Astypalaia

Astypalaia, the ‘Butterfly of the Aegean’, sits at the boundary between the Cyclades and the Dodecanese, and its architecture reflects both traditions — whitewashed Cycladic cubes stacked beneath a Dodecanesian fortress. The island is shaped like a butterfly, its two hilly halves connected by a narrow 100-metre-wide isthmus called Steno. The hilltop capital Chora is crowned by the Querini Castle, a 13th-century Venetian fortress offering sweeping views across both wings of the island. Restored windmills at the town entrance have been converted into a library and information centre. Below Chora, the old port of Pera Gialos serves fresh seafood in harbourside tavernas. Astypalaia is also Greece’s first ‘smart green island’, with a Volkswagen-backed electric vehicle sharing fleet and electric shuttle buses reducing fossil fuel use. Boat trips reach the uninhabited islets of Kounoupes and Koutsomiti, whose translucent waters and castaway beaches feel entirely untouched. The island’s wild interior is crossed by old Venetian hiking paths connecting remote beaches like Vatses and Agios Konstantinos.