South of Sydney Harbour
Circular Quay -- This transport hub for ferries, buses, and trains is tucked between the Harbour Bridge and the Sydney Opera House. The Quay, as it’s called, is a good spot for a stroll, and its outdoor restaurants and street performers are popular. The Rocks, the Royal Botanic Gardens, the Contemporary Art Museum, and the start of the main shopping area (centered on Pitt and George sts.) are a short walk away. To get there by public transport, take a train, ferry, or city bus to Circular Quay.
The Rocks -- This small historic area, a short stroll west of Circular Quay, is packed with colonial stone buildings, intriguing back streets, boutiques, pubs, tourist stores, restaurants, and hotels. It’s the most exclusive place to stay in the city because of its beauty and its proximity to the Opera House and harbor. Shops are geared toward Sydney’s yuppies and wealthy tourists—don’t expect bargains. On weekends, a portion of George Street is blocked off for The Rocks Market, with stalls selling souvenirs and crafts. A foodies’market operates on Fridays. To reach the area on public transport, take any bus for Circular Quay or The Rocks (on George St.) or a train or ferry to Circular Quay. Check out www.therocks.com for event info.
Town Hall -- In the heart of the city, this area is home to the main department stores and two Sydney landmarks, the Town Hall and a historic shopping mall called the Queen Victoria Building (QVB). Also in this area are Sydney Tower and the boutique-style chain stores of Pitt Street Mall. Farther up George Street are movie houses, the entrance to Sydney’s Spanish district (around Liverpool St.), and Chinatown. Take any bus from Circular Quay on George Street or a train to the Town Hall stop.
Darling Harbour -- Designed as a tourist precinct, Darling Harbour features Sydney’s main convention, exhibition, and entertainment centers; a waterfront promenade; the Sydney Aquarium; an IMAX theatre; the Australian Maritime Museum; the Powerhouse Museum; the Star City casino; a food court; and plenty of shops. Nearby are the restaurants of Cockle Bay and King Street Wharf. To reach Darling Harbour by public transport, take a ferry from Circular Quay (Wharf 5) or the light rail from Central Station. It’s a short walk from Town Hall.
Kings Cross & the Suburbs Beyond -- “The Cross,”as it’s known, is the city’s red-light district—and it’s also home to some of Sydney’s best-known nightclubs and restaurants. The area has plenty of backpacker hostels, a few bars, and some upscale hotels. The main drag, Darlinghurst Road, is short but crammed with strip joints, prostitutes, drunks, and such. It’s certainly colorful. Also here are cheap Internet centers. There’s a heavy police presence and usually plenty of “ordinary”people around, but do take care. Beyond the strip clubs and glitter, the neighborhoods of Elizabeth Bay, Double Bay, and Rose Bay hug the waterfront. To get here, take a train to Kings Cross. From the next stop, Edgecliff, it’s a short walk to Double Bay and a longer one to Rose Bay along the coast.
Paddington/Oxford Street -- This central-city neighborhood, centered on trendy Oxford Street, is known for its expensive terrace houses, off-the-wall boutiques and bookshops, and restaurants, pubs, and nightclubs. It’s also the heart of Sydney’s large gay community and has a liberal scattering of gay bars and dance spots. To reach the area by public transport, take bus no. 380 or 382 from Circular Quay (on Elizabeth St.); no. 378 from Railway Square, Central Station; or no. 355, 378 or 380 from Bondi Junction. The lower end of Oxford Street is a short walk from Museum Station (take the Liverpool St. exit).
Darlinghurst -- Between grungy Kings Cross and upscale Oxford Street, this extroverted, grimy, terraced area is home to some of Sydney’s best cafes—though it’s probably not wise to wander around here at night alone. Take the train to Kings Cross and head right from the exit.
Central -- The congested, polluted crossroads around Central Station, the city’s main train station, has little to recommend it. Buses run from here to Circular Quay, and it’s a 20-minute walk to Town Hall. The Sydney Central YHA (youth hostel) is here.
Glebe -- Young professionals and students come to this central-city neighborhood for the cafes, restaurants, pubs, and shops along the main thoroughfare, Glebe Point Road. All this, plus a location 15 minutes from the city and 30 minutes from Circular Quay, makes it a good place for budget-conscious travelers. To reach Glebe, take bus no. 370, 431, 433, 439, or 470 from Circular Quay.
Bondi & the Southern Beaches -- Some of Sydney’s most glamorous surf beaches—Bondi, Bronte, and Coogee—lie along the South Pacific coast, southeast of the city center. Bondi has a wide sweep of beach (crowded in summer), some interesting restaurants and bars, plenty of attitude, and beautiful bodies—but no train station. To reach Bondi, take bus no. 333 to Bondi Beach from Circular Quay—it takes about 40 minutes. You need to buy a ticket at a newsdealer or 7-Eleven store beforehand. A Travelten bus ticket is a good option if you are staying in Bondi. Bus no. 378 from Railway Square, Central Station, goes to Bronte, and bus no. 373 travels to Coogee from Circular Quay.
Watsons Bay -- Watsons Bay is known for The Gap—a section of dramatic sea cliffs—as well as several good restaurants and a good beer garden. It’s a terrific spot to spend a sunny afternoon. To reach it, take bus no. 324 from Circular Quay. There’s limited ferry service daily from Circular Quay (Wharf 4), starting at 10:20am on weekdays, 9:30am on weekends and holidays.
North of Sydney Harbour
North Sydney -- You can see the giant smiling clown face of Luna Park from Circular Quay, but North Sydney—across the Harbour Bridge—has little in the way of tourist attractions. It’s predominantly a business area. Chatswood (take a train from Central or Wynyard station) has some good suburban-type shopping; and Milsons Point has a decent pub, the Kirribilli Hotel.
The North Shore -- Ferries and buses provide access to these wealthy neighborhoods across the Harbour Bridge. Gorgeous Balmoral Beach, Taronga Zoo, and upscale boutiques are the attractions in Mosman. Take a ferry from Circular Quay (Wharf 2) to Taronga Zoo (10 min.) and a bus to Balmoral Beach (another 10 min.).
Manly -- Half an hour from Circular Quay by ferry, Manly is famous for its ocean beach—it gives Bondi a run for its money—and scores of cheap food outlets. A privately operated fast-ferry service also runs from Circular Quay to Manly.
West of the City Center
Balmain -- A short ferry ride from Circular Quay, Balmain was once Sydney’s main shipbuilding area. In the last few decades, the area has become trendy and expensive. The neighborhood has a village feel to it, abounds with restaurants and pubs, and stages a popular Saturday market at the local church. Take bus no. 441 or 442 from Town Hall or George Street, or a ferry from Circular Quay, and then a short bus ride (or walk) up the hill to the main shopping area.