Convicts and Criminals Motorbike Tour

Hard labour. Harder characters. Stories of crime and punishment.

Take a tour through Sydney’s dark past and meet the convicts, smugglers, slavers, gangsters, and criminals who left their mark on the city’s streets, buildings, shadows, and psyche. Ride with us to uncover Sydney’s murky past, where crime and rough justice were inflicted with fists, swords, muskets, razor blades, and bottles. We’ll show you the scars of Sydney’s wildest days, from the brutal convict settlement in The Rocks, to the dodgy dealings, sly grog, and violent turf wars of the 1920s and ‘30s.

Duration: 90 minutes

Highlights:

  • The Rocks – convicts and soldiers (Argyle Cut, Harrington St, Nurses Walk)

  • Justice and Police Museum

  • Rum Rebellion (Museum of Sydney)

  • Hyde Park Barracks

  • Mrs Macquarie’s Chair – Pinchgut Island

  • Darlinghurst Gaol – final justice

  • Razorhurst – sly grog and gangs in the 1920s and ‘30s

  • Kings Cross – Blood Alley/Tilly Devine (Kellett St)

  • Woolloomooloo Finger Wharf – smugglers, illegal gambling, and brothels

  • Old Fitzroy Hotel – Tradesman’s Arms stabbings

  • Frog Hollow – the slums of Surry Hills

Sydney Harbour Bridge at sunset with city skyline and harbor
Three people riding a motorcycle with a sidecar, wearing helmets, near a waterfront park with a city skyline in the background.
Aerial view of a city skyline with modern skyscrapers, a harbor, and a tower, under a partly cloudy sky.
Aerial view of Sydney, featuring the Opera House, Harbour Bridge, and city skyline with boats in the harbor.