A bridge between the two major island complexes of the Aegean Sea, the Dodecanese (to which it belongs) and the Cyclades, Astypalea has many Cycladic elements: the anhydrated landscape with the shrubs, the acropolis with the whitewashed houses around and the picturesque chapels in every corner .
According to mythological tradition, the island owes its name to Nymph Astypalaia, daughter of Phoenix and Poseidon’s wife. Astypalea was inhabited since Prehistoric times. Its first inhabitants are the Kares and later the Minoans. During Hellenic Times, Astypalea developed great naval activity and became known thanks to its rich fish (“fish”) and its abundant agricultural products. During the Byzantine Times or Astypalaia belonged to the Province of the Islands, and after 1204 fell into the hands of the Venetians, who preserved their sovereignty (except for a short period) until 1537.
The capital of the island, Chora, is built on a hill that enters the sea, forming two mountains: the port (Pera Gialos) and the Livadia meadow. At the top dominates the castle with the dark local stone, where the Virgin of the Castle (Evangelistria) and Agios Georgios emerge. The inhabitants are the houses that tighten the castle giving Cycladic color to the settlement, while at the edge of the hill stand the well-preserved windmills, the golden Chora.
The castle of Chora, the Venetian castle of Kourini, belongs to the architectural aspect of the fortified settlement type, with the external houses creating a wall with small windows for jams.
The religious monuments that stand out are the church of Panagia Portaitissa (middle of the 18th century), with a wooded iconostasis and a beautiful bell tower, one of the most beautiful in the Dodecanese, and the Great Virgin Mary, with a mountain floor in the courtyard.
Significant are the exhibits of the Archaeological Museum of Astypalea, dating back to the Prehistoric to the Medieval years (among others, findings from Mycenaean tombs, the treasure of silver coins of Classical Times, sections of early Christian basilicas, marble coat of arms of the Kournini family from the castle of Chora).
Outside of Chora are the monastery of Panagia Flevariotissa (6 km northwest), built on a sloping slope, and the monastery of Agios Ioannis (12 km D), built in imposing area overlooking the sea (across from the monastery lies the came under the local tradition of Ai-Giannis Castle).