A perfect example of craftsmanship in Anafi is Chora, the only settlement on the island. Built amphitheatrically on a hillside right below the Venetian castle, it mesmerizes the visitor with its air of romance. Walk through the cobblestone serpentine alleys and along the white-painted domed roof houses with whitewashed courtyards and colorful bougainvilleas. Admire the picturesque windmills and beautiful chapels with Byzantine and post-Byzantine icons. The heart of Anafi beats here since the medieval years and locals as well as visitors meet in the summers for spontaneous feasts looking out to the Cretan Sea. The Archaeological Collection of Roman statues and sculptures excavated in Kastelli (ancient Anafi) is also exhibited here.
The archaeological site at the top of the hill "Kastelli", at a height of 327 meters, testifies to the glorious past of the ancient city-state of Anafi. Admire the ruins of the strong wall, outstanding remains of the necropolis with impressive tombs and Roman tombstones, such as the marble sarcophagus next to the picturesque chapel of Panagia Dokari. Nothing prepares the visitor for the view of the magnificent Kalamos, the jewel of Anafi and the most famous natural monument on the island. It is a huge limestone rock that rises 460 meters above the sea. This is the second largest monolith in the Mediterranean, after Gibraltar. Legend has it that anyone who approaches the rock feels drawn by a tremendous force.
On the highest peak of Kalamos stands the Monastery of Panagia Kalamiotissa, a small masterpiece of the 18th century, built on what used to be the site of a medieval fortress. A single-nave church with white dome and bell tower, a few cells and a cistern make up the most important religious monument of the island. The view of the endless blue of the Aegean from the monastery’s balcony is breathtaking.
Walking down from the rock, on the narrow isthmus that connects the peninsula of Kalamos with the main part of the island, is the historic Monastery of Zoodochos Pigi, one of the most important pilgrimages of the Cyclades dating back to the time of the Turkish occupation. It is built in a magnificent location, on the ruins of the ancient temple of Apollo Aiglitis, and, according to mythology, it was built by the Argonauts. The church was connected to Kasteli through the cobbled Iera Odos. Ancient building materials were used for the construction of the monastery, such as parts of the temple walls and columns.
Next stop, Drakontospilo, on the north side of Kalamos. It is one of the most unusual geological formations in Anafi, with an impressive 10-meter high opening. Its interior decoration in gold-green colors consists of columns, natural troughs, and stalactites. Access is only via a rough path.