Ano Syros is the older of Ermoupoli's two hills, a medieval Catholic settlement that predates the neoclassical town below by several centuries. The streets here are narrow enough that you can touch both walls simultaneously, the houses stacked on top of each other as they climb toward the Cathedral of San Giorgio at the summit. It is exactly the kind of place you want to get lost in — and exactly small enough that getting lost doesn't matter.
The views from the top are exceptional: the rooftops of Ermoupoli cascading down to the harbour, the Orthodox hill of Vrodado facing you across the valley, and on clear days the other Cycladic islands visible on the horizon. The Catholic church community has maintained its distinct character for 800 years, and the neighbourhood still has a quieter, more village-like atmosphere than the bustling port below.