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Experiment Farm Cottage
This colonial bungalow (c.1835) was built on the site of the first land grant issued to a convict. Only a year after arriving, Governor Phillip granted 12 hectares of land to James Ruse in an experiment in self-sufficiency. Just down the hill, Hambledon Cottage (9635 6924; 63 Hassell St; - Wed-Sun) is older still (1824) and surrounded by nearly 200-year-old camphor laurels and English oaks.
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Finger Wharf
A former wool and cargo dock, the Finger Wharf has emerged as one of Sydney's most stellar eating, drinking and sleeping addresses. A slick five-star hotel, some marvellous eateries and stratospherically priced apartments have transformed this working-class wharf into a star-spotting paparazzi haunt. At the end of this wharf is Russell Crowe's penthouse.
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Fitzroy Gardens
It's testimony to the 'cleaning up' of the Cross that this once decidedly dodgy park is now a reasonably pleasant place to loiter (probably helped by the Stalinist police station at one end). The dandelion-esque El Alamein Fountain (1961) is one of the area's most notable landmarks, known locally as 'the elephant douche'. On Sundays a small flea market sets up in the plaza.
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Fort Denison
Fort Denison is a small island off Mrs Macquaries Point. It was originally used to isolate troublesome convicts, until it was fortified in the mid-19th century during the Crimean War. It now has a cafe and, in terms of views and location, may be one of the best places to have coffee in all of Sydney. Take your pick of tours. Bookings are essential.
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Gannon House
Purchasing works directly from aboriginal communities, Gannon House (named after colonial builder Michael Gannon) takes an umbrella approach to its gallery exhibits, jumbling aboriginal artefacts, paintings and didgeridoos with contemporary white Australian abstract art. The results are surprisingly harmonious.
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Garrison Church
Also known as Holy Trinity (1843), this lovely sandstone Anglican church at the west end of the Argyle Cut was the colony's first military church. It's a charming place, lined with regimental flags, and it's also wheelchair accessible. The first prime minister of Australia, Edmund Barton, received his primary education in the school house which is now the parish hall; the sandstone walls are nearly 80cm thick.
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Goat Island
The largest island in the bay, Goat Island, west of Sydney Harbour Bridge, has been a shipyard, quarantine station and gunpowder depot in its previous lives. There are different tours of Goat Island - Heritage tour, Gruesome Tales tour or Picnic Day tour. All tours are booked at, and depart from, the park's office at Cadmans Cottage located at 110 George St, The Rocks, 9247 5033.
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Government House
Government House (1845) is the third of five structures that have served as the official residence of the governor of New South Wales. It dominates the western headland of Farm Cove and plays host to visiting dignitaries, including heads of state and royalty. The governor, who now resides in Admiralty House, still uses it for weekly meetings. It's a marvellous example of the Gothic Revival style.
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Governors Phillip & Macquarie Towers
Plans were drawn up in the 1980s to develop the site of Governor Phillip's first Government House which had been left semi-derelict for 50 years. At the north end of the block the remaining foundations of Government house were converted into First Government House Plaza and the Museum of Sydney. Governor Phillip Tower (1993) is Sydney's 6th tallest office block; at 227m it's only 3m shy of the tallest.
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Great Synagogue
The Great Synagogue was built in 1878 and houses Sydney's longest-running congregation. It's considered the Mother Synagogue of Australia and architecturally the most important in the southern hemisphere. The impressive ceiling features gold-leaf stars on a night-blue background supported by ornate white and gold columns forming 12 arches representing the tribes of Israel. The general public can only visit via tours.
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Green Park
Green Park is a pleasant place during the day but best avoided after dark. A large illuminated pink triangle backed by black pillars is the Gay & Lesbian Holocaust Memorial. It was founded by the late Dr Kitty Fischer, who as a young Jewish girl in Auschwitz was kept alive by food smuggled to her by a gay inmate. At another corner of the park is a memorial to Victor Chang, the famed heart surgeon who worked at neighbouring St Vincent's Hospital.
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Harbourside
The first big Darling Harbour development, Harbourside is like that guy in a trendy nightclub still wearing a pirate shirt and an unreconstructed mullet; its 1980s stylings are no match for the chic constructions loitering on the other side of the harbour. Restaurants line the frontage and a food hall and shops selling cheap clothes and souvenirs fill the interior.
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History House
This beautiful Victorian townhouse, completed in 1872 by architect George Allen Mansfield, has housed the Royal Australian Historical Society since 1970. The library is open to researchers, for a fee; otherwise there's no public access. Just down the block at 145 Macquarie St is a similar building quartering the Royal Australian College of Physicians.
