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 islands 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 islands history. The portrait of Chora with its white body and ocean blue heart, leaves the visitor speechless because of, its beauty and harmony.
The Castle takes up all the plateau at the top of the hill and used to be densely built group of houses which made up the Middle Ages settlement. Today, only a few of the houses have survived, the outside walls of which make up the walls of the Castle.
The panoramic views of Chora and Livadi at the outset and the view of the tranquil mountains with the scattered, white monasteries offers a unique pleasure to the viewer. On this same route is the monastery of Flevariotissa.
Since the monastery of Flevariotissa's festival is celebrated on the 2nd February, it is the winter rendezvous of Astypalaias friends from all over the world. This route comes to an end in the area called Agios Ioannis (Saint John) which is 16 kilometers away. The picturesque, whitewashed church is set between two abrupt hill slopes near the open sea.
Two of the most beautiful beaches of the island can be reached by the tourist boats which set off from Pera Yalos and Maltezana. These beaches are Kaminakia, where there is a tavern which serves boiled goat (stew), an island speciality, and Vatses, where there is a cave with stalactites and stalagmites.
