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Discover Sydney’s notorious past with a 2.5-hour walking tour through Surry Hills. Learn about legendary female mob bosses and hidden crime stories in a lively city neighborhood.
Discover Sydney’s notorious past with a 2.5-hour walking tour through Surry Hills. Learn about legendary female mob bosses and hidden crime stories in a lively city neighborhood.
Book with Journey Walks
Verified experiences and guided adventures in the surrounding area.
93 ratings
Operated by Journey Walks · Surry Hills, New South Wales
Situated in the heart of Sydney, Surry Hills is a neighborhood where history and modernity collide. Once infamous as the 'Chicago of the South,' this area has a gritty past rooted in gangland rivalries and female mob bosses like Tilly Devine and Kate Leigh. Journey Walks offers a captivating 2.5-hour walking tour that uncovers the clandestine stories behind the colorful laneways and alleys, taking visitors deep into the city’s criminal history while highlighting its lively contemporary culture. This tour isn't just about historical facts; it’s an immersive experience that paints a vivid picture of Sydney’s past, told through stories of crime, resilience, and the vibrant streets that have transformed over the decades.
As you stroll past historic buildings and hidden corners, you'll hear about the fierce rivalry between female gangsters and their influence on Sydney’s underground scene. The tour offers a rare glimpse into the city’s darker chapters—an ideal choice for travelers interested in crime history, architecture, and urban storytelling. What makes Journey Walks stand out is its ability to blend storytelling with city exploration, making history accessible and engaging.
The tour is suitable for most fitness levels, as it covers approximately 2.5 miles at a moderate pace. Wear comfortable walking shoes, and bring a sense of curiosity. Whether you’re a history buff, a local seeking new stories, or a visitor wanting a fresh perspective on Sydney, this walk provides a memorable, behind-the-scenes look at the city’s colorful past. Recognized for its engaging guides and authentic storytelling, Journey Walks has become a staple for those craving a different side of Sydney’s history.
Don’t forget your camera: the architecture and street art along the way provide fantastic photo opportunities, especially during golden hour. Book your spot through their referral link and prepare for an adventure that uncovers Sydney’s gangster roots, all from the footsteps of Surry Hills.
Yes, booking is recommended to secure your spot, especially during peak times.
Yes, children aged 12 and up tend to enjoy the stories and walking experience.
It’s a moderate walk covering around 2.5 miles with minimal steep inclines.
Currently, tours are offered in English, but special arrangements can be made for other languages.
The tour is on mostly flat city streets, but it may not be suitable for those with mobility challenges.
Tours operate rain or shine; bring rain gear or umbrellas as needed.
Journey Walks is a Sydney-based walking tour company offering immersive, story-driven tours across central Sydney neighbourhoods. The business specialises in 2.5-hour guided walks that explore local history, architecture, true crime and urban culture. Signature tours include "GANGSTERS, GIRLS & GROG IN OLD SURRY HILLS", an exploration of rival female mob bosses and Surry Hills' gritty past; "URBAN ODYSSEY: HIDDEN HISTORY, ART AND ARCHITECTURE", which begins with a complimentary drink and uncovers laneways and opulent buildings; "KINGS, QUEENS AND CLUBS OF THE CROSS", a sunset stroll through Kings Cross’ bohemian and neon heritage; "ONCE UPON A TIME & CRIME IN PADDINGTON - A TWISTED TRUE CRIME EXPLORATION", a small-group investigation of hidden pubs and secret spots; "SYDNEY’S CONVICT COLONY – A WALKING HISTORY TOUR OF THE ROCKS", led by engaging local historians through alleys, ruins and colonial stories; and special events produced in collaboration with The Historyteller Max Burns-McRuvie that combine food, drink and heritage in historic venues. Journey Walks operates with experienced local guides and historians who present well-researched, sourced narratives and prioritise guest safety and respectful heritage interpretation. Several tours are structured for small groups to enhance engagement and provenance. The company focuses on factual storytelling, site-based interpretation and accessible routes suitable for most walkers. Booking information, schedules and group options are available online; tours depart from central Sydney meeting points listed per experience. Journey Walks aims to connect visitors and residents with the layered social history of Sydney through guided walking experiences that are both educational and entertaining. Tours run year-round with weather considerations.
Book with Journey Walks