After a long ferry trip, you will reach Anafi, a small island (38 km²), at the southeastern end of the Cycladic archipelago. This geographic isolation makes Anafi ideal for relaxation, as it has not yet been affected by tourism, which contrasts sharply with the nearby island of Santoríni.
Anavasi made the signpost for the munisipality of Anafi.
And Anavasi wrote the website page about the six signposted "Footpaths of historical and cultural interest" - with a map and a pdf of the booklet "Walking Anafi" - see http://anafi.gr/en/ and http://anafi.gr/wp-content/uploads/2015/04/anafi_walking.pdf
Take a look at their website http://anafi.gr/en/ as it proposes some interesting hikes on Anafi: the hike to Panagía i Kalamiótissa is really quite exceptional, but also the two hikes from Roúkounas to the monastery of Zoödochos Pigí are really very nice.
In mythology, "Anaphe" appeared from the sea by order of the god Apollo, and this to offer a shelter to Iasoon and the Argonauts after a heavy storm.
Archaeological finds have demonstrated that Anafi was inhabited in antiquity. A road leads from the pictures que harbour of Agios Nikolaos up to Hora, the only settlement of any size, built on a naturally amphitheatrical site in the centre of the island.
Because of the volcanic eruption in the year 1650 BC, which created the present-day spectacular view of Santorini and its volcano, also at Anáfi thin layers of pumice stone came down at certain places. Later on, the history of Anáfi ran parallel to the history of the other Cycladic isles: in the year 1207, for instance, it was also annexed by Marco Sanudo, the king of the Latin-Venetian state of Náxos, and in the year 1537 it became Turkish.
Because the island suffered a lot from invasions by pirates, it depopulated almost completely – which still explains the absence of terraces for agriculture and of donkey trails. In 1956 Anáfi met with the same fate as Santoríni and it was almost entirely destroyed by the earthquake.
The small island is very mountainous with a relatively high summit: the Vìgla is 585m high. The interior is very dry, but still there are a couple of deep and narrow valleys, remarkable because of the dense vegetation consisting of all kinds of large cacti.
The celebrated Drakondospilo (Dragon's Cave) stands on Kalamos hill, near the monastery of Panagia Kalamiotissa on the south-eastern side of Anafi. It is of singular beauty because of its great variety of stalactites and stalagmites and is considered one of the most significant sights on the island.
The harbour of Agios Nikólaos is very small and it is connected with the main town of Chóra by means of the one and only asphalt road. Because of its amphitheatre-shaped location and also because of the wind mills on the slope of the hill, Chora is really very picturesque and attractive. Striking is that most of the houses, also the newer ones, are built with a vaulted roof – which offers better resistance against earthquakes. Also remarkable are the baking ovens, although these days they are only used sporadically. All together there are only about 300 people living in these two villages.
The island also offers a number of interesting archaeological sites:
In the Katalimatsa region on the south-eastern edge of the island excavations have brought to light the ruins of an ancient city which, in its largest part, is sunk in the sea. It is believed that the ancient port was situated there and concentrated the largest aspect of the financial life of the island.On the slope of the Kastélli (325m) a little downwards there is the chapel of Panagía tou Dókari with a very nice Roman sarcophagus in front of it.
No doubt the most impressive sites are the two monasteries on the eastern point of the island: the monastery of Panagía Zoödóchou Pigís at the foot of and the monastery of Panagía i Kalamiótissa on the side of the 450-metres high Kálamos. The large monastery of Zoödóchos Pigí is built on the rests of the temple of Apollo and it has incorporated large parts of the old temple wall in the new walls. The big festival (the Panigýri) takes here place on the 8th of September. The high monastery of Panagía i Kalamiótissa is marvellously situated on one of the summits of the Kálamos (hence its name). The panoramic view in itself (sometimes all the way to Crete, usually with all the surrounding Cycladics, whereby especially the island of Amorgós with a view on the monastery of Panagía Chozoviótissa is remarkable!) is worth the trip to Anáfi.
Anáfi also possesses a couple of beautiful beaches on the south coast, with amongst others the beach of Roúkounas (which is the longest one), the beach of Klisídi (which is closest and which can be reached on foot) and the small beaches underneath Agii Anárgyri (also to be reached on foot from the monastery of Zoödóchos Pigí).
There is a good bus connection between Chóra and the monastery and by means of this bus you can also get to the beaches of Roúkounas and to the ones underneath Agii Anárgyri.