The island's capital wraps around one of the deepest natural harbours in the Aegean — Vathy literally means "deep" — with neoclassical houses climbing the hill behind. The waterfront is genuinely working: ferries to Piraeus, fishing boats, customs and harbour offices, and a strip of cafes that's the social heart of the island.
The old town of Ano Vathy, perched on the slope above, is the more atmospheric side: narrow streets, blue shutters, a couple of old churches, and a hillside of wood-and-plaster houses that came over from Asia Minor with the 1922 refugees. Walk up at dusk, then come back down for dinner by the water.