Sydney Travel Guide

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.

What to do in Sydney

Visit Sydney Opera House

Catch a show, a beyond the stage tour or relax with a drink at the Opera Bar.

Take in Sydney Harbour Bridge from a different angle

Drive, walk, cycle or even climb the famous "coathanger" for a giddy vision of the city. A 90-minute Rocks walking tour will give you excellent views of the bridge and the Opera House.

Explore Newtown

Arty, quirky and with restaurants representing every flavour of multicultural Sydney.

Breathe in nature at Sydney Harbour National Park

Multiple pockets of astounding natural beauty with great views of the harbour. Alternatively, head for a day tour to Ku-ring-gai National Park, just 45-minutes north of the city.

Get your surf on at Bondi Beach

Bold, brash Bondi is synonymous with Australian beach culture. If you're a beginner surfer, book a lesson to get you started.

Get out the bucket and spade at Manly Beach

A hub of watersports, with a holiday-village feel.

Join the celebration at Mardi Gras

The world's biggest celebration of LGBTQ culture.

Test the grapes at the Hunter Valley wineries

A famous wine-growing region with a plethora of culinary and cultural activities to choose from.

Enjoy a weekend getaway in the Blue Mountains

Take a weekend break in one of the dinky Deco towns of the World Heritage-listed Blue Mountains. If you're on a shorter trip, book a one-day tour.

Cruise the harbour

Sydney is at its best from the harbour; take it in cheaply on the popular Manly Ferry. Alternatively, book onto a harbour cruise.

Watch for whales

Look out for whales off the North Head shore in the June–July and August–October migration periods, or book onto a whale-watching cruise.

This page contains affiliate links. All recommendations are editorially independent.

Bars and pubs

The differences between a restaurant, bar, pub and nightclub are often blurred in Sydney, and one establishment may be a combination of all these under one roof. Sydney’s bland, pub-dominated wilderness has disappeared in the inner city and you’ll find a fashionable bar on almost every corner, offering everything from poetry readings and art classes to groovy Sun-afternoon jazz or DJ sessions.

Surry Hills and Darlinghurst are the places to go for “pop-up” bars, as well as a variety of drinking holes for all tastes. Circular Quay and King Street Wharf are more touristy, yet have harbour views that even locals still savour now and again. Not to be outdone, the traditional hotels are getting in renowned chefs and putting on food far beyond the old pub grub.

Sydney has many Art Deco pubs, a style notably seen in the tilework; we’ve included some of the best below. Opening hours vary considerably: traditional pubs and beer gardens will be open 11am–11pm or later, while more fashionable cocktail bars may not open until the evening but won’t close until 2am (perhaps 4am or later at weekends).

To get to know the scene, consider joining a craft beer tour or a pub crawl in one of the mosts fascinating areas of Sydney: The Rocks.

Legendary beer gardens

Many Sydney pubs have an outdoor drinking area, perfect for enjoying the sunny weather – the five listed , however, are outright legends.

Coogee Bay Hotel

Arden St, Coogee 02 9315 6063, coogeebayhotel.com.au. Loud, rowdy and crammed with backpackers, this enormous beer garden across from the beach is renowned in the eastern suburbs. The hotel has 6 bars in all, including a big-screen sports bar for all international sporting events. Revellers can buy jugs of beer and cook their own meat. Daily 9.30am till late.

Courthouse Hotel

Australia St, Newtown 02 9519 8273. A typical Australian pub at the front, and out the back a relaxed and inviting beer garden – a favourite local hangout. Modern pub cuisine is served. Daily 10am–midnight, Sun till 10pm.

Newport Arms Hotel

Beaconsfield St, Newport 02 9997 4900, newportarms.com.au. Famous beer-garden pub established in 1880 with a huge deck looking out over Heron Cove at Pittwater. Good for families, with a children’s play area. The bistro’s range of pasta, pizza, grills and salads complements a large wine list. Daily 10am–midnight, Sun till 10pm.

