Review: Sydney historical walking tours explore the city’s fascinating past, present and future

Sydney's colonial architecture, culture and colloquialisms blend with 21st century construction, driving historic precincts like The Rocks, Barangaroo and Darling Harbour skyward. This fascinating Sydney walking tour immerses guests in the city's history - both old and new. Review: Barry Johnson

Sydney history walking tours
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  • Rated 4.5 stars
  • 90%

  • Sydney historical walking tours with Urban Adventures
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  • Last modified: January 11, 2018

These Sydney historical walking tours explore the back story of The Rocks and harbourside precincts, while also providing a glimpse of what the future holds for the cityscape. Your local guide will reveal the stories behind many of the city’s landmarks.

Tour name: Sydney with Conviction
Runs: Daily (depending on numbers)
Departure point: Booking Centre, Wharf 6, Circular Quay
Departure time: 10am
Duration: 2.5 Hours (approx.)
Inclusions: Guided walking tour with commentary

As Captain Cook sailed past Sydney Harbour, could he have imagined that a colony of convicts would flourish here – becoming a legendary collection of characters rich and poor – and forming the foundation of modern Australia?

Urban Adventures’ Sydney historical walking tours – aptly named Sydney with Conviction – allow you to delve into the lives of these men, women and children, while exploring The Rocks, Darling Harbour and the oldest parts of the Sydney city shoreline.

Our guide Louise, dressed in a bright red t-shirt, greets us with a broad smile beside the ferry terminals at Circular Quay. Under clear autumn skies our first stop shines. The brilliant white sails of the Sydney Opera House signal a theme of stunning controversies on this tour. Many will be aware that Jørn Utzon, the bold designer of this modern wonder of the world, battled convention in vain to complete his masterpiece.

Sydney historical walking tours

Sydney historical walking tours: Sydney Opera House

Alongside the must-visit Museum of Contemporary Art and beneath the cool shadow of a giant cruise ship, Louise introduces our group to the Sydney Harbour Bridge – the icon that will reign over us throughout this tour.

The vast ‘coathanger’ of imported British steel offers the best views of the city – if you know where to go. We’re given the inside tip while we attempt impersonations of Paul Hogan – a rigger on the bridge before he built a bridge to stardom.

On the cobblestoned streets of The Rocks, haggling in the open air markets evokes visions of horse-drawn carriages, hat-wearing gentleman and ladies in petticoats. Early citizens would have visited the same discreet laneway we’re standing in to do business with the city’s first government architect – Francis Greenway – a former forger who adorned Australia’s first $10 note!

Sydney historical walking tours

Sydney historical walking tours: The Rocks. Image: Bigstock

Tucked between restaurants and pubs gearing up for lunchtime trade, the walls of the laneway are etched with the unique marks of the convicts tasked with chipping at the Sydney sandstone blocks to build tiny homes – each of which would house up to a dozen occupants.

In The Rocks Discovery Museum we hear stories of those first residents long since departed, but we’re all surprised to discover that the last convict (who was transported to Fremantle) passed away as late as the 1930s.

Sydney historical walking tours

Sydney historical walking tours

Climbing upward to Foundation Park, we watch speedboats and ferries bobbing on the harbour swells. Whaling ships, captained by Americans in search of ‘white whales’, once sailed from here as anxious wives prayed for a safe return.

Turning west we see social housing wedged between trendy terraces, overlooking former wharves and warehouses. Locals wave from balconies, some with coffees, with a cheeky few gulping icy beers. The luxury apartments at Finger Wharf seem a world away from convict hardship, with regal yachts moored at private jetties. Nicole Kidman and Keith Urban once called this home.

As we circle south along the water’s edge, the new Barangaroo Reserve extends before us like a carpet of native plants and lush lawns, lined with wooden pathways and giant sandstone blocks, claimed from the recent excavations. The hefty blocks are microchipped, preventing theft (however unlikely!) of the colourfully streaked stones from Sydney’s own pharaonic building site.

Sydney historical walking tours

Sydney historical walking tours: Barangaroo Reserve. Image: Bigstock

At the southern end of the reserve, the Barangaroo commercial development (which will include the six-star luxury Crown Sydney Casino – due to open in 2021) gleams amid a skyline dotted with cranes. It’s testament to the city’s ongoing construction boom and property prices that stretch into the stratosphere.

A choir’s angelic tones resonate from the amphitheatre constructed under the reserve, as we emerge onto Stargazer Lawn, where visitors are encouraged to look to the heavens when the sun sets. Another option is to peer through the telescopes at nearby Sydney Observatory.

Sydney historical walking tours

Sydney historical walking tours: Lord Nelson Hotel. Image: Joanne Karcz

Fittingly, these Sydney history walking tours end beside monuments to two of the early colony’s contrasting passions, religion and alcohol, which occupy opposite sides of Millers Point. One is the Garrison Church – the city’s oldest military house of worship. The other is the Lord Nelson Brewery Hotel – arguably the city’s longest-serving public house.

If you want to walk a mile with Sydney’s convicts and get a glimpse of the city’s future, you’ll be stepping in the right direction on these fascinating Sydney historical walking tours.

Barry travelled as a guest of Urban Adventures.

Additional images: Bigstock


Barry Johnson

About the writer

Barry Johnson is a freelance writer living in Sydney, but with a trail of Aussie souvenirs scattered throughout previous homes in Europe, America, Asia and the Middle East. Barry believes travelling is an adventure where the highlights push you on to the next trip and the lowlights can be laughed at with hindsight. Without a passport, he’d have missed getting lost in the Californian forest a week after the Blair Witch Project went viral, building a giant Buddha on a Cambodian mountain, camel racing in an Egyptian desert and teaching English to Peruvian children as they taught him Quechua, the language of the Incas.

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