Melbourne: Gangsters, Brothels and Lolly Shops Tour

If you’re keen to uncover a side of Melbourne most visitors overlook, the Gangsters, Brothels and Lolly Shops Tour offers a fascinating glimpse into the city’s shadowy past. For just $33 per person and lasting about two hours, this guided walk takes you through the historic district of Little Lon, where women ran the streets and gangsters fought for control. Led by passionate historian Michael Shelford, the tour promises a mix of gritty storytelling, authentic sights, and vivid characters from Melbourne’s underground era circa 1850s to 1940s.

What we love about this experience is the attention to detail and the authenticity of the stories. You’ll visit the former homes of notorious figures like Squizzy Taylor, and see buildings that once served as brothels and speakeasies, places that tell tales of illicit activity and brave women. The tour also offers a visit to the last remaining single-storey cottage tucked away in Melbourne’s back lanes—a glimpse into everyday life in a bygone era.

The only consideration is that the walk involves some outdoor exploring—so comfortable shoes and weather-appropriate clothing are essential. If you’re curious about Melbourne’s less-glamorous history, especially its crime and vice scenes, and enjoy detailed storytelling, this tour is a perfect fit. It’s especially suited for history buffs, local residents, or anyone eager to see a different side of Melbourne.

Key Points

Authentic Stories: Learn about women who ran the streets and fought gangsters, offering a nuanced view of Melbourne’s past.
Historic Sites: Visit actual former brothels, opium dens, and speakeasies, bringing history to life.
Expert Guide: Michael Shelford’s deep knowledge makes complex history engaging and easy to follow.
Affordable Value: At just $33, the tour provides a detailed, well-researched experience.
Walking Experience: Expect an outdoor walk through Melbourne’s alleyways and laneways—good shoes are recommended.
Local Perspective: The tour is popular with Melburnians and visitors alike, especially those interested in true crime, social history, and urban stories.

You can check availability for your dates here:

An In-Depth Look at the Melbourne Underworld Tour

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Exploring Little Lon: An Underground Snapshot

The tour begins in downtown Melbourne at the Coopers Inn Hotel, a well-known meeting point, where the small group gathers ready for an adventure into Melbourne’s gritty past. You’ll be walking through tiny alleys and side streets, which once housed sly grog shops (illegal bars) and houses of ill-fame. The atmosphere is a mix of curiosity and respect, as Michael shares stories about women who fought against the odds to run these establishments, often in a male-dominated underworld.

What truly elevates this walking tour is how it connects past and present—many of these buildings have vanished, yet their stories remain. You get a clear sense of how the city’s social fabric was woven through vice, resilience, and rebellion.

The Story of Squizzy Taylor: Melbourne’s Most Notorious Gangster

One of the tour’s highlights is the stop outside the former home of Squizzy Taylor, a name still whispered in Melbourne’s crime history. Taylor’s reputation for shootings, bombings, and brawls makes him a compelling figure, and Michael’s recounting of his exploits is both entertaining and enlightening. You’ll learn how Taylor’s violent pursuits clashed with the women running the local brothels, who stood their ground despite threats and intimidation.

This segment offers a vivid picture of gangster rivalries and their impact on Melbourne’s streets. The stories are told with a balance of intrigue and respect for the complex characters involved.

From Opium to Cocaine: The Forbidden Flavors of the Past

Another fascinating part of the tour is the exploration of former opium dens and cocaine cafes, places where the characters of Melbourne’s underworld sought their escape or distraction. Michael’s descriptions of these clandestine establishments shed light on the social and drug culture of the era. You’ll learn about the types of people who visited these spots, from workers seeking relief to criminal figures.

The stories of brawls, shootings, and police raids that unfolded in these venues add a layer of danger and drama to the tour. As one reviewer mentions, Michael’s well-researched and thoughtful narration makes these stories both entertaining and educational.

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The Last Cottage and the Hidden Laneways

A visit to the last remaining single-storey cottage in Melbourne’s back lanes offers a rare glimpse into domestic life amid the chaos. It also serves as a reminder of how the area has transformed, with much of the original architecture lost or hidden behind modern facades.

The tour wraps up by walking through narrow laneways that once buzzed with illicit activity. These alleyways, often overlooked today, tell stories of resilience, crime, and community—testament to Melbourne’s layered history.

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The Value of the Tour: Detailed, Engaging, and Affordable

The $33 price offers excellent value considering the depth of storytelling and the authenticity of the sights. The two-hour format is perfect for a half-day adventure, giving you enough time to absorb the stories without feeling rushed. The fact that the tour is wheelchair accessible and operates in the morning or evening makes it flexible for various schedules and needs.

What the Reviews Say

It’s clear from 25 enthusiastic reviews that Michael’s expertise and passion make a significant difference. Comments like “Michael’s knowledge was amazing” and “the stories kept you fascinated the whole time” underline how well this tour resonates with visitors. Many appreciate the well-researched facts and the entertaining delivery, which makes historical figures and events come alive.

Who Is This Tour Best For?

This experience is perfect if you enjoy urban exploration, history that’s both gritty and human, or stories of crime and resilience. It suits those who appreciate a guided walk with a knowledgeable host, and who want to see Melbourne’s hidden past beyond the usual tourist spots. It’s especially appealing to history buffs, locals eager to learn more about their city, or anyone interested in true crime stories.

If you’re after colorful stories, authentic sites, and a walk through history with humor and passion, this tour will fit well into your Melbourne itinerary.

Frequently Asked Questions

How long is the tour?
It lasts approximately two hours, making it a manageable walk that fits into most half-day plans.

Where does the tour start?
The meeting point is at 282 Exhibition Street, outside the Coopers Inn Hotel. You might also spot the group in the small paved park across the lane if you’re running late.

Is this tour accessible for wheelchairs?
Yes, the tour is wheelchair accessible, though some outdoor walking over uneven surfaces might be involved.

What should I wear?
Comfortable shoes for walking are recommended, along with sunscreen or weather protection depending on the day.

Is the tour suitable for children?
The stories are mostly about adult themes—crime, vice, and street life—so it’s best suited for teenagers and older.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Are drinks or food included?
No, the tour is a walking exploration; however, nearby cafes are available for refreshments afterward.

What makes this tour different from other Melbourne walking tours?
It focuses specifically on Melbourne’s underground, criminal, and social history, with detailed stories about women in crime, gangsters, and illicit venues—a niche many tours do not cover.

How large are the groups?
While not specified, small groups are typical for this type of walking tour, ensuring a more personal experience.

Is the tour offered in languages other than English?
Currently, it is only available in English.

Final Thoughts

For travelers eager to step off the beaten path and see Melbourne through a different lens, this tour offers a compelling journey into the city’s less-glamorous but equally captivating past. The expert storytelling combined with real historic sights makes it a value-packed experience that enriches your understanding of Melbourne’s urban fabric.

If you’re fascinated by stories of crime, resilience, and women’s roles in history, and enjoy a walk through hidden alleyways and historic buildings, this tour is a clever way to spend a couple of hours. It’s ideal for those looking for authentic local stories delivered by someone who clearly loves sharing Melbourne’s colorful history.

For travelers who appreciate well-researched, engaging narratives and a small-group atmosphere, this tour ticks many boxes. It’s a chance to see Melbourne beyond the postcard, uncovering stories that still echo through its streets today.