Sydney is one of the world’s most beautiful and liveable cities. It’s fast, glamorous, and brash. Its harbour, its bridge, and opera house are global icons.

But Sydney’s shy about its past.  

Sydney is where the long story of the dispossession of Australia’s First Peoples starts. It’s where a miserable penal colony was transformed into one of the most prosperous places in the world. It’s where the seeds of Australia’s celebrated and contested egalitarianism were first planted. It’s where multiculturalism was resisted and then embraced. 

Today, Sydney is a uniquely fascinating place — prosperous, diverse, and reckoning with the challenges of the era while wrestling with its past.  

Sydney by the Book takes a selection of books to get us started as we dive into stories of the past and present.

We’ll explore Sydney’s beautiful best in natural vistas, architecture, and art. We’ll see well known places from a different perspective and we’ll explore lesser-known angles too.

Our experience is a unique foray into Sydney and the nation that followed from its colonisation.

Old Compass Travel is a specialist in active cultural experiences. We love to read. We love to learn and share ideas. We love to walk and explore. And we enjoy a laugh.

Group size: maximum 8

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SYDNEY BY THE BOOK – ITINERARY BRIEF 2026

Day 1. Welcome brief and dinner.

Day 2. The Coast – Botany Bay, The Endeavour, Cook and Banks to South Head and Sydney Harbour. Colonisation and dispossession. Sydney Harbour National Park, lighthouses, shipwreck tales, garden estates.

Day 3. The Rocks from invasion to convict colony to booming vice-ridden port. Harbour Bridge, Opera House. Hyde Park precinct – convict architecture, politics, public spaces, art, and gardens.
Dinner – Crafted – Art Gallery of New South Wales

Day 4. Parramatta – frontier conflict – women’s history – Australia’s oldest colonial buildings – The Whitlam era.

 

SYDNEY BY THE BOOK – THE PLACES AND THEMES

Sydney’s Pacific coast – Botany Bay, South Head to Sydney Harbour

When James Cook’s Endeavour landed in Botany Bay in April 1770, neither Cook nor the local Gwaegal people could have imagined what the arrival would ultimately mean. The Gweagal got their first experience of British gunfire and the confiscation of their possessions. 18 years later, 11 ships would return, laden with convicts. British colonisation began and with it, the long dispossession of Australia’s First Peoples across the continent. Botany Bay remains an incredibly evocative place where it’s still possible to imagine those early encounters. It’s also a naturally dramatic place of rugged Pacific coast, native flora, birds, and migrating humpback whales in the distance in the cooler months.

In January 1788, soon after eight months at sea and dissatisfied with conditions at Botany Bay, Captain Arthur Phillip and a small group of his men headed north seeking a more suitable place for the convict colony. They entered Sydney Harbour, passing South Head. They spent their first night in what is now part of Sydney Harbour National Park. They were in awe of the harbour’s size, beauty, and suitability for settlement. They encountered the Gadigal and Birrabirrgal peoples.

South Head is where some of Australia’s earliest defensive facilities were built in the 1850s. In the 1820s, William Charles Wentworth acquired Vaucluse House and built a massive estate here— much of which remains.

 

The Rocks and the evolving colony — contemporary Sydney — the Bridge and Opera House — art and architecture — convicts, governance, public spaces and institutions

The Rocks is Australia’s oldest colonial neighbourhood— where a convict colony transitioned into an economic powerhouse. This is where the dispossession of Australia’s First Peoples really begins. It’s where some of the earliest language exchange with the Gadigal people occurred. By the early 1800s, The Rocks was a gritty, crime-ridden port settlement and a driver of a rapidly expanding agricultural colony. The surviving sandstone architecture of The Rocks was saved in the 1970s in Australia’s most fierce heritage battle, led by a communist union leader, Jack Mundey. 

Sydney’s magnificent twentieth-century icons, the Harbour Bridge and the Opera House, are never far from view in the harbour precinct. They represent the best of the city in ambition and values. Their creation was mired in scandal.

The Hyde Park and Macquarie St precincts bring together parks and gardens as well as convict-designed and built Sydney heritage architecture. The earliest political and legal institutions, a hospital, early churches, and a synagogue, are also located here.

The Royal Botanical Gardens, the State Library, and the Art Gallery of New South Wales celebrate Sydney’s public spaces and institutions and the evolution of the idea of Australian art.

Parramatta – frontier conflict – women’s history – Australia’s oldest colonial buildings – The Whitlam era

Parramatta was the second major British colonial settlement and is home to Australia’s oldest surviving colonial buildings.

Parramatta’s historical significance is little understood. Its successful crops stabilised the hungry early colony’s food supply. From Parramatta, agriculture developed in New South Wales. The colony’s food security and agricultural development were achieved in a land grab that accelerated the westward expansion and the dispossession of First Peoples. The Battle of Parramatta was an important early frontier confrontation and brought to prominence legendary Aboriginal fighter Pemulwuy. The infamous Parramatta Female Factory was where convict women were detained. World Heritage-listed Government House was an important base for early governors. Parramatta has a special connection with women’s history, the convict experiment, and the spawning of a homegrown aristocracy from the colonial officer elite that fought to secure special privileges in the convict colony.