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Hogarth Galleries
A cultural beacon in an obscure Paddington laneway, Hogarth has supported and promoted aboriginal art since 1972. Honouring established artists and sourcing up-and-comers, Hogarth exhibits contemporary dot paintings, basketry, framed prints, fabrics, spears and didgeridoos.
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Hyde Park
Hyde Park is a refreshing green space within the city centre. The tree-formed tunnel running down the middle is particularly lovely to walk through at night, illuminated by fairy lights. At the southern end the Pool of Reflection leads to the Anzac Memorial and the richly symbolic Art-Deco Archibald Memorial Fountain is at the northern end. Cafés at either end offer alfresco dining, and there's a popular life-sized chess set near St James.
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Hyde Park Barracks Museum
Francis Greenway designed this squarish, decorously Georgian structure (1819) as convict quarters. It later served in turn as an immigration depot, an asylum for women, and even law courts. Now it's a fascinating, if not entirely cheerful, museum focusing on the various phases of the barracks' history. Read about some of the offences that got people transported to Australia, or added to their time and punishment once they arrived.
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Italian Forum
This recreation of an Italian piazza has had its fair share of criticism and compliments, and yes, it is a bit cheesy (think Disney does Italy), but the Italian Forum is a good place to partake in fairly authentic Italian grub. Order a gelato or macchiato, check everyone out and remember to say 'ciao' a lot. The Forum is home to shops, family-friendly restaurants and a library.
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Jubilee & Bicentennial Parks
At the northern tip of Glebe Point Rd these two large grassy parks merge together, offering good views across the bay to Rozelle. Fig and palm trees dot the landscape and mums and dads stroll along with their kiddies. A new pathway leads along the shoreline to Blackwattle Bay, passing the Victorian Italianate Bellevue Cottage (1896) and a new park set around the temple-like ruins of an industrial incinerator.
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Juniper Hall
This magnificently restored Georgian mansion on Oxford St was built by Robert Cooper as a family home in 1824 with profits from his gin business. He named it after a key gin-making ingredient. Paddington's oldest home, it's owned by the National Trust but tenanted as a shop specialising in antiques and decorative arts; there's nothing to stop you having a nosy inside during opening hours.
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Justice & Police Museum
Based in the old Water Police Station (1858), this museum focuses on crime, policing and the Australian legal and penal system, at once fascinating and depressing. Displays include forensic evidence from famous crimes of the past, some nasty-looking weapons, lots of mug shots and at least two stuffed dogs. The museum has wheelchair access to the ground floor only, and Braille and audio guides are available.
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Ken Done Gallery
The cheerful, almost childlike work of Sydney artist Ken Done is displayed in a gallery in the wonderfully restored Australian Steam Navigation Building. Expect plenty of vividly coloured, uniquely Australian landscapes and seascapes, plus lots of works that depict the daily minutiae of Done's rather charmed existence.
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King St Wharf
Cockle Bay Wharf in ultramodern metal drag, this wharf continues the Darling Harbour precinct past the Pyrmont Bridge on the city side. All the luxury apartments in this A$800 -million development are sold and the office space leased out, but you can still get a taste of the high life at its strip of bars and restaurants.
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Kirribilli Point
Until the reign of John Howard, Australian prime ministers lived at The Lodge, in Canberra. Here on Kirribilli Point you'll find the PM's contentious Sydney residence, the Gothic Revival-style Kirribilli House (1854). The governor general's digs are in Admiralty House (1846), the one everyone dreams of living in if it came without the job. Both houses are better spotted from the water than attempting to peer through the heavily-guarded gates.
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Ku-Ring-Gai Chase National Park
This 14,978-hectare national park is 24km north of the city centre and has that classic Sydney mixture of sandstone, bushland and water, plus walking tracks, horse-riding trails, picnic areas, Aboriginal rock engravings and spectacular views of Broken Bay. The park has over 100km of shoreline and several through-roads (enter Bobbin Head Rd, North Turramurra; Ku-Ring-Gai Chase Rd off Pacific Highway, Mt Colah; or McCarrs Creek Rd, Terrey Hills).
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Lane Cove National Park
This 601-hectare park lies 10km northwest of Sydney's centre and is good for bushwalks. It's home to dozens of critters including some endangered species of owl and toad. The best time to visit is in spring, when the water dragons are about and the native orchids and lilies are in flower. The Lane Cove River is great for rowing boats and kayaks, but swimming is inadvisable. You can cycle and camp, and wheelchair access is available in parts.
