Uncover the dark and intriguing history of Surry Hills and Darlinghurst, known as the ‘Chicago of the South’ in the 1920s and 1930s. Discover the stories of powerful female mob bosses, gangsters, and working girls on this immersive history tour.
-
Central Railway Station - 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. - Surry Hills - 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 - 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.
- Tour ends at Stanley Street, known for its speakeasy bars and restaurants
- 2.5 hour guided walking tour of about 20 historical sites
- Goods and Services Tax included
- Visual folder with historic photos, maps, and portraits
- Expert local historian as your guide
- Gratuities
- Food is not included on this tour, but your tour guide will have fantastic local recommendations
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.
- Not recommended for strollers
For a full refund, cancel at least 24 hours before the scheduled departure time.
