It has been inhabited since the Prehistoric Age. The Romans had had Astypalaia as a base against the pirates. Later it has been conquered by the Venetians and the Turks. In 1821 it took part in the revolution against the Turks. In 1912 was conquered by the Italians. On 17 March 1948 was officially integrated with Greece.
Astypalaia is in the far west region of Dodecanese, a bridge between them and the islands of Cyclades. It is extended in an area of 97 sq.km. and in a distance of 175 n.m. (approx.10 hours ) from Piraeus.
The name Astypalaia means old city and is alike two islands joioned by a narrow strip of land 100 metres approximately wide, "the Narrow Passage" (Steno) as the inhabitants of the island used to call it, separating it in the eastern "Messa Nissi" (inner island) and the western "Exo Nissi" (outside island).
The capital Astypalaia or Hora is magnioficent, impressive with bright tense colours in the houses and distinguished architectural style, built in a hill penetrating the sea forming the bays Pera Ghialos to the left side and Livadia to the right. The Venetian castle of Guerini is situated glorious at the top of the peninsula signalling the starting point of the development of this settlement. Internally there are the small churches of St.George and Evanghelismos (Annunciation). In an extent around the castle there are located the houses and in the background we can distinguish eight well preserved windmills.
Under the castle it is situated the enchanting church of Panaghia Portaitissa of the 18th century. Nearby it is housed a small ecclessiastical collection of old icons.
In the Archaeological Museum in Pera Ghialos you have the opportunity to see findings from tombs of Mycenaean age, marble coat of arms of the family Guerini and findings of the Classical, Hellenistic and Roman Age.
The monastery of Panaghia Flevariotissa is built in a hillside and a part of the church is located in a cavern.
In a region full of trees and in a distance of 12 km. from the capital city it is situated the monastery of St.Ioannis with a marvellous view to the sea and the nearby islets.
Of interest is also the water dam of the island as well as an excursion to the Panormos bay.
9 km. northwards Hora, in Exo Nissi (Outside Island) there is the beautiful by the sea village Analipsi or Maltezana built in a deep bay. It is a picturesque settlement with white houses, flowers and orchards. From here they set off the boats for the beaches and the around islands.
In the end of the village it is the small church of Analipsi (Ascension). With an excursion boat you can visit the church of Panaghia Poulariani.
The settlement by the sea Livadia, 3 km. from Hora is built in a green landscape. Worthwhile sites are the cavern of Negros where you can go by boat from Hora, as well as the bays Vatses and Kaminakia with the fantastic beaches.
Vathy is at a distance of about 20 km. from Hora and is situated in a very closed bay that looks alike a lagoon. It consists of the settlement Exo Vathy (Outer Vathy) in the entry of the bay and Messa Vathy (Inner Vathy). From Exo Vathy you can visit the Cavern of Dragon (Spilaio Drakou) by boat. There are impressive stalactites and stalagmites.
With excursion boats you can also visit the islets Hondro, Ligno, St.Kyriaki, Kounoupi, Fokies.