Though today Pyrgos has only 500 inhabitants, until the early 1800s it was the capital of the island. Stop here to see its medieval houses, stacked on top of one another and back to back for protection against pirates. The beautiful neoclassic building on the way up is a luxury hotel. The view from the ruined Venetian castle is panoramic. And reward yourself for the climb up the picturesque streets, which follow the shape of the hill, with a stop at the panoramic terrace of the Café Kastelli, for Greek coffee and homemade sweets. In Pyrgos you are really in old Santorini—hardly anything has changed.