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. Syros hosts festivals of animation, dance, digital art, film, classical music, jazz and rembetiko, the Greek blues popularised by local musician Markos Vamvakaris. A few rembetiko joints have survived in the upper town, Ano Syra.
Sifnos owes its foodie reputation to its most famous descendant, Nicholas Tselementes, who wrote the first Greek cookbook in 1910. Forget souvlaki and moussaka: here, chickpea croquettes and stewed capers are taverna staples. The island is peppered with potteries that produce the earthenware casseroles used for revitháda (baked chickpeas) and mastello (lamb with red wine and dill). Traditional dishes are slow-roasted in a wood-fired oven at To Meraki tou Manoli, a local institution on sheltered Vathy bay. (While you’re there, invest in some timeless tableware from Atsonios pottery, in business since 1870.)
The almighty church has kept nightlife in check. If you must see and be seen, head to quietly glamorous Astivi or Stoa bar, on miniature Agia Lesvias square, in Hora. Beach life is generally languid and low-key; Psili Ammos and Livadi Geranou are our favourite hideouts. Dinner reservations are essential at Benetos, for Med-Asian fusion on an organic farm, and Lambi for grilled fish on a purple pebble beach.