Urban Odyssey: Secrets of Sydney's City Streets

Wander through the wonderfully weird history of Sydney’s city streets, structures and little-known laneways.

Discover hidden history, unique architecture and fascinating stories on a small group cultural experience led by a sharp-tongued Sydney historian.

Soak up the secrets of Sydney’s city-scape.

Sydney’s history is unlike any other city. Yes, that’s a big call but we invite you to come discover why. The streets, structures and sculptures that you’ll find squeezed into the CBD are soaked in strange and often sinister stories that are hidden in plain sight. On this expert-led walking tour, you’ll weave throughout time and space to uncover urban underworlds, eccentric architecture and hidden details both subtle and satisfying.

• Starting with a drink at Since I Left You

• Duration approx. 2.5 hours

• Public tours: $58 per person

About this tour

Kicking off with a complimentary drink in a hidden cobblestone courtyard at SILY bar on Kent Street, we’ll set off on a story-filled exploration of Sydney’s ever evolving city-scape and discuss its incredible transformation from ancient times to the marvellous metropolis we know today. We’ll unpack the eclectic array of industrial, opulent and at times absurd architecture that lines the busy city blocks of York, Clarence, Kent, George and Pitt Streets. From old opium dens to art deco masterpieces, this is Urban Odyssey will entertain, educate and enrichen your understanding of Sydney’s CBD.

Tour details

• Group size: this tour runs on a minimum 4 pax and a maximum 15 pax (contact us to arrange a private tour with flexible group size options).

• Start location: Since I Left You (SILY) small bar at  338 Kent Street, Sydney. Check in with the bar staff on entry to connect with your guide and get your pre-tour drink voucher.

• End location: Outside the Grace Building. Corner of King and York Street.

• Length: Over approximately 2.5 hours you’ll cover around 3 km through the city at a leisurely pace.

• Content: This tour has been carefully curated for those who love architectural insights, hidden history and urban crime stories. It is designed to engage both Sydney locals and visitors and is hosted by a professional guide-historian carrying a display folder full of historic photos, maps and paintings.

Discover the stories behind

• Town Hall

• St Andrews Cathedral

• Queen Victoria Building

• State Theatre

• Centre Point Tower

• Strand Arcade

• Pitt Street Mall

• General Post Office

• Martin Place

• And much more