Sydney's best guided walking tours

First published on 9 Apr 2010. Updated on 6 Jan 2011.

Golden Mile Walking Tour of Sydney's Underbelly

Best for: TV junkies and true crime buffs

Start: Under the Coke sign, Cnr William St & Darlinghurst Rd
Finish:Sugar Mill Hotel 37 Darlinghurst Rd, Kings Cross 2011
Duration: 1.5 hours
Length: 2km
When: Mon-Fri 6pm; Sat & Sun 2pm
Cost: $39
Where to refuel:Guzman y GomezCnr Bayswater Rd & Pennys Ln, Kings Cross 2011

Love the Underbelly series? Get a real-life tour of the new season's crime scene - the Golden Mile in Kings Cross. The tour offers a peek into the murky history of the Cross and a glimpse inside the clubs themselves. By the end of the tour you should know all the secrets of Sydney's infamous neighbourhood: such as how John Ibrahim got his title, ‘King of the Cross'; which Kings Cross character used to wear a lead-lined glove; and where the action is happening today. Top it all off with a free drink, and you're ready to start your big night out.

Rock and Roll Walk of Fame and Shame: Oxford Street

Best for: Music tragics

Start: Whitlam Square, Oxford St, Darlinghurst
Finish: Paddington Town Hall, Cnr Oatley Rd & Oxford St
Duration: 1-2 hours
Length: About 1.5km
When: Up to you
Cost: Free
Where to refuel: The Falconer31 Oxford St, Darlinghurst 2010

Discover the cradle of Australian rock'n'roll on this self-guided City of Sydney tour up Oxford Street. Download the podcast from the website and set out on a stroll that includes historic music venues such as French's Tavern, where Midnight Oil played early gigs, and Beatle Village, where raucous 60s bands like the Easybeats and the Missing Links went ape back in their glory days. The podcast features interviews with musicians and commentators, letting you in on their memories of Oxford Street at its wildest. The City of Sydney offers a second rock'n'roll podcast tour down King Street and Enmore Road in Newtown, as well as ten other historic walking tours in locales including Glebe, the Pyrmont-Ultimo peninsula, and Millers Point and the Rocks.

Sydney East Art Walk

Best for: Jaded office workers

Start:Art Gallery of New South Wales
Finish: Martin Place
Duration: 3 hours
Length: About 3.5km
When: Flexible
Cost: $55
Where to refuel:Café Courtyard MLC Centre, Martin Place 2000.

Ever walked past a street sculpture and wondered, what the hell is that? Now you can find out, with public art expert Gordon Elliott's five different guided tours of Sydney's public sculptures for two to ten walkers. Our pick is the Sydney East Art Walk, which covers 40 different pieces and takes you through the Botanic Gardens, past the Opera House and then through the east side of the city to Martin Place. Highlights include Kan Yasuda's monumental ‘Touchstones' outside Macquarie Place (made from the same Italian marble as Michelangelo's ‘David') and Nigel Helyer's stainless steel and sound work ‘Dual Nature' near Boy Charlton Pool. "People who've done the tour say they're more aware of their surrounds now," Elliott says.

The Rocks Ghost Tours

Best for: History buffs

Start: Cadman's Cottage
Finish: Lower Fort Street
Duration: 2 hours
Length: About 1km
When: Daily 6.45pm (Apr-Sep)
Cost: Adults $38; teens $27.
Where to refuel:Guylian Belgian Chocolate Café91 George St, The Rocks 2000

The Rocks: historic, spooky... haunted? Commence at Cadman's Cottage, on the corner of George and Argyle streets, where two convicts were allegedly hacked to pieces and then had their remains thrown into the harbour in sacks. Then towards Albert and Lower Fort Streets, where you're given a lantern to light your way along cobblestone lanes and alleyways. En route, hear about Mrs Greenfield, who, according to tour director Anne, "cut off her husband's whatever." Enter the closed doors and locked gates previously restricted to public access and witness the gruesome history of the Rocks precinct.

Sydney Opera House Backstage Tour

Best for: The smell of greasepaint

Start: Stage door
Finish: Front entrance
Duration: 2 hours
Length: 1km
When: Daily 7am
Cost: $150
Where to refuel: The tour concludes with a breakfast in the Opera House Green Room

This early morning tour takes you into the rabbit warren of hidden rooms and corridors of JØrn Utzon's world-famous building. Explore the massive dock where the opera sets are stored; inspect the orchestra pit; visit a dressing room; and stand on the stage of the Concert Hall. See the lip marks on the wall where superstitious performers like Dame Joan Sutherland and Michael Bublé have paid homage before stepping onstage. Because there's a maximum of eight on each tour, you are sure to get all of your questions answered, and a full breakfast is included in the ticket price.

CHIC in the City Fashion Walking Tour

Best for: Fashionistas

Start: Oxford St, Paddington
Finish: Various locations, Woollahra
Duration: 3 hours
When: Tue, Thu & Sat 10.15am
Length: Variable
Cost: $190 (one person); $95 (two to eight people)
Where to refuel:Quaife's Restaurant at the Hughenden Hotel14 Queen St, Woollahra 2025

Whether you deck yourself in designer gear, or view shoes as a twice-a-lifetime investment, CHIC in the City's stylist-led walking tour will bring out the material girl in anyone. Get acquainted with the exclusive boutiques of the picturesque Woollahra and Paddington neighbourhoods. Get showered in personalised fashion advice as you walk, and if you happen upon a must-have (or five), tour members get store discounts! You can customise your own tours, you'll get a complimentary gift bag of beauty samples, and champagne is included - need we say more? CHIC in the City also offers chauffeured shopping tours if you're in the mood to really splurge.

Inner West Graffitti Tour

Best for: Hipsters

Start:Oh Really Gallery, 55 Enmore Rd, Newtown
Finish: The Hub, opposite Newtown Station
Duration: 2.5 hours
Length: About 3 kms
When: By appointment; generally Sunday mornings
Cost: $12
Where to refuel:Platform 8 Bistro, Town Hall Hotel 326 King St, Newtown 2042

Veteran street artist Chris Tamm runs walking tours through the backstreets of Newtown and Enmore in order to open our eyes to the treasures they shelter. We're not talking tagging, but the extraordinary, elaborate spray-painted designs on walls and disused warehouses. The magnitude of paste-ups, political messages, stencils, and other pieces will open your eyes to just how prolific Sydney's street artists are. Tamm keeps his flock to the backstreets to avoid pedestrian traffic, which makes the whole experience a bohemian adventure in the shady lanes of wonderland.

Nick Dent, Emily Lloyd-Tait, Christy LaPlant, Erin McNulty, Daniel Nour