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Slums, Slashings & Sly-grog — A History Tour of Surry Hills & Darlinghurst

Known as the ‘Chicago of the South’ Sydney in the 1920s and 1930s was famous for its vicious gang rivalry, cocaine addition, and sly-grog scene.
From this labyrinth of lanes a mass of criminal empires emerged, ruled by two mob bosses with a difference – these bosses were women. Hailed Queens of the Underworld, Tilly Devine and Kate Leigh, had crawled their way up from obscure origins over the bodies (sometimes literally) of men to become the most powerful women in Sydney, and they were not about to give up that power — especially not to each other.

Join us as we explore the lesser known laneways and secrets of Surry Hills, meet the colourful collection of working girls, gangsters and hit men who gave Sydney a bad reputation, finishing with a drink at a speakeasy style bar.

per adult from




2 hours 30 minutes


Mobile ticket

Select Date and Travellers

No tour options available.

  • What's included :
    • Alcoholic Beverages - Enjoy a unique drink at a hidden speak-easy bar after your tour. Their house special is a glass of whisky with freshly squeezed apple juice. Beer, wine and non-alcoholic drinks also available.
    What's excluded :
    • This is a typical itinerary for this product

      Stop At: Central Railway Station, Eddy Ave Haymarket, Sydney, New South Wales 2000 Australia

      Meet your guide in the Grand Concourse of Central Station — a large terminus hall constructed in the early 1900s with a giant steel frame vaulted roof. Your tour guide will introduce you to the notorious characters that preyed on naive newcomers who once arrived here on the country trains.
      You'll also learn what happened here in 1916 that helped determine Sydney's underworld over the next decades.

      Duration: 15 minutes

      Stop At: Surry Hills, Surry Hills, New South Wales

      As you walk through the history of the area you'll learn about the notorious razor gangs, illegal grog-shops, brothels, gambling joints and slums. You'll also delve into the stories of the infamous crime-lords and ladies who ruled over an empire of illegal trades scattered throughout Surry Hills streets and alleyways in the roaring inter-war years.

      Duration: 1 hour

      Stop At: Darlinghurst, Darlinghurst, New South Wales

      Darlinghurst was once the playground of Sydney's not-so-glamourous underworld Queens : Kate Leigh & Tilly Devine. You'll discover the forgotten venues of their competing sly grog & bordello empires and the cocaine-crooks, standover men, gangsters, good-timers, haunts & hide-outs that kept them at the top of the food-chain.

      Duration: 1 hour

    • Departure Point :
      Central Station Grand Concourse, Eddy Ave, Haymarket NSW 2000, Australia
      Departure Time :
      2:00 PM
      Return Detail :
      Shady Pines Saloon, 4/256 Crown St, Darlinghurst NSW 2010, Australia
      Hotel Pickup :
      • Confirmation will be received at time of booking
      • Not wheelchair accessible
      • Near public transportation
      • Not recommended for travelers with back problems
      • Not recommended for pregnant travelers
      • No heart problems or other serious medical conditions
      • Most travelers can participate
      • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
      • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
      • This tour/activity will have a maximum of 10 travelers
    • You can present either a paper or an electronic voucher for this activity.
    • For a full refund, cancel at least 24 hours in advance of the start date of the experience.



    Age Req.


    Fitness Req.


    Group Size


    Organised by Journey Walks

    Activity ID: V-48144P3

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