Kastro

Perched on a rocky headland on the eastern coast of Sifnos, Kastro was the island's capital for more than two thousand years, from antiquity until 1836, when the seat of government moved to Apollonia. The ancient settlement here is the "city" described by the historian Herodotus, which flourished in the 6th century BC with a theatre and a temple dedicated to Dionysus. Later, after the Fourth Crusade, the island passed into the Venetian-ruled Duchy of Naxos in 1207, was briefly recaptured by the Byzantines in 1269, and by 1307 had fallen under an independent Hospitaller lord — each period leaving its mark on the settlement's defenses.

What makes Kastro unusual is that its houses double as the fortification wall itself, a classic Cycladic kastro layout in which the outer row of dwellings forms a continuous defensive ring around the hill. Losing its status as capital in 1836 effectively froze the village in time, sparing it from the later development seen elsewhere on Sifnos and leaving a dense maze of stone lanes, chapels and old mansions largely intact.

Kastro has no proper harbor of its own and offers little shelter for visiting boats, so most charter guests view it from the water or arrive by road from the nearby port. Even so, its dramatic setting and layered history make it a popular stop for gulet charter guests exploring Greece.