The Oaks Hotel

118 Military Rd, Neutral Bay 02 9953 5515, oakshotel.com.au. The North Shore’s most popular pub takes its name from the huge oak tree that shades the entire beer garden. Cook your own (expensive) steak, or order a gourmet pizza from the restaurant inside. Daily 10am–midnight, Thurs–Sat till 1.30am, Sun from noon.

Watsons Bay Hotel

11 Marine Parade, Watsons Bay 02 9337 5444, watsonsbayhotel.com.au. The beer garden here gives uninterrupted views across the harbour, which you can enjoy with fresh fish and chips from the renowned Doyles kitchen or a steak from the outdoor BBQ. Daily 7am–10pm.

Botany Bay

The southern suburbs of Sydney, arranged around huge Botany Bay, are seen as the heartland of red-tiled-roof suburbia, a terracotta sea spied from above as the planes land at Mascot. Clive James, the area’s most famous son, hails from Kogarah – described as a 1950s suburban wasteland in his tongue-in-cheek Unreliable Memoirs. The popular perception of Botany Bay is coloured by its proximity to an airport, a high-security prison (Long Bay), an oil refinery, a container terminal and a sewerage outlet. Yet the surprisingly clean-looking water is fringed by quiet, sandy beaches and the marshlands shelter a profusion of birdlife.

Whole areas of the waterfront, at La Perouse, with its associations with eighteenth-century French exploration, and on the Kurnell Peninsula where Captain Cook first set anchor, are designated as part of Botany Bay National Park, and large stretches on either side of the Georges River form a State Recreation Area. Brighton-Le-Sands, the busy suburban strip on the west of the bay, is a hive of bars and restaurants and is something of a focus for Sydney’s Greek community. Its long beach is also a popular spot for windsurfers and kitesurfers.

Central Business District (CBD)

From Circular Quay south as far as King Street is Sydney’s Central Business District, often referred to as the CBD, with Martin Place as its commercial nerve centre. A pedestrian mall stretching from George Street to Macquarie Street, lined with imposing banks and investment companies, Martin Place has its less serious moments at summer lunchtimes, when street performances are held at the little amphitheatre, and all year round, fruit and flower stalls add some colour. The eastern end of Martin Place emerges opposite the old civic buildings on lower Macquarie Street.

Circular Quay

At the southern end of Sydney Cove, Circular Quay is the launching pad for harbour and river ferries and sightseeing boats, the terminal for buses from the eastern and southern suburbs, and a major suburban train station to boot (some of the most fantastic views of the harbour can be seen from the above-ground station platforms).

Circular Quay itself is always bustling with commuters during the week, and with people simply out to enjoy themselves at the weekend. Restaurants, cafés and fast-food outlets line the Quay, buskers entertain the crowds, and vendors of newspapers and trinkets add to the general hubbub. The sun reflecting on the water, and its heave and splash as the ferries come and go, make for a dreamy setting – best appreciated over an expensive beer at a waterfront bar.

The inscribed bronze pavement-plaques of Writers’ Walk beneath your feet as you stroll around the Circular Quay waterfront provide an introduction to the Australian literary canon. There are short biographies of writers ranging from Miles Franklin, author of My Brilliant Career, through Peter Carey and Patrick White, to Germaine Greer, and quotable quotes on what it means to be Australian.

You could then embark on a sightseeing cruise or enjoy a ferry ride on the harbour. Staying on dry land, you’re only a short walk from most of the city-centre sights, along part of a continuous foreshore walkway beginning under the Harbour Bridge and passing through the historic area of Sydney’s first settlement, The Rocks, then extending beyond the Opera House to the Royal Botanic Gardens.

Harbour cruises

Sydney offers a wide choice of harbour cruises, almost all of them leaving from Wharf 6, Circular Quay, and the rest from Darling Harbour. While many offer a good insight into the harbour and an intimate experience of its bays and coves, the altogether much cheaper ordinary ferry rides, enjoyable cruises in themselves, are worth experiencing first. The best of these is the gorgeous thirty-minute ride to Manly, but there’s a ferry going somewhere worth checking out at almost any time of the day.

There are many different cruise options, from 3-course dinner cruises over relaxing afternoon sails on a tall ship to thrilling rides on a jet boat.

