Sydney is the city that Australia puts on its postcards, and for once the postcard isn't lying. A sandstone peninsula between two coves, the sails of the Opera House on one side and the steel arch of the Harbour Bridge on the other, ferries crossing in between as if it were a street. The harbour is the reason the city is here. The Gadigal people of the Eora nation lived on its shores long before 1788, when Captain Arthur Phillip's First Fleet of convicts and marines dropped anchor in Sydney Cove and founded the first European settlement in Australia.
What makes it a great city to spend five days in is that you don't have to choose between a city break and a beach holiday. Sydney does both, by public transport, on a single card. In the morning you can be on a guided tour inside the Opera House, by lunchtime on a ferry to Manly, and a day later walking the cliffs from Bondi to Coogee, then two hours west of the center on a train that ends at the edge of a sandstone canyon. Five days lets you do all of that without running. Three would force you to drop the beaches or the mountains.
This plan is organized by water and geography. Day one is the Opera House and the Royal Botanic Garden, day two the Harbour Bridge and The Rocks, day three the harbour by ferry (Taronga Zoo and Manly), day four the ocean beaches and dinner in Surry Hills, and day five a day trip to the Blue Mountains. Start on a Thursday: The Rocks Markets run only Friday to Sunday, Susannah Place is open only Thursday to Saturday, the weekend suits the ferry and beach days, and the Blue Mountains day lands on a Monday, when the lookouts are quieter than at the weekend. You'll also find tips for visiting in November (late spring) and December (summer), including how to see the New Year's Eve fireworks. For the bigger picture, see our page on Australia.