The Aussie city par excellence, Sydney stands head and shoulders above any other in Australia. Taken together with its surrounds, it’s in many ways a microcosm of the country as a whole – if only in its ability to defy your expectations and prejudices as often as it confirms them. A thrusting, high-rise business centre, a high-profile gay community, a clutch of fascinating museums and some vibrant art galleries, and inner-city deprivation of unexpected harshness are as much part of the scene as the beaches, the bodies and the sparkling harbour. Its sophistication, cosmopolitan population and exuberant nightlife are a long way from the Outback, and yet Sydney has the highest Aboriginal population of any Australian city, and bushfires are an annual threat.

It might seem surprising that Sydney is not Australia’s capital: the creation of Canberra in 1927 – intended to stem the intense rivalry between Sydney and Melbourne – has not affected the view of many Sydneysiders that their city remains the country’s true capital, and certainly in many ways it feels like it. The city has a tangible sense of history: the old stone walls and well-worn steps in the backstreets around The Rocks are an evocative reminder that Sydney has more than two hundred years of white history behind it.

You’ll need at least five days in this unique city to ensure you see not only its glorious harbourside but also its wider treasures. Delving into the surrounding inner-city areas of Paddington, Surry Hills and Glebe reveal more of the Sydney psyche, and no trip to the city would be complete without at least one visit to the eastern-suburb beaches – for a true taste of Sydney, take an afternoon stroll along the coastal path that stretches from Bondi to Coogee.

The area around – everything in this chapter is within day-trip distance – offers a taste of virtually everything you’ll find in the rest of the country, with the exception of desert. There are magnificent national parks – Ku-ring-gai Chase and Royal being the best known – and native wildlife within an hour’s drive from the centre of town; while further north stretch endless ocean beaches, great for surfers, and more enclosed waters for safer swimming and sailing. Inland, the gorgeous Blue Mountains – UNESCO World Heritage-listed – offer isolated bushwalking and scenic viewpoints. On the way are historic colonial towns that were among the earliest foundations in the country – Sydney itself, of course, was the very first. The commercial and industrial heart of the state of New South Wales, especially the central coastal region, is bordered by Wollongong in the south and much more enticing Newcastle in the north. Both were synonymous with coal and steel, but the smokestack industries that supported them for decades are now in severe decline. This is far from an industrial wasteland, though: the heart of the coal-mining country is the Hunter Valley, northwest of Newcastle, but to visit it you’d never guess, because this is also Australia’s oldest, and arguably its best-known, wine-growing region, where you can not only sample the fine wines but enjoy some of the best food in the state.

Brief history

The city of Sydney was founded as a penal colony, amid brutality, deprivation and despair. In January 1788, the First Fleet, carrying over a thousand people, 736 of them convicts, arrived at Botany Bay expecting the “fine meadows” that Captain James Cook had described eight years earlier. In fact, what greeted them was mostly swamp, scrub and sand dunes. An unsuccessful scouting expedition prompted Commander Arthur Phillip to move the fleet a few kilometres north, to the well-wooded Port Jackson, where a stream of fresh water was found. This settlement was named Sydney Cove after Viscount Sydney, then Secretary of State in Great Britain.

In the first three years of settlement, the new colony nearly starved to death several times; the land around Sydney Cove proved to be barren. When supply ships did arrive, they inevitably came with hundreds more convicts to further burden the colony. It was not until 1790, when land was successfully farmed further west at Parramatta, that the hunger began to abate. Measure this suffering, however, with that of the original occupants, the Eora Aborigines: their land had been invaded, their people virtually wiped out by smallpox, and now they were stricken by hunger as the settlers shot at their game. Under the leadership of Pemulwuy, a skilled Aboriginal warrior, the Eora commenced a guerilla war against the colony for much of the 1790s. However, the numbers and firepower of the settlers proved too great, and in 1802 Pemulwuy was captured and killed, his severed head sent back to England. After this, the Eora’s resistance soon ended.

By the early 1800s, Sydney had become a stable colony and busy trading post. Army officers, exploiting their access to free land and cheap labour, became rich farm-owners and virtually established a currency based on rum. The military, known as the New South Wales Corps (or more familiarly as “the rum corps”), became the supreme political force in 1809, even overthrowing the governor (mutiny-plagued Captain Bligh himself). This was the last straw for the government back home, and the rebellious officers were finally brought to heel when the reformist Governor Lachlan Macquarie arrived from England with forces of his own. He liberalized conditions, supported the prisoners’ right to become citizens after they had served their time, and appointed several to public offices.

By the 1840s, the transportation of convicts to New South Wales had ended, the explorers Lawson and Blaxland had found a way through the Blue Mountains to the Western Plains, and gold had been struck in Bathurst. The population soared as free settlers arrived in ever-increasing numbers. In the Victorian era, Sydney’s population became even more starkly divided into the haves and the have-nots: while the poor lived in slums where disease, crime, prostitution and alcoholism were rife, the genteel classes – self-consciously replicating life in the mother country – took tea on their verandas and erected grandiloquent monuments such as the Town Hall, the Strand Arcade and the Queen Victoria Building in homage to English architecture of the time. An outbreak of the plague in The Rocks at the beginning of the twentieth century made wholesale slum clearances inevitable, and with the demolitions came a change in attitudes. Strict new vice laws meant the end of the bad old days of backstreet knifings, drunk-filled taverns and makeshift brothels.

Over the next few decades, Sydney settled into comfortable suburban living. The metropolis sprawled westwards, creating a flat, unremarkable city with no real centre, an appropriate symbol for the era of shorts and knee socks and the stereotypical, BBQ-loving Bruce and Sheila – an international image that still plagues Australians. Sydney has come a long way since the parochialism of the 1950s, however, and today, Sydney’s citizens don’t look inwards – and they certainly don’t look towards England. Thousands of immigrants from around the globe have given Sydney a truly cosmopolitan air, and it’s a city as thrilling and alive as any.

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