Sydney Harbour Bridge

The charismatic Sydney Harbour Bridge, northeast of Circular Quay, has straddled the channel dividing North and South Sydney since 1932; today, it makes the view from Circular Quay complete. The largest arch bridge in the world when it was built, its construction costs weren’t paid off until 1988. There’s still a toll ($4) to drive across, payable only when heading south; you can walk or cycle it for free.

Pedestrians should head up the steps to the bridge from Cumberland Street, opposite the Glenmore Hotel in The Rocks, and walk along the eastern side for fabulous views of the harbour and Opera House (cyclists keep to the western side).

Sydney Opera House

The iconic Sydney Opera House is just a short stroll from Circular Quay, by the water’s edge on Bennelong Point. It’s best seen in profile, when its high white roofs, at the same time evocative of full sails and white shells, give the building an almost ethereal quality.

“Opera House” is actually a misnomer: it’s really a performing-arts centre, one of the busiest in the world, with five performance venues inside its shells, plus restaurants, cafés and bars, and a stash of upmarket souvenir shops on the lower concourse. The building’s initial impetus, in fact, was as a home for the Sydney Symphony Orchestra, and it was designed with the huge Concert Hall, seating 2690, as the focal point; the smaller Opera Theatre (1547 seats) is used as the Sydney performance base for Opera Australia (seasons Feb–March & June–Nov) and the Australian Ballet (mid-March to May & Nov–Dec). There are three theatrical venues: the Drama Theatre, used primarily by the Sydney Theatre Company; The Playhouse, used by travelling performers; and the more intimate The Studio.

If you’re not content with gazing at the outside, guided and backstage tours are available. But of course the best way to appreciate the Opera House is to attend an evening performance. You could also eat at one of Sydney’s best restaurants, Guillaume at Bennelong, overlooking the city skyline, or take a drink at the spectacularly sited Opera Bar on the lower concourse. Good-value packages, which include tours, meals, dinner cruises, drinks and performances, can be purchased at the Opera House or via the website.

Building the Opera House

Some say the inspiration for the distinctive design of the Opera House came from the simple peeling of an orange into segments, though perhaps Danish architect Jørn Utzon’s childhood as the son of a yacht designer had something to do with their sail-like shape – he certainly envisaged a building that would appear to “float” on water. Despite its familiarity, or perhaps precisely because you already feel you know it so well, it’s quite breathtaking at first sight. Close up, you can see that the shimmering effect is created by thousands of white tiles.

The feat of structural engineering required to bring to life Utzon’s “sculpture”, which he compared to a Gothic church and a Mayan temple, made the final price tag $102 million, ten times the original estimate. Now almost universally loved and admired, it’s hard to believe quite how controversial a project this was during its long haul from plan – as a result of an international competition in the late 1950s – to completion in 1973. For sixteen years, construction was plagued by quarrels and scandal, so much so that Utzon, who won the competition in 1957, was forced to resign in 1966. Seven years and three Australian architects later, the interior, which at completion never matched Utzon’s vision, was finished: the focal Concert Hall, for instance, was designed by Peter Hall and his team.

Utzon did have a final say, however: in 1999, he was appointed as a design consultant to prepare a Statement of Design Principles for the building, which has become a permanent reference for its conservation and development. The Reception Hall has been refurbished to Utzon’s specifications and was renamed the Utzon Room in 2004. He also remodelled the western side of the structure, with a colonnade and nine new glass openings, giving previously cement-walled theatre foyers a view of the harbour. Utzon died in November 2008.

Clubs

From dark den to opulent fantasy, Sydney’s thriving club scene, attracting international DJ celebrities and impressive local talent, is likely to satisfy. A long strip of clubs stretches from Kings Cross to Oxford St and down towards Hyde Park. The scene can be pretty snobby, with door gorillas frequently vetting your style, so don your finest threads and spruce up. Along with the places listed belowhere, most of the clubs in our “Gay and lesbian” listings have a fairly mixed clientele. Admission ranges from $10 to $30; many clubs stay open until 5am or 6am on Sat and Sun mornings. There are also good clubs attached to several of the drinking spots listed previously. Mentioned here are the bigger venues or places with something unusual to offer.

