Ano Syros (Chora)

Ano Syros, the old Chora of Syros, crowns a conical hill above Ermoupoli, its whitewashed houses spiralling up toward the cathedral at the summit. It is one of the most distinctive medieval settlements in the Cyclades, built in the Middle Ages by Venetians and Latin settlers, and it stands in strong contrast to the neoclassical port city below. Whereas Ermoupoli was founded in the 1820s, Ano Syros goes back centuries earlier, and Byzantine rule gave way to a Venetian one after 1204. The Venetian period shaped its plan, and it has kept its Catholic character, with Catholics a significant part of the island's community and Catholic churches alongside Orthodox ones.

The settlement is a maze of stepped lanes, arches and vaulted passages. Houses are packed tightly together, with continuous walls that formed a kind of defence against pirates, and few lanes are wide enough for more than a pedestrian. Cars are left at the foot, and the approach is on foot or by narrow roads around the hill. There are several ways up, most of them by long stairways, and a walk from Ermoupoli takes about half an hour. As you climb, the neoclassical mansions of the port fall away below, and the view over rooftops and sea opens out.

At the top stands the Catholic Cathedral of Saint George, a white church with a long history, and nearby are the Capuchin and Jesuit convents, reminders of the long Western presence on the island. Chapels, small squares and doors painted in bright colours fill the lanes. Ano Syros is also the birthplace of Markos Vamvakaris, a founding figure of rebetiko, the urban music of Greece, and the music is still part of local life, with tavernas and small venues playing it in the evenings.

From the summit, the Aegean Sea is spread around you, with Tinos, Mykonos and other islands visible on a clear day. Below, Ermoupoli, the capital of the Cyclades, shows the domes and towers of its Orthodox churches, the Apollo Theater and Miaouli Square. It is worth exploring both: the contrast between the two towns tells the story of Syros.

Syros can be reached by ferry from Piraeus, which takes a few hours depending on the vessel, or from other Cycladic islands, and there are flights from Athens. Wear grippy shoes, since the stairs are steep and polished, and carry water. Sunset from the upper lanes is excellent, and late afternoon avoids the midday heat. Shops and cafes keep irregular hours outside summer, so plan flexibly.