The island is situated between the islands of Amorgos and Kos. It’s part of the Dodecanese group. It’s the link of the Noth Aegean islands. The first settlements were created during the Cycladic period, findings of which still exist today in the area of Mesa Vathi (Pyrgos). Vaulted tombs dating back to the Mycenean period also have been found in the areas of Armenochori – Sygero. Dwellers from Megara and Argolida (Doric tribes) also settled in Astypalea and in 496 B.C. the island was fortunate enough have it’s own Olympic champion. During the Peloponnesian war Astypalea sided with the Athenian alliance. The baths of Maltezana in Analipsi are evidence of the island’s Roman occupation. During this time, Astypalea was given autonomy and privileges like not having to pay taxes. Later on, it became part of the Byzantine Empire evidence of which still remain today through the primal Christian churches and Byzantine castle of St.John located on the western part of the island. During the beginning of the 15th century the castle overlooking Chora is built by the Venetian family Querini (a family that still exists and is very culturally active in Venice) after the island was offered to them by the Duke of Naxos. The Turks dominated the island until 1912, year when the whole Dodecanese complex is turned over to the Italians. The island returned to Greece on March 7th, 1948.
Astypalea has 5 villages: Chora and Livadi located in the southwestern part of the island, Analipsi in the center and Exo Vathi and Mesa Vathi in the northeastern part.
Chora is the capital of the island and therefore has the town hall, police station, port authority, central bank, post office, schools etc. It is a traditional settlement which covers the port of Pera Gialos all the way to the top of the hill where the Venetian castle stands. The streets that lead to the castle are lined with adjacent small two-story white houses each with their own wooden or stone stairways and tiny verandas. Along the way one can see small churches and of course the island’s trademark Windmills. Restaurants, fish taverns, cafes, sweet shops etc, are spread all throughout the town and cover a wide variety of tastes. At night, a lit up Chora and castle complete the magical scenery.
Livadi is located about 1.5 km to the southwest of Chora and has become one of the most popular places to stay and visit during the day. It is one of the few places on the island that’s covered in green. Vineyards, tangerine orchards and gardens give away the presence of the local dam which provides the whole island with precious water, while on the southern most part of the settlement one can find the island’s most beautiful and organized beaches. Lined with taverns and cafes this area is one of the most popular places during the summer months.
Analipsi is located about 9.5 km to the northwest of Chora and is a traditional fishing village. Although it has started to develop in the past few years, it is still a quiet village, ideal for those who want a more laid back type of vacation. One can take a small stroll on the pier and buy fresh fish from the local fishing boats, or can dine at the small taverns and cafes.
Ten and 12 km further north from Analipsi are situated the small rural villages of Exo and Mesa Vathi. Even though these villages were large enough in the past to have their own elementary school, today only one or two families reside in Exo Vathi, while four or five in Mesa Vathi. Mesa Vathi has the area’s only fish tavern.