Darling Harbour and around

Immediately east of the city centre lies Darling Harbour, once a grimy industrial docks area which lay moribund until the 1980s when the State Government chose to pump millions of dollars into the regeneration of this prime city real estate as part of the 1988 Bicentenary Project. The huge redevelopment scheme around Cockle Bay, which opened in 1988, included the building of the above-ground monorail – now dismantled – as well as a massive new shopping and entertainment precinct. In many ways, it’s a thoroughly stylish redevelopment of the old wharves, and Darling Harbour has plenty of attractions: an aquarium, entertainment areas, a shopping mall, an IMAX cinema, a children’s playground, gardens, and a convention and exhibition centre. However, it’s only recently that Sydneysiders themselves have embraced it. Sneered at for years by locals as tacky and touristy, it took the Cockle Bay and King Street Wharf developments on the eastern side of the waterfront – with upmarket cafés, good bars and restaurants – to finally lure them.

The eastern side of Darling Harbour blends straight into the CBD with office and apartment blocks overlooking the yacht-filled water. Across the old Pyrmont Bridge, the western side is a different matter. Push beyond the wharfside developments and you’re onto the Pyrmont–Ultimo Peninsula, an altogether older industrial quarter comprising the suburbs of Pyrmont and Ultimo that have only started to smarten up since the turn of the millennium. It still has a good way to go and there’s pleasure in just wandering around marking the changes in between visits to the Star City Casino, the Sydney Fish Market and the superb Powerhouse Museum.

The Domain

Cook and Phillip Park fills in the green gap between Hyde Park and The Domain, a much larger, plainer open space that stretches from behind the historic precinct on Macquarie Street to the waterfront, divided from the Royal Botanic Gardens by the ugly Cahill Expressway and Mrs Macquarie’s Road. In the early days of the settlement, The Domain was the governor’s private park; now it’s a popular place for a stroll or a picnic, with the Art Gallery of New South Wales, an outdoor swimming pool and Mrs Macquarie’s Chair to provide distraction. On Sundays, assorted cranks and revolutionaries assemble here for Speakers’ Corner, and every January thousands of people gather on the lawns to enjoy the free open-air concerts of the Sydney Festival.

Eating

If the way its chefs are regularly poached by restaurants overseas is any indication, Sydney has blossomed into one of the world’s great culinary capitals, offering a fantastic range of cosmopolitan restaurants, covering every imaginable cuisine. For a comprehensive guide, consider investing in Cheap Eats in Sydney or the Sydney Morning Herald Good Food Guide.

The many fascinating ethnic enclaves, representing the city’s diverse communities, serve up authentic cuisines, including Jewish on Hall St, Bondi Beach; Chinese in Haymarket and Ashfield; Turkish and Indian on Cleveland St, Surry Hills; Italian in East Sydney, Leichhardt and Haberfield; Portuguese on New Canterbury Rd, Petersham; Greek in Marrickville and Brighton-Le-Sands; and Indonesian on Anzac Parade, in Kingsford and Kensington. Much further out, reached by train, Cabramatta is very much a Little Vietnam.

Sydney's Chinatown offers great food tours for you to join or if you prefer to discover the local food scene on an alternative tour, book onto a local markets and arts tour.

The Harbour

Loftily flanking the mouth of Sydney Harbour are the rugged sandstone cliffs of North Head and South Head, providing spectacular viewing points across the calm water to the city 11km away, where the Harbour Bridge spans the sunken valley at its deepest point. The many coves, bays, points and headlands of Sydney Harbour, and their parks, bushland and swimmable beaches are rewarding to explore. However, harbour beaches are not always as clean as ocean ones, and after storms are often closed to swimmers. Finding your way by ferry is the most pleasurable method: services run to much of the North Shore and to harbourfront areas of the eastern suburbs. The eastern shores are characterized by a certain glitziness and are, fundamentally, the haunt of the nouveaux riches, while the leafy North Shore is largely the domain of Sydney’s old money. Both sides of the harbour have pockets of bushland that have been incorporated into Sydney Harbour National Park, along with several harbour islands: Cockatoo Island, the largest and easily reached via Sydney Ferries; Shark Island, a popular picnic destination; former penal site Fort Denison; and Goat Island, site of a well-preserved gunpowder-magazine complex, all visitable with the Matilda or Captain Cook cruise companies; and Clark Island and Rodd Island, reachable by private vessel only.

