Astypalaia sailing holidays

The arid karstic island of Astypalea - Αστυπάλαια - Astypalaia - Astipalaia, the most westerly of the Dodecanese, shows clear affinities in both landscape and culture with the Cyclades.

Two wide bays on the north-west and south-east sides divide the island into a higher western half and a lower eastern half, joined by the Ayios Andreas Isthmus, which is only 110 m wide, even narrower than the Patmos' isthmus!

Stock farming (cheese), fruit- and vegetable-growing and fishing bring the inhabitants a modest degree of well-being.

View across Skala bay on Astypalaia, with the Venetian castle and Chora looking down on the “new” quay.
The architecture and ambiance is distictly cycladic: typical street in Skala and Chora.

Astypalaia is one of the least accessible islands due to location and winds, but also one of the most attractive and rewarding islands in the whole of the Mediterranean: cerulean and turquoise bays, a stunning chora, totally off the beaten track, reclusive and sheltered anchorages.

This fascinating island is well worth a three night stay and is best visited in a two-week, ideally three-week itinerary from the Athens, Kos or Paros yacht charter bases .

The picturesque village of Astypalea is dominated by a Venetian castle (13 – 16th c.) founded in 1413 by Giovanni Querini, a Venetian official of the Duchy of Naxos, as well as two important churches that were built on ancient ruins. The blue-domed panagía portaítissa is perhaps the most alluring orthodox sanctuary of the Dodecanese. The views from this elevation are spectacular and aptly called “god's bank”.

The capital is situated on a bare rocky hill above its little port (Livadi or Skala bay). South-west is the fertile Livadi valley, the island's main agricultural area.

In typical Skala (vulnerable but necessary port) and Chora (safe uphill) fashion, just 190 years ago the village of Astypalaia was paltry. Pirate raids prevented the residents from expanding the village outside its walls. It was only after 1829 that houses started being built on both sides of the road connecting the old port to the stronghold.

Scattered over the island are some 200 little churches and chapels, most of them founded by private citizens and many of them in a state of despair.

Some of the many neighbouring rocky islets are used for the grazing of goats.

Anchorages and ports

In prevailing southerlies, or when approaching from Amorgos, Paros or Naxos from the north, the little port of St Andreas - Áyios Andréas north of the isthmus is an alternative.

Astypalaia and the surrounding islands are dotted with beaches and anchorages providing suitable shelter for various wind directions.

These bays also feature the most vivid turquoise and azure colours in the Aegean Sea.
Most notably the Phokas bay - Órmos Fokás anchorages.

The striking row of eight xetrocharis type windmills, situated on the pass of the capital, have been partly restored with rotating wheeled roofs.