All killer and no filler on Sydney’s crime tours

By Jay Chabon

True crime might be a morbid indulgence for some but it’s an illuminating window into the culture and history of places too.

In Sydney, a number of tour operators who specialise in educating tourists about the most heinous things the most heinous people have done in the city, recognise this.

Follow engrossing tour guides to special alleys, nooks and drags around Sydney and immerse yourself in tales of the razor-gangers, pimps and sly grog merchants who have all played a part in shaping the historical character of Sydney, for better or worse.

When you stay at Song Hotel, you can book into a number of crime tours for an absolute steal – dare we say such.

Here are some of the best.

The Coke Sign
The Coke sign is an iconic symbol of nocturnal life in Kings Cross. Photo: Newtown Graffiti

Kings Cross Crime and Passion

In all its blinking redness, Kings Cross’s Coke billboard sets the tone perfectly as meeting point for Urban Adventures’ Kings Cross Crime and Passion tour.

Kings Cross Crime and Passion is a family-friendly walking adventure that snakes to a series of locations that best represent how the Cross achieved its former infamy.

Urban Adventures, who enhances tourists’ sense of connectedness to the city by framing its tours with a local’s eye, offers intriguing commentary about how an ensemble of seedy urban scarecrows entered Sydney folklore by transforming the Cross into a cauldron of red-lit bohemia.

The tour wraps with a complimentary drink at a local bar. By then, you’ll be versed enough in the Cross’s criminal record to debrief with the group about how you see the streets in a whole new streak of neon.

A metal staircase at The Rocks
A metal staircase at The Rocks. Photo: Mike Young

Sydney Convict Colony The Rocks

What better place for stories of true crime than the sandstone cliffs of Australia’s first colonial settlement?

Many convicts made a fair go of settling in Australia in the 18th and 19th centuries but drunkenness, theft, prostitution and unsanitary street life were all prominent in the community at the time.

Journey Walks shows you how profoundly Sydney’s convict history is embedded in the sterilised facade of The Rocks as we know it today.

It’s comprehensive 2.5 hour tour takes in everything from Customs House to First Fleet relics to hidden laneways.

Listen to your history expert tell you about street gangs that hid out in the Rocks, the rum trade and the mishaps of the First Fleet as you enjoy the picturesque allure of the natural setting along the way.

Darlinghurst Gaol
Entrance gates to Darlinghurst Gaol. Photo: State records NSW

Darlinghurst Gaol Tours

The old Darlinghurst Gaol isn’t what it once was. The inmates left about 100 years ago and the arts students that attend the National Art School today are arguably much less feral.

But the old Gaol still has a vibe. In many ways, not much has really changed. It’s still a behemoth of convict-made sandstone architecture.

Twice a month, the National Art School stages Gaol tours under the lead of an expert historical guide who knows where the dark nooks and crannies are and exactly what happened in them.

In the hour it takes to get a feel for the lives the inmates lived, you’ll see the cell block theatre, the Chapel, the old Governor’s quarters, the morgue, the flogging wall, hidden tunnels and the site of the old gallows.

Some people say the place is haunted by the 76 prisoners hanged between 1841-1907. Maybe it is. But if not, given all that criminal heritage, it’s eerie all the same.

Dark Stories
Newcastle has its share of dark secrets

Dark Stories

This popular walking tour requires a road trip to Newcastle but all that transit is worth it – and part of the fun.

Dark Stories is a true crime tour featuring the entertainment that only, well, entertainers, can deliver.

Your affable tour hosts (all true crime fans) combine backgrounds in acting, singing, dancing, philosophy and research to deliver a 90-minute package characterised by good story-telling, lively performance and meticulously detailed research.

As you enjoy the scenic streets and sites of Newcastle, you’ll hear obscure true crime tales from the 1830s-1950s that unfolded right where you stand.

Fraudsters, murderers and adulterers are just some of the unsavoury nasties that Newcastle can thank for its dark past.

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