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Possessing an elegant collection of grand townhouses that rise majestically from the bustling, café-lined waterfront, ERMOÚPOLIS – once Greece’s chief port – is one of the most striking towns in the Cyclades, and is certainly worth at least a night’s stay.

Medieval Sýros was largely a Catholic island, but the influx of refugees from Psará and Híos during the nineteenth century created two distinct communities. Today, the Orthodox community accounts for two thirds of the population; Lower Ermoúpolis is mostly Orthodox while the Catholics live in the Upper Town and in the majority of the villages. They do, however, commonly celebrate each other’s festivals (including Easter on the Orthodox dates only), lending a vibrant mix of cultures that gives the island its colour.

Platía Miaoúli and around

The long, central square, Platía Miaoúli, is named after an admiral of the War of Independence whose statue stands there, and in the evenings the population parades in front of its arcades. The bougainvillea-covered pedestrian street of Roïdi and side streets east of Miaoúli square are peppered with most of the better eating options.

Up the stepped street (Benáki) to the left of the town hall is the small archeological museum (Tues–Sun 8.30am–3pm; free), with three rooms of finds from Sýros, Páros and Amorgós. To the left of the clock tower more steps climb up to Vrondádho, the hill that hosts the Orthodox quarter. The wonderful church of the Anástasis stands atop the hill, with its domed roof and panoramic views over Tínos and Mýkonos.

Below Miaoúli square, and down a side street you can find the elaborate Casino and the Church of the Dormition (Sept–March 7.30am–12.30pm & 4.30–5.30pm; April–Aug 7.30am–noon, 5.30–6.30pm; free), which contains the town’s top art treasure: a painting of the Assumption by El Greco, executed while he was around 20 years old.

Vapória

Up from the right of Miaoúli square is the Apollon Theatre, built like an Italian provincial opera house, which occasionally hosts performances (during morning rehearsals you can enter and watch for free or visit its small museum for €1.50). Further on up, the handsome Neoclassical Orthodox church of Áyios Nikólaos was built in 1848–70, with an impressive marble iconostasis (7am–2pm & 5–8pm). Beyond it lies the Vapória district, where the island’s wealthiest shipowners, merchants and bankers built their mansions.

Áno Sýros

On the taller hill to the left from Miaoúli square is the intricate medieval quarter of Áno Sýros, with a clutch of Catholic churches below the cathedral of St George. Just below it lies the Capuchin monastery of St Jean, founded in 1535 to do duty as a poorhouse. Once up here it’s worth visiting the local art and rembétika exhibitions, as well as personal items of the man himself at the Markos Vamvakaris museum (June–Sept daily 11am–2pm & 7–10pm; €1.50).

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