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.

Ancient monuments and sites of archaeological interest

The Tallaras Baths in Maltezana are Hellenistic baths with mosaics unique in Greece with blue and terracotta colours. They are in a good state of repair and the compositions are interesting with the subject being the seasons of the year and the symbols of the zodiac.

The Monument to the French admiral Bignon, leader of the struggle against the pirates at the beginning of the 18th century, located near Schinonda. There is a Heroes Monument in Hora.

Monasteries and Churches

The church of Panaghia Portaitissa in Hora, white with a charming bell tower, stands below the Fortress in Rhodia – a poetic place name taken from the tree which stood in the church’s grounds. It is one of the most beautiful churches in the Dodecanese. It was founded by Blessed Anthimos in the mid 18th century.

It has a carved wooden iconostasis covered in fine gold leaf, unique for its kind. Tradition says that the icon is an imprint of an icon from Iviron Monastery on Mount Athos. They say that the wood was placed atop the icon and it copied itself. Next to Panaghia church is a small ecclesiastical collection with old icons.

Drakou Cave
Drakou Cave is at Vathy with impressive stalactites and stalagmites. Get there from Vathy by caique or on foot (around 2 hours along dirt track). Negrou Cave is in Vatses Bay. Tradition links it with pirates and their treasures. Get there by boat from Hora. Trips to the cave and nearby islets are organized..