Sydney Tours and Experiences

See what others overlook. Understand what others don't.

(4.86)

A former 19th-century hardscrabble penal settlement evolves into a 21st-century world-class city.

Sydney Private Walking Tours

Context Travel Sydney Tours

Sydney, born from the arrival of the First Fleet in 1788, has evolved from a penal colony into a bustling metropolis, its streets layered with the stories of convicts, immigrants, and the trials of history. For those curious about this transformation, our Sydney walking tours offer a window into the city's past.

Our Introduction to Sydney Tour is a comprehensive exploration of Sydney's history. This tour, led by local historians who bring depth and insight to every narration, covers the spectrum from the initial British settlement to the cosmopolitan city we see today. You'll gain an understanding of how Sydney's landscape and society have shaped each other through the help of a passionate local expert.

For those intrigued by the gritty details of Sydney's social fabric, our Rocks History Tour delves deep into the lives of the city's early inhabitants. This private tour uncovers the stories of convicts, the impact of immigrant groups, and the dramatic episodes of labor unrest and the bubonic plague. Walking through The Rocks, you'll learn about the resilience and spirit of Sydney's people, guided by experts who illuminate the past with a passion for storytelling.

Both tours provide an intimate, immersive experience where you can engage directly with Sydney's history. Join us to uncover the layers of history beneath Sydney's modern facade, guided by those who know it best.

What Context Sydney Travelers Say

(4.86) – 182 Reviews

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We had an Introduction to Sydney tour with Mark during our first trip to Australia in August 2025. Mark was extremely knowledgeable, had a lot of great stories to share, and really took us through some of the city's most important sites. It was a highlight of our trip. Thank you!

Trisha

Aug 27, 2025

Informative and engaging. Survived some grim weather too!

Fiona

Aug 1, 2025

Mark was very knowledgeable and his explanations were entertaining. One of the best Context your leaders we have had.

Park

Aug 1, 2025

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