About this tour
Walk through Surry Hills and Darlinghurst's shadier chapters with a local historian guiding you past 20 sites tied to Sydney's 1920s–30s underworld. This 2.5-hour tour traces the rise of Tilly Devine and Kate Leigh, the ruthless women who built criminal empires in backstreet laneways, alongside their foot soldiers, dealers and hired muscle. You'll finish on Stanley Street among its speakeasy-style bars, armed with a visual folder of period maps, mugshots and archival photographs.
Highlights
- Tilly Devine and Kate Leigh's criminal dynasties in detail
- Historic laneways rarely explored by regular tourists
- 20 documented sites linked to gang activity
- Period photographs, maps and underworld figures
- Expert local historian narrating the narrative
- Stanley Street speakeasy bars to continue afterwards
What to expect
Expect a street-level narrative that doesn't sanitise the era. Your guide will point out converted sly-grog dens, safehouses and venues where violence settled disputes, weaving together stories of the women who outmanoeuvred rivals in a male-dominated criminal hierarchy. The laneways remain atmospheric—narrow, layered with history—and the walk moves at a steady pace across roughly 20 locations. You'll see how the neighbourhood's physical layout enabled the underground economy to thrive. The tour wraps on a buzzing street where you can grab a drink and reflect.
Good to know
Bring comfortable walking shoes; the terrain is uneven in places. Not suitable if you have spinal injuries, are pregnant, or need a pram. Gratuities aren't included. Food isn't provided, but your guide will suggest local spots. Public transport is nearby if you need it.
Tour sold and operated by its supplier via Viator. Descriptions on this page are original AU & NZ Travel summaries, not copied from the operator. Prices and availability are confirmed at checkout.