Rushcutters Bay Park is wonderfully set against a backdrop of the yacht- and cruiser-packed marina in the bay; the marina was revamped for the 2000 Olympics sailing competition. You can take it all in from the tables outside the very popular Rushcutters Bay Kiosk.

Walking from Elizabeth Bay to South Head

Woollahra Council (woollahra.nsw.gov.au) has brochures detailing three waterside walks: the 5.5km (3hr) Rushcutters Bay to Rose Bay harbour walk, which can then be continued with the 8km (4hr 30min) walk to Watsons Bay, and the fascinating 5km cliffside walk from Christison Park in Vaucluse (off Old South Head Rd) to Watsons Bay and South Head, with shipwreck sites, old lighthouses and military fortifications along the way.

Haymarket

The section of the city centre south from Liverpool Street down to Central Station is known as Haymarket, a lively area that’s effectively a downmarket southern extension of the CBD. Between Town Hall and Central Station, George Street shifts gear as businesspeople and shoppers give way to backpackers, who jam the area’s abundant hostels, and students from the University of Technology. It’s also a markedly East Asian area with its own distinct Chinatown, a growing Koreatown and plenty of food courts.

The short stretch between the Town Hall and Liverpool Street is for the most part teenage territory, a frenetic zone of multiscreen cinemas, pinball halls and fast-food joints, though the Metro Theatre is one of Sydney’s best live-music venues. The stretch is trouble-prone on Friday and Saturday nights when there are more pleasant places to catch a film. Things change pace at Liverpool Street, where Sydney’s Spanish Corner is gradually being taken over by Korean restaurants.

The inner east

To the east of the city centre, the adjacent districts of Kings Cross and Potts Point comprise one of the city’s major entertainment districts and a popular spot for tourists (particularly backpackers). To the north you can descend a series of steps to Woolloomooloo with its busy naval dockyards and stylish Finger Wharf. South of Kings Cross, Darlinghurst and Paddington were once rather scruffy working-class suburbs, but were gradually taken over and revamped by the young, arty and upwardly mobile.

Oxford Street runs from the city southeast through Taylor Square, the heart of gay Sydney and on through the designer shopping and art gallery areas of Darlinghurst and Paddington to old-money Woollahra and the open grasslands of Centennial Parklands.

Oxford Street marks the northern boundary of rapidly gentrifying Surry Hills. While cutting-edge galleries and bars are still filling the area’s backstreets, others are looking south to go-ahead Waterloo and even edgier Redfern.

How Woolloomooloo got its name

There are several explanations of how this area came by its sonorous Aboriginal name, perhaps the least plausible being the local story that the area’s first settler, John Palmer, found a sheep in his bathroom and exclaimed, “There’s wool on my loo!” Other possible meanings include: burial place; place of plenty; young black kangaroo; young male kangaroo; and field of blood, due to the tribal fights said to have been held in the area. The name has also been rumoured to be a mispronunciation of windmill, from one that sat on Darlinghurst ridge until the 1850s.

The inner west

West of the centre, immediately beyond Darling Harbour, the inner-city areas of Glebe and Newtown surround Sydney University, their vibrant artistic communities and cultural mix enlivened by large student populations. On a peninsula north of Glebe and west of The Rocks, Balmain is a gentrified former working-class dock area popular for its village atmosphere, while west of Glebe Leichhardt is a focus for Sydney’s Italian community.

Live music

The live-music scene in Sydney has passed its boom time, and pub venues keep closing down to make way for the dreaded poker machines. However, there are still enough venues to just barely nourish a steady stream of local, interstate and overseas acts passing through, peaking in summer with a well-established open-air festival circuit. Bands in pubs and clubs are often free, especially if you arrive early; door charge is usually from $5, with $30 the top price for smaller international acts or the latest interstate sensation. Sunday afternoon and early evening is a mellow time to catch some music, particularly jazz, around town.

