Map: The Rocks and Circular Quay

For a window into Sydney’s early days and a close encounter with the Sydney Opera House and Sydney Harbour Bridge, take a stroll through The Rocks and around Circular Quay.

Start your tour at Observatory Park, where you can visit the old (1) Sydney Observatory (www.sydneyobservatory.com.au) and take in some sweeping harbor views. At the base of the hill is (2) The Garrison Church (corner of Argyle and Lower Fort Streets; www.thegarrisonchurch.org.au). Built in 1843, this is Australia’s oldest church and where Australia’s first prime minister Edmund Barton went to school. From here, wander down Argyle Street through the (3) Argyle Cut (corner of Argyle Street and Bradfield Highway), a dramatic tunnel dug through the hillside by convicts.

On the far side, head left onto Cumberland Street where you’ll find (4) BridgeClimb (5 Cumberland Street; www.bridgeclimb.com). If you’re feeling brave, take a tour over the grand arch of the Sydney Harbour Bridge. Alternatively, climb the stairs from Cumberland Street onto the bridge’s eastern footpath and visit the (5) Pylon Lookout (www.pylonlookout.com.au) in the southeastern pylon. Displays here document the bridge’s construction during the 1920s and ’30s.

Back on Argyle Street, head downhill and hang left onto Kendall Lane for the (6) Rocks Discovery Museum (2-8 Kendall Lane; www.rocksdiscoverymuseum.com). The intriguing exhibits here focus on early European artifacts and The Rocks’ original residents, the Cadigal people.

From Kendall Lane, turn right onto Mill Lane and walk towards George Street. If it’s a Saturday or Sunday, (7) The Rocks Market (www.therocksmarket.com), the city’s “premier” farmers and authentic Australian products marketplace, will be in full swing. Also here is (8) Cadman’s Cottage (110 George Street). Built in 1816, it is one of Sydney’s oldest houses. John Cadman was a shipping officer at the fledgling harbor; his house later served as a sea captain’s retirement home and police headquarters. Today it houses the Sydney Harbour National Park Information Centre.

Below Cadman’s Cottage is Sydney Cove. Navigate your way around the shoreline to (9) Circular Quay, the hub of Sydney’s public transportation system. From here, ferries, buses, and trains will take you anywhere in the “Harbour City.”

Just inland from Circular Quay is the sandstone (10) Customs House (31 Alfred Street; www.cityofsydney.nsw.gov.au/customshouse). Originally an import/export clearance hall, it’s now a library and civic center. Grab a coffee at Café Sydney on the roof, and inspect the 1:500 Sydney scale model built into the lobby floor.

Detour up Bridge Street to the (11) Museum of Sydney (southwestern corner of Bridge and Phillip Streets), an outstanding multimedia museum documenting Sydney’s places, people, and development.

Back by the harbor, wander around Circular Quay East past a lively string of (12) bars and eateries. Savor some local oysters with a cold beer, or just enjoy the photo-worthy views of the Sydney Harbour Bridge across Sydney Cove.

Finish your tour on the steps of the iconic (13) Sydney Opera House (Bennelong Point, Circular Quay East), Sydney’s architectural masterpiece and No. 1 attraction.

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