The capital of Astypalaia (pronounced as ‘asti–pa–le-a’) is Chora characterized by its unique architecture. Located in the western part of the island, it is built amphitheatrically on the hill, and considered as one of the most beautiful settlements of the Aegean Sea. The port at the foot of Chora is called Pera Gialos. Previously it was a separate village, but today it has joined with the town. At the top of the village stands the Venetian Castle, built in dark, local stone, surrounded by the whitewashed cubic houses with blue windows and doors. On the neck of the hill is the central square of the island where one will also find the eight traditional stone windmills. Most of them have been repaired or maintained recently. They are cylindrical in shape and belong to the class “xetrochari” mill, whose roof is turned depending on the direction of the wind. They are in excellent condition are most of them, still in use. In fact, one hosts the municipality office, where information leaflets about the island can be found. Another is used for various exhibitions and events organized during the summer. They previously served the needs of residents, but now are characterized as historic monuments.
Following the road from the windmills (near the central square) of the Chora and descending westward you are lead to the seaside village of Livadi. Spread along a fertile valley on the inlet of the homonymous bay Livadi is a small seaside settlement where one sees green and is the most productive and fertile in the island. In this valley, orchards tangerine, pomegranate, lemon trees, orange trees and vineyards can be found. It also has the most organised beach of the island with crystal clear waters for swimming and water sports from where you can gaze at the vastness of the sea but above all the wonderful image of the Venetian Castle. In Livadi, there are several taverns, ouzo bars, supermarkets located literally on the coastline and facing the country and the castle.
In the north-west corner, in the “back” of the valley, the dam of the island can be found. This is where the water streams are collected during the rainy season. It forms an artificial lake which covers the water needs of the island.
A superb option to stay, the Livadi has many rooms and the beach is approximately 1.5 km from the city. Furthermore, it is considered the starting point for excursions to the other beautiful beaches of the island. Following the uphill end of the beach after a 5×5 football court, the traveler meets the settlement of St. Basil.
In the eastern part of the island is the second largest settlement, the Maltezana or Analipsi. It is a seaside village with a nice sandy beach, situated within a valley. The name probably came from the Maltese pirates stationed in the area. A feature of the town is the harbour with the fishing boats and nets spread out. From there the entire island is supplied with fresh fish. In recent years Maltezana has shown intense tourist development.
The Vathi is a secluded cove that is the safest bay on the island. Its disadvantage is that is shallow (only 2.8 meters at certain points) which makes it look more like a lagoon. There are two settlements, the Outside Vathi, situated at the entrance of the bay with a small staircase where boats tie up, and the Inside Vathi, in the gulf, with farmland, trees and vines. The distance between the Outside and Inside Vathi is about 2 km).
One of the characteristic features of Astypalaia are the many islets surrounding it, which administratively belong to it. The islets are Chondro, Ligno, Aghia Kyriaki with the chapel, Koutsomitis with the beautiful beach, Kounoupes at the southeastern side of the island, the Ktenia, Pontikousa, Ofidousa and Katsagreli west, while to the north are the Fokonisia. The islet of Aghios Fokas was separated by the water level from the island in 1956. A dry strip was cut to form a new island baptized with the name of the small church she “took with her.” A little further are the Aderfia and Syrna.