Big venues

The venues for major events, with bookings direct or through Ticketek, Ticketmaster or Moshtix, are the Sydney Entertainment Centre at Haymarket near Darling Harbour (02 9320 4200); The Hordern Pavilion at Driver Avenue, Entertainment Quarter, Moore Park (02 9921 5333); the Capitol Theatre, 13 Campbell St, Haymarket (02 9320 5000); the Enmore Theatre, 130 Enmore Rd, just up from Newtown (02 9550 3666); the centrally located Metro Theatre, 624 George St (also 02 9550 3666); and the State Theatre, on Market Street in the city (13 61 00).

Outdoor music festivals

Sydney loves to party, nowhere more so than at these outdoor music festivals.

Big Day Out

Held on the Australia Day weekend (late Jan; around $185; bigdayout.com) at the Showground at Sydney Olympic Park, this is an institution and features big international names such as Pearl Jam, Arcade Fire and Blur.

Future Music Festival

This alternative music fest takes place in March at the Royal Randwick Racecourse. In the past, The Progidy and Dizzee Rascal have featured (around $200; futureentertainment.com.au).

Good Vibrations

(mid-Feb; around $100; goodvibrationsfestival.com.au). A dance/hip-hop festival held at Centennial Park.

Homebake

An open-air music festival in early December (around $100; homebake.com.au), at The Domain, with food and market stalls, rides, roving performers and a line-up of up to forty famous and underground Australian bands.

Newtown Festival

Three stages, two hundred stalls and varied live music at this event, held at the Camperdown Memorial Park on the second Sunday of November.

Mardi Gras

The year’s highlight is the Sydney Gay & Lesbian Mardi Gras (02 9568 8600, mardigras.org.au): three weeks of exhibitions, performances and other events, including the Mardi Gras Film Festival (queerscreen.com.au), showcasing the latest in queer cinema. Mardi Gras starts the second week of February, kicking off with a free Fair Day in Victoria Park, Camperdown, and culminating with a massive parade and party, usually on the first weekend of March. The first parade was held in 1978 as a gay-rights protest and today it’s the biggest celebration of gay and lesbian culture in the world. The main event is the exuberant night-time parade down Oxford Street, when up to half-a-million gays and straights jostle for the best viewing positions, before the Dykes on Bikes – traditional leaders of the parade since 1988 – roar into view. Participants devote months to the preparation of outlandish floats and outrageous costumes at Mardi Gras workshops, and even more time is devoted to the preparation of beautiful bodies in Sydney’s packed gyms. The parade begins at 7.45pm (finishing around 10.30pm), but people line the barricades along Oxford Street from mid-morning (brandishing stolen milk crates to stand on for a better view). If you can’t get to Oxford Street until late afternoon, your best chance of finding a spot is along Flinders Street near Moore Park Road, where the parade ends. Otherwise, AIDS charity The Bobby Goldsmith Foundation (bgf.org.au) has around 7000 grandstand (“Glamstand”) seats on Flinders Street, from $155 each.

The all-night dance party that follows the parade attracts up to 25,000 people and is held in several differently themed dance spaces at The Entertainment Quarter in Moore Park. You may have to plan ahead if you want to get a ticket: party tickets, from Ticketek sometimes sell out by the end of January. The Sydney Gay & Lesbian Mardi Gras Guide, available from mid-December, can be picked up from bookshops, cafés and restaurants around Oxford Street or viewed online on the Mardi Gras website.

Ocean beaches

Sydney’s beaches are among its great natural joys. The water and sand seem remarkably clean – people actually eat fish caught in the harbour – and at Long Reef, just north of Manly, you can find rock pools teeming with starfish, anemones, sea snails and crabs, and even a few shy moray eels. In recent years, whale populations have recovered to such an extent that humpback and southern right whales have been regularly sighted from the Sydney headlands in June and July on their migratory path from the Antarctic to the tropical waters of Queensland, and southern right whales even occasionally make an appearance in Sydney Harbour itself.

Topless bathing for women, while legal, is accepted on many beaches but frowned on at others, so if in doubt, do as the locals do. There are two official nudist beaches around the harbour (see the sections on South Head and Middle Harbour).

