Today, Sydney is a uniquely fascinating place — wealthy, diverse, reckoning with the challenges of the era and its own quirks, while wrestling with a complicated past that’s still being uncovered.

The city has its detractors – especially among fellow Australians. In David Williamson’s play Emerald City, Sydney is described as a “sinkhole of ambition and superficiality”. It’s a critique that pops up often. But even critics like Williamson, seldom overlook Sydney’s seductive powers.

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

Join us for a deep dive into Sydney’s big stories and stunning places!

Sydney by the Book 2027 dates and prices

Dates:
April 12 – April 16 2027
May 3 – May 7 2027

Maximum 8 guests

Talk to us about private groups.

From $3490pp Paradox Sydney Hotel
From $4290pp InterContinental Sydney
From $5890pp Capella Sydney

If you have questions or to sign up for Sydney by the Book, get in touch by email at sydney@oldcompasstravel.com. We’ll get back to you with a full tour dossier.

To receive our regular updates, join a meetup or receive a call to learn more about Sydney by the Book, sign up here.

Sydney by the Book – itinerary brief 2027

Day 1. Welcome brief and dinner. 

Day 2. The Coast – Botany Bay, The Endeavour landing, Cook and Banks. First resistance from Gweagal people. South Head and Sydney Harbour and National Park, lighthouses, shipwreck tales, garden estates.

Day 3. The Rocks from invasion to convict colony to booming vice-ridden port. Early Sydney exchanges – Dawes and First Nations languages, Phillip and Bennelong. 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.

Day 5. (Morning) Cockatoo Island – convict prison – colonial shipbuilding – WWII US Navy maintenance base.  

Tour concludes after lunch.

The books of Sydney by the Book 

We’ve curated a selection of books to provide context, shared perspective, and food for discussion for our Sydney by the Book experience. Read one, two, or dive into them all in preparation for your tour. Once you start, you’ll be captivated. We’ll read—and travel—beyond these pages too.

If you only have time for two books, we recommend starting with Leviathan and The Fatal Shore. If fiction is your thing, you may prefer following Kate Grenville’s writing.

Leviathan: The Unauthorised Biography of Sydney — John Birmingham (1999)

Birmingham went head-to-head with Sydney’s pre-Olympic hype when he published his gritty, subterranean portrait of the city in the late 1990s. Decades on, his award-winning, unorthodox history remains in print—testament to the enduring bite of his observations.

The Fatal Shore — Robert Hughes (1986)

Hughes’s epic blockbuster remains one of the few Australian history books to achieve massive, sustained global acclaim across four decades. Of course it has its detractors – especially here in Sydney. The Sydney-born art critic charts the brutal realities of convict transportation, beginning with the upheaval of late 18th-century Britain.

Dancing with Strangers — Inga Clendinnen (2003)

Anthropologist and historian Inga Clendinnen examines the earliest encounters between Sydney’s First Peoples and British colonists, reading between the lines of early colonial diaries. Her subtle, award-winning work sparked intense debate upon publication and continues to stoke debate.

The Shortest History of Australia — Mark McKenna (2025)

Fresh, sharp, and concise, McKenna’s book reframes Australian history through a contemporary lens – from one of the country’s foremost historians.

The Great Australian Silence — W.E.H. Stanner (1968)

Stanner’s landmark 1968 Boyer Lectures coined a phrase and diagnosed Australia’s historical blind spot: the structural erasure of Indigenous presence and experience from the national story. Decades later, its moral clarity holds true. The lecture is included in W.E.H. Stanner selected writings – widely available. There are other important pieces in this collection from a truly unique Australian.

The Secret River — Kate Grenville (2005)

An evocative novel tracing a pardoned convict’s claim to land along the Hawkesbury River. Loosely based on the life of her convict ancestor,  Grenville lays bare the moral cost and violent displacement at the heart of Australia’s colonial settlement.

(Also recommended: Grenville’s non-fiction companion works, Searching for The Secret River and Unsettled)

 

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 Gweagal 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 evocative place where it’s still possible to imagine those early encounters. It’s also a naturally rugged slice of Pacific coast with 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, Arthur Phillip and a small group of his men headed north seeking a more suitable place for the convict colony. Passing South Head, they entered Sydney Harbour. 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 Birrabirrigal peoples.

In the 1820s, William Charles Wentworth acquired nearby Vaucluse House and built a massive estate — much of which remains.

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 local Gadigal people occurred. By the early 1800s, The Rocks was a gritty, crime-ridden port settlement and the 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 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 all 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-recognised. Its successful crops stabilised the hungry early colony’s food supply. From Parramatta, agriculture developed. 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. Convict women were detained at the infamous Parramatta Female Factory. World Heritage listed Old 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.

ABOUT YOUR TOUR LEADER?

Since 2020, Mark has been based in Sydney and taking a fresh look at his hometown. Sydney by the Book brings those years of research and exploration together.

To find out more about Mark, check www.rustycompass.com or The Rusty Compass  YouTube channel here.

HOW WE TRAVEL

Our groups are small – maximum 8 travellers. This gives us flexibility, mobility and allows us to engage with the city in a less imposing way. Single travellers are welcome.

We spend as much time as possible on foot. It’s the best way to experience a place. We’ve designed the tour for walking. Expect to spend 2 – 4 hours walking most days at a leisurely pace. 

To travel distances we use public transport where possible – it’s part of the Sydney experience. Where necessary we use comfortable private transport. 

We stay in well located, tasteful, four and five star hotels – all with a connection to Sydney’s past.

OUR TRAVELLERS

You’ll be a curious, energetic traveller with an interest in history, culture, architecture, natural landscapes, books and more. The tour is designed for local and international travellers. You’re the kind of person who likes to do some reading when you travel. You’ll enjoy walking and exploring fresh angles. You’ll like the concept of a travelling book club.

WHAT’S INCLUDED

What’s included?
* All accommodation in well located 4 – 5 star hotels
* All breakfasts
* Some dinners – fancy and local / pub style
* All admission fees
* Mark Bowyer leads the tours 
* Special touches – talks and meetups with historians and authors.

What’s not included?
* Arrival and departure transfers.
* Travel insurance (mandatory for all tour participants – this is a requirement for final tour registration).

PUT TOGETHER YOUR OWN GROUP

You can put your own tour group together. We can also tailor a walk to your interests. Special discounts apply to private tours of more than 5.

TOURS FOR HIGH SCHOOLS AND UNIVERSITIES

Our experiences are highly educational. Ask about a special tours for senior high schools or universities.

RESERVE YOUR PLACE