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Sydney: Gangsters, Girls and Grog Walking Tour

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Tours Culture & history Walking tours

Discover the dark and dangerous history of Sydney's past on a walking tour in Surry Hills. Explore the epicenter of the city's underworld with gangsters, gambling, drinking, and drug lords.

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  • Join a local crime historian on a walking tour uncovering Sydney's seedy past
  • Get to know Australia’s legendary female mob bosses Tilly Devine and Kate Leigh
  • Admire the chic surroundings and charming terrace houses of the former slums
  • Rewind the clock to reveal criminal empires viciously fought over by mob bosses
  • Explore the trendy suburbs of Surry Hills and Darlinghurst with a local guide


Explore the seedy side of Sydney’s underworld on a fascinating walking tour through Surry Hills and Darlinghurst. Hear stories of mob bosses, gang rivalry, and criminal empires, as you stroll the streets of the now trendy inner city suburbs. From Central Station, stroll through Surry Hills (note that this suburb’s name makes it clear there are a few slopes to contend with) towards Oxford Street and into Darlinghurst. Meet the colorful collection of working girls, gangsters, drug dealers, hit-men, and mysterious street identities such as ‘Mr. Eternity’ who once plied their hidden trades in the dank corners of ‘Razorhurst’. Your guide will passionately bring to life the most notorious periods of Sydney’s criminal history on the very streets where it once all went down. In the 1920s and 1930s, Sydney was famous for its vicious gang rivalry, streets full of working girls, cocaine addiction, and sly grog (alcohol) scene. From the labyrinth of laneways littering Surry Hills and Darlinghurst, the criminal empires of an emerging underworld began to make their mark in response to a series of local laws that almost seemed to be made to be broken. The most notorious of these criminal empires were ruled by two rival mob bosses with a difference – these bosses were women. Hailed as Queens of vice Tilly Devine and Kate Leigh had crawled their way up from obscure origins over the bodies of men to become the most powerful women in Sydney. Your small group walking tour finishes on Stanley Street in Darlinghurst outside a former Razor Gang hangout. Here you may want to stick around for a post-tour drink opportunity and chat with your fellow explorers and guide.


Walking tour Crime historian guide

Important Information

  • This tour will take place rain or shine.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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