Best for: Culture and off-season cachet
While I often flit between many Greek islands when trying to pin down a favorite, I always seem to land back in Syros. Ask me why, and I’m unsure. I think it’s something to do with how authentically real it is, as well as its clashing-but-cohabiting mix of cultures. Everything here just works. It’s the capital of the Cyclades, and its main town, Ermoupoli, is the administrative center of the island group. This might all sound a bit boring, and perhaps not really relevant to your next Greek getaway, but it’s because of this that the island makes such an impression.
Syros cares less about tourism than other islands, instead offering a true glimpse into Greek island life away from the stereotypes. It’s got scale, too. The buildings here—a mix of Cycladic, Venetian, and Neoclassical architecture—are bigger than most, standing tall and proud along Ermoupoli’s coastline: there’s the imposing blue-domed but orange-fronted church of Agios Nikolaos; the impressive City Hall of Hermoupolis, built under the supervision of Ernst Ziller and with a 50-foot-high entrance staircase to rival that of any European capital; and the 19th-century Apollon Theater, designed as a replica of Milan’s La Scala. Towering behind them all is Ano Syros, almost 900 steps above Ermoupoli; reward yourself with dinner at Hygge, with views back to the main town. If you don’t fancy the hike, a taxi can drop you off at the door.
Then there’s the cultural scene, and Syros has plenty going on year-round. It’s home to art, music, cinema, and dance festivals that go on long into the autumn months, like the Syros Jazz Festival that takes place in September, and the International Music Festival from October 21st through the 24th. The beaches here don’t live up to those on its Cycladic neighbors, but Galissas, Delfini, and Agathopes are worth visiting for a few hours in the sun—and locals love Vaporia’s concrete slab, overhanging the sea and overlooking some of Greece’s finest Neoclassical mansions, for a quick dip. —K.S.
Where to stay in Syros:
