Central Business District

Sydney’s narrow, twisting streets, based on the random paths created by convicts and soldiers, are a rare reminder of the colony’s early days. Today’s CBD is dominated by soaring buildings, punctuated by a few surviving Victorian beauties and the green expanse of Hyde Park. New skyscrapers continue to be unfurled, the latest a batch of massive residential towers. Their presence has brought at least one benefit, with an influx of restaurants, bars and clubs livening up the city immensely.

Macquarie Street

Sydney’s single most historic stretch of road starts at the Opera House and runs past the Royal Botanic Gardens all the way to Hyde Park. The ­corner where the Cahill Expressway ramp meets the Royal Botanic Gardens offers a snapshot of three very ­different faces of Sydney. On one corner is the solid respect­ability of the State Library; opposite lies a row of elegant 1920s art deco apartment buildings; and on the third corner stands Sydney’s latest architectural trophy, Renzo Piano’s Aurora Place, a celebration of Sydney’s emergence as a global city. 

Heading south from here you pass the city’s most impressive stretch of heritage buildings, including the old Mint, Parliament House, Sydney Hospital (originally known as the Rum Hospital because its construction was funded by the revenue from the government’s rum monopoly) and Hyde Park Barracks. The latter dates back to 1817 and was designed by convict Francis Greenway in 1817 to house male convicts. It now ­contains a museum.

Hyde Park and the Shopping District

At the far end of Macquarie Street is Hyde Park, the CBD's main green space, which contains the exuberant Archibald Fountain and the art deco Anzac Memorial. 

Opposite Hyde Park, on the corner of Elizabeth and Market streets, the discreet glamour of Sydney’s premier department store, David Jones, marks the beginning of the city’s principal shopping precinct. Arrayed chiefly along Market and Pitt streets, particularly Pitt street Mall, you will find outlets including a second David Jones store, Myer Department Store, and ­Centrepoint shopping centre, which lies at the foot of the AMP Tower. 

Also on Market Street is one of Sydney’s most beautiful relics, the State Theatre. Acclaimed at its opening in 1929 as the greatest theatre in the British Empire, its ornate interiors, including the second-largest cut-­crystal chandelier in the world, have been beautifully preserved. 

George Street

The Strand Arcade, a beautiful Victorian arcade leading from Pitt Street Mall to George Street, is the address favoured by some of the country’s best designers, with the likes of Alannah Hill, Bettina Liano and Zimmermann all on the second floor.

Emerging on George Street, you are facing the Queen Victoria Building or QVB, a Victorian landmark designed to resemble a Byzantine palace, complete with enormous stained glass windows. Four storeys high and covering the entire block between Market and Druitt streets, it is a shoppers’ delight. At the Druitt Street end it opens onto the equally grand Victorian Town Hall.

Martin Place

From the Town Hall, head back north along George Street to Martin Place, the city’s largest pedestrian plaza. Stretching all the way to Macquarie Street, it is lined with corporate headquarters, as well as upmarket bars such as Wine Banq and shops like Paspaley Pearls headquarters. 

Martin Place’s crowning glory is the General Post Office (GPO). This was once Sydney’s most imposing building, with sumptuous interiors, a grand colonnade and an ornate clock tower. However, the tower was removed during World War II to prevent Japanese bombers using it as a navigation aid during raids (which never came) and not replaced until the 1960s. After decades of neglect, the GPO was refurbished as part of the Westin Hotel complex.