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Old Government House
The country residence of the early governors, this elegant Georgian Palladian building is situated in Parramatta Park. The earliest part dates from 1799, making it the oldest remaining public building in Australia. Entry is by way of an interesting hour-long tour around rooms furnished with original colonial furniture and painstaking reproductions. Phone for details about monthly ghost nights.
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Original & Authentic Aboriginal Art
This trustworthy gallery specialises in works from four specific regions - the Central and Western Deserts, Queensland, Arnhem Land and the Kimberleys - with info available on the artists, and some more unusual stuff for sale like painted glass and traditional sand paintings preserved on canvas.
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Outback Centre
A mixture of kitsch and cultural, this is a combination of souvenir store, performance space and art gallery. You'll find woomeras (spear-throwers), kalis (jumbo-sized boomerangs), musical clap sticks and bullroarers (ceremonial musical instruments). The highlight, hidden out back, is Australia's Outback Gallery. A free 'Sounds of the Outback' didgeridoo performance takes place at , and daily.
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Overseas Passenger Terminal
Passengers from luxury cruise ships like the QEII disembark here, so what better place to site ultra-fancy drinking and dining establishments? Quay is among the occupants of the architecturally dynamic modern terminal. For a great harbour view, head up to the observation deck housed in the turret at the north end.
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Paddington Market
A cultural experience not to be missed, these markets turn Saturdays in Paddington into pandemonium. Starting in the 1970s, Paddington Markets were a beacon for bohemians. It's more mainstream here now, but still worth checking out for the pricey cutting-edge fashions and vintage clothing, creative crafts, beautiful jewellery and tasty food.
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Parliament House
Twin of The Mint, Parliament House (1816), used by the Legislative Council of the colony from 1829, is still home to the Parliament of New South Wales, making it the world's oldest continually operating parliament building. The front section was originally the northern wing of the Rum Hospital. It blends into a modern addition on the east side.
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Parramatta
The second European settlement in Australia, Rose Hill was founded by First Fleet convict labour when Sydney Cove proved to be a poor area for farming. Sydney's reserves of glamour are running dry by the time you head this far west, but for those on longer stays in Sydney - particularly those with a historical bent - a river journey to Parramatta is an interesting diversion and a chance to see more of the 'real Sydney'.
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Powerhouse Museum
It can be tough finding your way here, but the payoff is huge. The zillion exhibits are very well displayed and always engaging, covering everything from language to industrial design to musical instruments to robotics. There's plenty of interaction (via video or computer activities), or in some cases plain old action, as with the many demonstrations of steam machinery. Grab a map of the museum once you're inside; you'll need it!
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Ray Hughes Gallery
Beyond the corrugated iron cows and enormous wooden fish, old-time art dealer Ray Hughes wheels and deals. The Australian and contemporary Chinese and African art he flogs is some of Sydney's classiest. Even if you don't buy a cow, his bohemian warehouse is worth a look.
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Redleaf Pool
Not really a pool at all, Redleaf is the closest swim-able beach to the city - and as such attracts an urbane collection of inner-eastern locals. A boardwalk runs around the top of a shark-net, giving it an enclosed pool-like feel. This and two floating pontoons are for those who confuse beaches with catwalks. The western end is popular with families, while the eastern is nearly exclusively colonised by gay men.
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Rocks Discovery Museum
Divided into four chronological displays - pre-1788, 1788-1820, 1820-1900 and 1900-present - this excellent new museum digs deep into the history of The Rocks and leads you on an artefact-soaked tour. Sensitive attention is given to The Rocks' original inhabitants, the Cadigal people.
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Rose Seidler House
World-famous architect Harry Seidler designed this modest house (built 1948-50) for his mother and father. It's a Modernist construction and its interior reflects the style of the time, with plenty of open spaces, a muted colour scheme and the hippest furnishing of the era. Every year the Historic Houses Trust holds a Fifties Fair (usually in August) on the grounds of the house. Only serious architecture fans or true retro buffs need visit.
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Royal Botanic Gardens
These expansive gardens are the city's favourite picnic spot, jogging route and strolling venue. Bordering Farm Cove, east of the Sydney Opera House, the enchanting gardens were established in 1816 and feature plant life from the South Pacific and around the world. They include the site of the colony's first paltry vegetable patch. Long before the convicts arrived this was an initiation ground for the Cadigal people.
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Rushcutters Bay Park
This delightful waterfront park is an ideal spot for a quiet walk or jog, surrounded by enormous Moreton Bay figs, luxury yachts and overly pampered pooches. In January, this is where you'll find the country's greatest yachties, as they prepare for the gruelling Sydney to Hobart race.
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SH Ervin Gallery
This small gallery is located in the old Fort St School (1856), close to the Sydney Observatory. It houses temporary exhibitions of Australian art, and every year it hosts the extremely popular Salon des Refusés show, for rejected Archibald and Wynne Prize contenders. Disabled access is good.
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Sherman Contemporary Art Foundation
After 21 years as a cutting-edge commercial gallery, Sherman Galleries has celebrated its coming-of-age by re-opening as a not-for-profit gallery. The focus is on temporary exhibitions of work by influential and innovative artists from Australia and the Asia-Pacific region.
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South Head
The narrow peninsula heading to the harbour's southern head is one of Sydney's most sublime spots. Best approached from Bondi, the view as Old South Head Rd leaves the sheer ocean cliffs to descend to Watsons Bay is breathtaking; all at once Sydney Harbour as far as the Bridge is laid out before you. Nestled on the harbour side, Watsons Bay was once a small fishing village, which is still evident in some of the tiny heritage cottages.
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St Andrew's Cathedral
Sporting beautiful stained glass and twin spires inspired by England's York Minster, Anglican St Andrew's is the oldest cathedral in Australia (1868). There are some ugly modifications around the front door but disabled access is good. Organ recitals are held Fridays at and a concert band performs most Wednesdays at . During term time, free 'Young Music' concerts are held at Mondays and Thursdays.
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St James' Church
St James' Church was originally designed to be a courthouse but was consecrated by the Reverend Marsden in 1824, making it the oldest remaining church in Sydney. Restored in the 1950s, it contains traditional stained glass, but also the striking modern 'creation window' in the Chapel of the Holy Spirit, as well as a choir loft of dark wood and a lovely pipe organ.
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St John's Church
Grab a pamphlet inside this lovely sandstone church (1858) for an interesting 10-minute, self-guided tour. There's a separate leaflet with information about the historic stained glass windows. This Anglican congregation runs the Rough Edges Community Centre, working with the area's many homeless.
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St Mary's Cathedral
Begun in 1868 and consecrated in 1905, St Mary's is the seat of the Catholic Archbishop of Sydney. The Gothic Revival cathedral is imposingly large (106m long); its 75m-high front spires were only completed in 2000. It's at it's most stunning when the sun streams through the many stained glass windows in the early morning and late afternoon. The crypt has an impressive terrazzo mosaic floor depicting The Creation , inspired by the Book of Kells .
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St Patrick's Church
This sandstone church (1844) was built on land donated by William Davis, an Irishman transported for his role in the uprisings of 1798. His home (on the site of the chapel-turned-café) may have been the first Catholic chapel in Australia and it was used for clandestine devotions. Look for the elaborate brass altar, spectacular stained glass windows and colourful statues.
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St Patrick's College
The college is the large building (1889) on the hill, southeast of Manly's town centre. It was a seminary for years and the first Catholic training college to be built in Australia; you can read about it in author Thomas Keneally's early works. It's now a tourism and hotel management school, and the recipient of a Unesco award for cultural heritage conservation.
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St Philip's Church
Completed in 1856 by architect Edmund Blacket in the High Victorian Gothic style, St Philip's is the successor of a line descending from Sydney's original Anglican parish church (1793). Today it's a peaceful and unobtrusive structure dwarfed by the area's surrounding skyscrapers. It's usually kept locked, but the parish workers at the neighbouring office are happy to open up the doors to visitors. A handy self-guided tour pamphlet is available.
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Star City
This large casino complex includes a major theatre, retail stores, restaurants, bars and a luxury hotel. It's located on the waterfront in Pyrmont, on the northwestern headland of Darling Harbour. The décor is best described as 'Disney-meets-Outback', complete with a lagoon bar (think indoor waterfall), fake palm trees and flashy lights all over the place.
