Best Greek island for: Culture and off-season cachet.
On Syros, capital of the Cyclades, you won’t find sugar-cube villages and whitewashed lanes. The colourful 19th-century city of Ermoupoli is built on twin peaks – one Orthodox, the other Catholic, the heritage of a long Venetian occupation. There’s still a strong Italian flavour in Ermoupoli’s marble piazzas, princely mansions, and miniature replica of La Scala, the showpiece of a year-round cultural scene.
If there’s a common word that describes the hotels of the Greek islands, it’s 'epic'. The stereotype of a Greek island guest room is practically legendary: whitewashed walls, cave-like forms, and impossible views from cliffs overhanging the sea. It’s one of the better formulas you’ll find anywhere and, like the sirens of Greek mythology, it’s an irresistible scene that has attracted travelers for decades.