Cockatoo Island

An island in the middle of Sydney Harbour that’s a UNESCO World Heritage site dotted with historical buildings. Catch the ferry from Circular Quay—a journey in itself—to see architecture from five distinct eras. Squat, convict-built lock-ups of Sydney’s beginnings contrast with grand-scale ship-building facilities of a once-thriving industry. Dedicate a good half-day here: there’s also a cafe, a bar, walking tracks, and several ways to interact with the history, including an audio tour and video installations. This isn’t a pretty, Disneyfied experience—it’s quite gritty. And an interesting contrast against the sparkling harbour.