older anglers who are happy to share their knowledge with children. A store, Gowings, sells bait and tackle.