Cockatoo Island, 1839

During the 60,000 years prior to European settlement, Cockatoo Island / Wareamah was a central meeting place for Sydney’s First Peoples. The island connects to the waterways and homelands of the Wallumedegal, Wangal, Cammeraygal and Gadigal Peoples, who refer to Cockatoo Island as Wareamah. The island also features atmospheric sandstone ruins from when it operated as a convict gaol. In 2010, Cockatoo Island’s Convict Site was placed on the UNESCO World Heritage List as one of the best surviving examples nationally of convict transportation and forced labour.

In 1839, the island became a penal establishment – and for the convicts sent here, life on the island was harsh. They lived and worked under brutal conditions. During the gaol’s 30 years of operation, convicts quarried sandstone on site, and constructed the prison quarters, mess hall, guardhouse, and Fitzroy Dock (c. 1857) – the only surviving example of a dry dock built by convicts. They also constructed the underground grain silos, Biloela House (c. 1841), and a set of solitary confinement cells discovered during an archaeological dig in 2009. When viewing these notorious cells, it’s not hard to imagine the grim reality of convict life on the island.

Between 1857 and 1991, Cockatoo Island’s dockyard was a large contributor to Australia’s shipbuilding industry. A walk through the Docks, Ship Design, and Industrial precincts provides a rich sense of the island’s maritime history. During both World Wars, dock workers supported the Allied powers, and during the second World War the island acted as the main ship repairing facility in the South West Pacific.

Cockatoo Island was also home an industrial school and reformatory for girls from 1871. Repurposing the prison buildings, the reformatory housed neglected and orphaned girls, as well as girls who had broken the law. Sadly, living conditions were poor, and the girls faced harsh punishment. The Biloela Reformatory School closed in 1880.

Nestled within landscaped gardens, the island’s holiday houses and apartments offer accommodation for couples, families, and larger groups – and each dwelling pairs authentic heritage charm with modern comforts.

The Heritage Holiday Houses are an impressive sight as you reach the upper part of the island. Surrounded by lush greenery and completed circa 1915-16 in the Federation style, these symmetrical semi-detached, two-storey brick houses were first home to the island’s Medical Officer, Dr Thomas William Francis and the Engineering Manager, Mr. Jack Payne. Each house has four bedrooms that sleep up to 12 guests.

Both houses have been carefully restored, with beautiful period details including original windows and doors, ornate fireplace surrounds, high ceilings with decorative plasterwork, warm timber floorboards, and a grand central staircase. Each house also has a fully-equipped kitchen and formal dining area, light-filled modern bathrooms, and spacious lounge with flat screen TV and Bluetooth.

Outside, there’s plenty of space to relax, with a BBQ and outdoor seating area on the lawn, overlooking the harbour. And from the upstairs verandah, sit back with a glass of wine and take in magical views across to Hunters Hill.

The Harbour View Apartments were once occupied by the island’s dockyard launch driver and coxswain. Choose from three apartments – the 1 bedroom apartment is ideal for couples, and there are two 2-bedroom apartments for groups including families, both capable of sleeping up to 5 guests. Each apartment has light and airy bedrooms with high ceilings, cast iron fireplaces, polished floors, and stylish contemporary bathrooms.

Apartment have their own large entertaining balcony that capture incredible views of Sydney Harbour – the perfect spot to enjoy coffee each morning, watching the harbour come to life. And at night, the glittering city skyline is the perfect backdrop for a romantic dinner.

The Garden Riverview Apartment sleeps up to four guests in two bedrooms, and boasts views of Woolwich and Hunters Hill framed by jacaranda trees. Built in 1916, this welcoming home-away-from-home features warm timber floors, soaring ceilings, and original fireplaces, with both king and queen bedrooms simply and elegantly furnished. The bright, spacious open plan living/dining area has a large comfortable sofa and flat screen TV, making it the ideal setting for unwinding after a day’s sightseeing. The fully-equipped, modern kitchen leads out to a sunny deck and BBQ overlooking your own tranquil, enclosed garden.

For an additional fee, you can purchase a convenient BBQ pack from Cockatoo Overboard, one of Cockatoo Island’s two cafes. Also available if needed are cots, high chairs, and extra cleaning services during your stay. In addition to heritage accommodation, Cockatoo Island also features a waterfront campground, popular amongst those wanting to sleep under the stars.