Beach safety

Don’t be lulled into a false sense of security: the beaches do have perils as well as pleasures. Some are protected by special shark nets, but they don’t keep out stingers such as bluebottles, which can suddenly swamp an entire beach; listen for loudspeaker announcements that will summon you from the water in the event of shark sightings or other dangers. Pacific currents can be very strong indeed – inexperienced swimmers and those with small children would do better sticking to the sheltered harbour beaches or sea pools at the ocean beaches. Ocean beaches are generally patrolled by surf lifesavers during the day between October and April (all year at Bondi): red and yellow flags (generally up from 6am until 6 or 7pm) indicate the safe areas to swim, avoiding dangerous rips and undertows. It’s hard not to be impressed as surfers paddle out on a seething ocean, but don’t follow them unless you’re confident you know what you’re doing. Surf schools can teach the basic skills, surfing etiquette and lingo. You can check daily surf reports on realsurf.com.

The final hazard, despite the apparent cleanliness, is pollution. Monitoring shows that it is nearly always safe to swim at all of Sydney’s beaches – except after storms, when storm water, currents and onshore breezes wash up sewage and other rubbish onto harbour beaches, making them (as signs will indicate) unsuitable for swimming and surfing. To check pollution levels, consult the Beachwatch Bulletin (1800 036 677, environment.nsw.gov.au).

Bondi Beach

Bondi Beach is synonymous with Australian beach culture, and indeed, the 1.5km-long curve of golden sand must be one of the best-known beaches in the world. It’s also the closest ocean beach to the city centre; you can take a train to Bondi Junction and then a ten-minute bus ride, or drive there in twenty minutes. Big, brash and action-packed, it’s probably not the best place for a quiet sunbathe and swim, but the sprawling sandy crescent really is spectacular. Red-tiled houses and apartment buildings crowd in to catch the view, many of them erected in the 1920s when Bondi was a working-class suburb. Although still residential, it’s long since become a popular gathering place for backpackers from around the world.

The beachfront Campbell Parade is both cosmopolitan and highly commercialized, lined with cafés and shops. For a gentler experience, explore some of the side streets, such as Hall Street, where an assortment of kosher bakeries and delis serve the area’s Jewish community, and some of Bondi’s best cafés are hidden. On Sunday, the Bondi Beach Markets, in the grounds of the primary school at Campbell Parade and Warners Avenue facing the northern end of the beach (10am–4pm), are good for fashion and jewellery, or there’s the Bondi Beach Farmers’ Markets (9am–1pm). Between Campbell Parade and the beach, Bondi Park slopes down to the promenade, and is always full of sprawling bodies.

Bondi’s surf lifesavers

Surf lifesavers are what made Bondi famous, so naturally a bronze sculpture of one is given pride of place outside the Bondi Pavilion. The surf lifesaving movement began in 1906 with the founding of the Bondi Surf Life Bathers’ Lifesaving Club in response to the drownings that accompanied the increasing popularity of swimming. From the beginning of the colony, swimming was harshly discouraged as an unsuitable bare-fleshed activity. However, by the 1890s, swimming in the ocean had become the latest fad, and a Pacific Islander introduced the concept of catching waves – or bodysurfing – that was to become an enduring national craze. Although “wowsers” (teetotal puritanical types) attempted to put a stop to it, by 1903 all-day swimming was every Sydneysider’s right.

The bronzed and muscled surf lifesavers in their distinctive red-and-yellow caps are a highly photographed, world-famous Australian image. Surf lifesavers (members of what are now called Surf Life Saving Clubs, abbreviated to SLSC) are volunteers who work the beach at weekends, so come then to watch their exploits – or look out for a surf carnival. Lifeguards, on the other hand, are employed by the council and work all week during swimming season (year-round at Bondi).

