Until the 19th century, Chora was the only settlement of the contemporary years of Astypalaia. The other settlements which exist today were created in the uncultivated spots of the island.

The biggest of these settlements are Livadi and Analypsi or Maltezana, created during the Italian years. Most of the island's life is concentrated in Chora. It is built on a peninsula which is bathed by the serene sea creating two tranquil bays called Pera Yalos which is situated on the left as we look at the open sea and Livadi which is on the right. The Venetian Castle, with its two whitewashed churches, stands proudly at the top of the peninsula proclaiming the onset of the development of the settlement.

As the centuries progressed, little white houses began to appear outside the walls of the castle which covered the hill and reached the port of Pera Yalos joining together to form a mosaic of our island's history. The portrait of Chora with its white body and ocean blue heart, leaves the visitor speechless because of, its beauty and harmony.

According to Greek mythology, Astypalaia and Europe were the daughters of Finikos and Perimidis. From the union of Astypalaia and Poseidon, god of the water, the Argonaut, Agaeos was born and so was first settled by the Kares who named her "Pyra" for the red colour of her soil. Because of her many fragrant flowers and her fruit, the Ancient Greek called her "the God's Bank".

Astypalaia has gone through the Occupation of Crete, the Minoan Era and later on became Greek because of settlers who came from Megara.

During the ancient years, the island must have shown a significant climax as can be witnessed by the various findings, mainly coins which were found during excavations and from the frequent references in texts of ancient writers. The findings are on display at the Archaeological Museum which is open to the public at Pera Yalos and where the visitor can begin to understand the life of Astypalaia.

During the Hellenistic Era, it was a port (a station of Ptolemy of Egypt) and during the Roman Period, it showed a great development owed to its abundant, natural ports which resulted in starting points against the pirates. During the Byzantine Ages, the escalation of piratism brought about changes to the architectural structure and location of the houses of the island, such as the decline of the coastal dwellings and the movement of the population within the constructed walls of the castle for protection. This era marks the construction of the Castle of Agios Ioannis, situated on the southwestern coast of Astypalaia, whose remains can be found up to today.