Cockatoo Island

Once a prison, later a reform school, then one of Australia’s busiest shipyards, Cockatoo Island now sits right in the middle of Sydney Harbour looking faintly unconcerned by its own history. Ferries glide past the Opera House and expensive waterfront apartments before dropping visitors into a world of rusted cranes, sandstone tunnels and industrial sheds large enough to make nearby office towers feel slightly insecure.

Convicts began reshaping the island in the 1830s, carving sandstone by hand to build what became Australia’s first dry dock. Standing beside it today, the scale still feels surprising. People tend to stop talking for a second when they first look down into it. During the Second World War, more than 4000 workers packed the island building and repairing naval ships around the clock. It must have been deafening. Today the loudest residents are the cockatoos, which still sound permanently dissatisfied with management.

The appeal of Cockatoo Island comes from its atmosphere rather than beauty in the traditional sense. The old turbine halls still carry traces of oil and salt air. Steel staircases creak. Enormous gantry cranes frame views of the Sydney skyline in ways no architect would dare propose in a luxury apartment brochure. Then suddenly there is grass, harbour light and people drinking wine beside century old warehouses as if this were the most natural thing in the world.

The island is UNESCO listed for its convict history, though what stays with many visitors is the strange contrast between raw industrial heritage and one of the world’s prettiest harbours. You can even spend the night here, which means few Sydney experiences are quite as memorable as waking up inside a former shipyard with ferries crossing the water outside your tent. Convicts had a somewhat different hospitality experience, admittedly.