Pyrgos

Though today Pyrgos has only 500 inhabitants, until the early 1800s it was the capital of the island. Medieval houses are stacked on top of one another and back-to-back for protection against pirates. Your reward for a climb up the picturesque streets ends at the ruined Venetian castle, where views extend across the vineyard-studded landscape to both coasts. In Pyrgos you are really in old Santorini—hardly anything has changed.