Astypalaia is an island in the Dodecanese. It is shaped like a butterfly, with the two wings (the western Mesa Nisi and the eastern Exo Nisi) joined by a narrow strip of land. The island has high crags, fertile valleys, and dozens of small bays.
Chora, the capital, is on a hillside overlooking the port of Petra Gialos. It is the oldest settlement on the island and one of the loveliest in the world.
Chora is dominated by the Venetian castle on the hilltop, built by the ruling Querini family in the 13th century. There are also two impressive churches up there, Panagia Evangelistria (1853) and Agios Georgios (1790), the best spot to watch the sun set.
At Chora's entrance are 8 impressive preserved windmills, 2 of which are open to the public.
On the road from the town hall to the castle is one of the most gorgeous churches in the Dodecanese, Panagia Portaitissa. Built in the 18th century, the church has a carved, gilded wooden iconostasis, and is next to the Ecclesiastical Museum, which houses a collection of rare coins.
The Archaeological Museum at Pera Gialos showcases finds dating from prehistoric times, along with the marble crest of the Querini family.
2 km south of Chora, in a fertile valley with mandarin trees, vineyards, and vegetable gardens, the village of Livadi is popular with visitors, as is Maltezana in the northeast.
The delightful, time-forgotten fishing village of Vathy, 21 km from Chora, is located in a protected bay that resembles a lagoon. Driving there along a dirt road, you'll see farmhouses, small monasteries, beehives, and wild goats on the fragrant, herb-covered slopes. Visit Drakos Cave with its impressive stalagmites and stalactites. The Church of Panagia Poulariani is built on a rock shaped like the Virgin Mary holding the baby Jesus, and is reachable only by boat or on foot. In a wonderful mountain landscape lies the Panagia Flevariotissa monastery compound, part of which is inside a cave.
Astypalaia makes a nice stop in a sailing trip. It has anchorages and a marina with some restaurants ashore.
- Vatses, the best beach, accessible via dirt road or by boat. At the end of it is a bar with relaxing music and excellent cocktails.
- Pera Gialos, popular sandy beach with deep, cool waters.
- Livadi has plenty of amenities.
- Agios Konstantinos, sandy with plenty of amenities, connected by footpath to its nearby twin Tzanakia.
- Plakes, toward Maltezana, this rocky beach has light blue waters and is ideal for diving. Further down the road is beautiful and sheltered Ble Limanaki, but get there and leave early to avoid the crowds in August when the wind picks up.
- Kaminakia, stunning and sandy, with deep emerald waters.
- Boats provide services to the islets of Kounoupes and Koutsomitis which have magnificent beaches and are surrounded by turquoise waters.