The westernmost island of the Dodecanese but truly and deeply Cycladic, Astypalea is one of the most beautiful islands in the Aegean, with beautiful beaches, a remarkably picturesque Hora and most importantly, friendly people.
The island is shaped like a butterfly, where the western island is more beautiful and with better beaches and places to visit. The terrain is mostly dry, mountainous, with rough roads leading to nice beaches with crystal clear and cool waters.
Astypalea has a long history, ranging from the Protocycladic times, to the Golden Age and the Athenian Alliance, to the Roman times, the Byzantine times and lately to the Venetian rule, the Turks and the Italians, where in 1948 it was reunited with the rest of Greece. The impressive and beautiful Hora of Astypalaia has architectonic elements that have been formed in its various historic phases according to the social and economic conditions that prevailed in each. Its Castle and the medieval fortified settlement is a significant monument, one of the most remarkable in the whole Aegean.

The more recent phases are still dependent on the initial settling core of the castle, in the interior of which residents would always take refuge in cases of emergency. All roads on the external ring lead to the castle’s gate, following the hill’s topography. the capital and port of the island built on a hill protruding into the sea thus forming two bays: the port - Pera Yialos -and Livadi Bay. The peak is dominated by the fortress built of dark local stone from which one can see the glowing white domes of the Evangelistria and Aghios Georgios Churches sticking out. Around it are white houses with blue doors and windows and wooden railings on the balconies.
Among them are churches and domed chapels. On the saddle of the hill are eight windmills, a unique jewel adorning Hora. Slightly further on is the traditional coffee house and further still is the Town Hall from whence the two main roads which lead up the hill to the Fortress begin. Each leads to a well known church, the Monastery of Panaghia Portaitissa on the Livadi Bay side and the Megali Panaghia Church on the Pera Yialos side.
Livadi, A seaside village spread along a fertile valley on the inlet of the bay with the same name. Livadi is the island's flower garden. The gardens with mandarin trees, orange trees, vines, and houses bedecked in flowers are spread along the entire length of the stream which terminates at a beautiful beach.
Vathi resembles are lagoon. The bay is almost completely closed off with an opening of just 50m. There are two small villages at Vathi: Exo Vathi which is at the mouth of the bay with its small jetty at which caiques moor and Mesa Vathi on the inlet of the bay with fields, a few trees and vineyards. Visitors can reach Vathi by road along a passable dirt track or by boat. There are regular sailings from Vai Bay.

Analipsi or Maltezana
A seaside village spread out along a small valley in Exo Nisi with a beautiful sandy beach. The second name 'Maltezana' makes reference to the pirates who pillaged the Aegean and found refuge in the island's sheltered bays. The village hugs the bay with a long jetty at which fishing caiques moor. The orchards and vineyards go right down to the water's edge. Tour boats can take visitors to the island's beaches and the islets of Hondro, Ligno, Aghia Kyriaki, Koutsomytis, Syrna and Kounoupi.

Other islets in the area

To the southeast are the islets of Hondro, Ligno, Aghia Kyriaki with a church dedicated to that saint, Koutsomytis with its charming beach and Kounoupi. Further out are Adelfi, Syrna and the Tria Nisia. To the west are the islets of Ktenia, Pontikoussa, Ofidoussa and Katsagreli. To the north is Fokionisia.
It is the island’s most important sight. Placed on Hora’s loftiest point, on the remains of the island’s ancient acropolis and of the byzantine castle, it was initially constructed by Giovanni I Querini in 1207 and completed by Giovanni IV Zanachi Querini in 1413.
The castle offered protection, which resulted in an increase of its population, reaching 4,000 inhabitants. The densely built castle with the narrow, cobblestone alleys also included two towers, one on the gate where the feud owners resided and one with four storeys on the south side, the so-called “Sarai”. The abandonment of the castle began in 1830, when piracy was no longer a threat and by 1948 it was completely deserted.

Kylindra archeological site
It is located in Hora in hill Katsalo.
This is an ancient cemetery of infants, probably one of the largest ever to have been discovered. According to the 22nd Ephorate of Prehistoric and Classical Antiquities, this ancient cemetery was used from the Late Archaic up to the Roman times (600 b.C.-200 a.C.). The dead infants were placed inside clay vessels and buried. Some 2,000 burials have been discovered to this day and one such vessel is on display in the Archeological Museum of Astypalaia.
Tallara Post-Roman Baths
It is in Maltezana or Analipsi.

The Old Christian baths of Tallara, also known as the Baths of Maltezana, incorporates some of the excavations’ most impressive findings. More specifically, visitors can see mosaics depicting the four seasons, the zodiac and Time holding earth in his hand.
Astypalea has been settled from prehistoric years. Its first inhabitants were probably Kares, who called it Pyrra. It was then conquered by Minoans from Crete and later by Achaeans from Megara. Settlers from Epidavros must also have set foot on the island, influencing the local dialect. Today’s name Astypalea ("palaion asty" = "old city") seems to derive from the period when it was used as a commercial station by Phoenicians or, according to mythology, from the daughter of Phoenix and Perimede.
In 105 b.C., Astypalea allied with the Romans, who considered it of crucial importance in the struggle against pirates due to its central location. During Frankish rule, it was part of the Naxos duchy under Markos Sanoudos. After the fall of Constantinople, Astypalea was conquered by Venetians in 1207, and more specifically by the families of Querini and Grimani, who built the Castle at the top of Hora, in the position where a Byzantine castle and before that the ancient acropolis used to be.

In October 2, 1540 it was conquered by the Turks. In 1830 in the London convention that determined the borders of the infant Greek state, it was decided for the island to remain under Turkish rule. In 1912 it was taken over by the Italians. Italian rule lasted until 1943 and in 1948 Astypalea was annexed to Greece along with the rest of the Dodecanese.