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 on Stanley Street a popular street with many speakeasy style bars.
Please meet outside the **old Excelsior Hotel, El Loco at Excelsior** on 64 Foveaux Street. A short stroll from Central Station.
This tour finishes with on Crown Street, a great place with many speak-easy style bars and restaurants. Busses, Central Station and the railway are all with in walking distance of this location with connections to and from the city.
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.
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.
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Show more
You can cancel up to 24 hours in advance of the experience for a full refund.
Your guide to the flawless travel experience