Christmas Day on Bondi

For years, backpackers and Bondi Beach on Christmas Day were synonymous. The beach was transformed into a drunken party scene, as those from colder climes lived out their fantasy of spending Christmas on the beach under a scorching sun. The behaviour and litter began getting out of control, and after riots in 1995, and a rubbish-strewn beach, the local council began strictly controlling the whole performance, with the idea of trying to keep a spirit of goodwill towards the travellers while also tempting local families back to the beach on what is regarded as a family day. Nowadays, alcohol is banned from the beach and surrounding area on Christmas Day, and police enforce the rule with on-the-spot confiscations. However, a party is organized in the Pavilion, with a bar, DJs, food and entertainment running from noon to 10pm. Up to three thousand revellers cram into the Pavilion, while thousands of others – including a greater proportion of the desired family groups – enjoy the alcohol-free beach outside. Buy tickets for the Pavilion bash at Moshtix (1300 438 849, moshtix.com.au) or Ticketek (13 28 49, ticketek.com.au).

The Manly Scenic Walkway

One of the finest harbourside walks anywhere in Sydney is the Manly Scenic Walkway (10km one way; 3–4hr; mostly flat), which follows the harbour shore inland from Manly Cove all the way west to Spit Bridge on Middle Harbour, where you can catch a bus (#180 and many others) back to Wynyard station in the city centre (20min). This wonderful walk takes you through some of the area’s more expensive neighbourhoods before heading into a section of Sydney Harbour National Park (free entry), past a number of small beaches and coves (perfect for stopping off for a dip), Aboriginal middens and some subtropical rainforest. The walk can be easily broken up into six sections with obvious exit/entry points; pick up a map from the Manly visitor centre or NPWS offices.

Walking the eastern beaches Coastal Walkway

Sydney’s eastern beaches stretch from Bondi down to Maroubra. Heading south from Bondi, you can walk right along the coast to its smaller, less brazen but very lively cousin Coogee, passing through gay-favourite Tamarama, family focused, café-cultured Bronte, narrow Clovelly and Gordons Bay, the latter with an underwater nature trail. Randwick Council has designed the “Coastal Walkway” from Clovelly to Coogee and beyond to more downmarket Maroubra, with stretches of boardwalk and interpretive boards detailing environmental features. A free guide can be picked up at visitor centres and downloaded at randwickcitytourism.com.au. It’s also possible to walk north all the way from Bondi to South Head along the cliffs.

The Rocks

The Rocks, immediately beneath the Harbour Bridge, is the heart of historic Sydney. On this rocky outcrop between Sydney Cove and Walsh Bay, Captain Arthur Phillip proclaimed the establishment of Sydney Town in 1788, the first permanent European settlement in Australia. Within decades, the area had degenerated into little more than a slum of dingy dwellings, narrow alleys and dubious taverns and brothels. In the 1830s and 1840s, merchants began building fine stone warehouses here, but as the focus for Sydney’s shipping industry moved from Circular Quay, the area fell into decline. By the 1870s and 1880s, the notorious Rocks “pushes”, gangs of “larrikins” (louts), mugged passers-by and brawled with each other: the narrow street named Suez Canal was a favourite place to hide in wait. Some say the name is a shortening of Sewers’ Canal, and indeed the area was so filthy that whole streetfronts had to be torn down in 1900 to contain an outbreak of the bubonic plague. It remained a run-down, depressed and depressing quarter until the 1970s, when there were plans to raze the historic cottages, terraces and warehouses to make way for office towers. However, due to the foresight of a radical building-workers’ union that opposed the demolition, the restored and renovated historic quarter is now one of Sydney’s major tourist attractions and, despite a passing resemblance to a historic theme park, it’s worth exploring. It’s also the best place for souvenir shopping, especially at weekends when The Rocks Market takes over the northern end of George and Playfair streets; also on Playfair Street, Rocks Walking Tours provide excellent guided tours of the area.

Shopping

Sydney’s main shopping focus is the stretch between Martin Place and the QVB in the CBD. Apart from its charming old nineteenth-century arcades and two department stores, David Jones and Myers. If you’ve run out of time to buy presents and souvenirs, don’t worry: the revamped Sydney Airport is attached to one of the biggest shopping malls in Sydney, with outlets for everything from surfwear to R.M. Williams bush outfitters, at the same prices as the downtown stores. The Rocks is the best place for souvenir and duty- and GST-free (VAT-free) shopping.