Bygone eras have left a tangible mark on ancient Astypalaia - the Venetian Castle (dating back to the 13th century) perched on top of the hill in Chora monumentalizes the Guerini family's Venetian rule that lasted (nearly uninterrupted) from 1204 all the way through to 1537. This long Venetian period was followed by a comparable stretch of Turkish presence on the Dodecanese islands - Turks left in the early 20th century, only to give way to a sequence of conquerors - the British, Italians, and Germans all enjoyed a brief presence in Astypalaia before the island was eventually back under Greek jurisdiction in 1948.
Astypalaia today is a treasure ground of ancient architectural remains, scenic spots, and secluded beaches. The island's remote charm comes at a price of little to no infrastructure, especially in the outlying areas, but the trade-off is certainly worth its unparalleled tranquility and pristine quality. Thanks to the island's longstanding fishing tradition and incredible marine wealth, fish and seafood are abundant in local taverns (along with home-grown, organic produce), which are aplenty in the settlements of Chora, nearby the port of Pera Gialos, travelers' darling Maltezana (Analipsi), and the tiny villages of Livadia and Vathi.
The island's main port and capital, Chora is the hot-spot for shopping, dining, and cultural pursuits. With its scenic cascade of white houses running down from the Venetian castle atop the hill, windmills, museums, and a plethora of photo-ready locations, it is certainly not to be missed.
Nine scenic whitewashed windmills under maroon wood roofs stand at an elevation on the hillside of the island's Chora. The well-preserved, picture-perfect windmills possibly date back to as early as the 18th century, and are one of the island's main visitor attractions.
Archipelago Cafe & Bar
The outdoor terrace framed with lush green trees and fragrant flowers invites for coffee and cake with a view over the stunning hill of Chora. Archipelago Cafe & Bar serves a vast array of sweets and cakes, as well as drinks after sundown when the town beautifully lights up.
Good to know
Public buses run relatively frequently during the summer, connecting the Chora (buses stop in Chora Square) to other larger destinations throughout the island, such as Pera Gialos, Maltezana, and Livadi. During low season, however, buses are infrequent, and travelers would be better off renting a car or hiring a cab.