Complete Guide to the Cyclades Islands

Scattered across the heart of the Aegean, the Cyclades are the islands most travellers picture when they dream of Greece: cube-shaped white houses stacked above blue-domed churches, windmills standing on bare ridges, and little harbours where fishing boats rock in the wake of an arriving ferry. The group takes its name from the ancient idea that the islands form a circle, a kyklos, around the sacred island of Delos, and that sense of a close-knit family of islands still shapes the way you travel here. No two Cyclades are alike, yet they sit near enough to one another that moving between them is half the joy of the trip.

Nearly every Cycladic journey begins on the mainland. The two gateways are Piraeus, the great port of Athens, and Rafina, a smaller harbour on the eastern side of Attica that is especially handy if you land at Athens International Airport. Piraeus offers the widest choice of routes, with big conventional ships and fast catamarans fanning out across the archipelago, while Rafina is the traditional springboard for Mykonos, Tinos and Andros. Familiar operators on these waters include Blue Star Ferries, SeaJets, Fast Ferries and Golden Star Ferries, and during the warmer months the main islands enjoy frequent, often daily, connections.

Mykonos is the extrovert of the family. Its Chora is a maze of whitewashed lanes originally designed to confuse pirates, now filled with galleries, cocktail bars and boutiques, while the seafront quarter of Little Venice and the row of hilltop windmills provide the classic photographs. The southern coast is lined with organised beaches running from family-friendly to full-on party, and the island's nightlife needs no introduction. Yet Mykonos also guards a quieter treasure: the archaeological site of Delos, one of the most important sanctuaries of the ancient world, reachable by excursion boat from the old port and well worth setting aside a morning for.

Santorini is the one island that genuinely looks better in person than in photographs. The villages of Fira, Imerovigli and Oia cling to the rim of a volcanic caldera, hundreds of metres above a flooded crater, and sailing into the bay by ferry is one of the great arrivals in the Mediterranean. Beyond the sunset crowds you will find black and red sand beaches, the prehistoric town of Akrotiri preserved under volcanic ash, and vineyards producing crisp Assyrtiko wines from vines coiled low against the wind. Santorini is busy for good reason; visiting outside midsummer, or basing yourself in a quieter village, softens the crowds considerably.

Paros and Naxos, sitting side by side in the centre of the archipelago, are the heart of Cycladic island hopping and two of its most rewarding stops. Paros pairs the lively fishing harbour of Naoussa with the marble lanes of Parikia and a coastline made for swimming and windsurfing, and its central position makes it a natural crossroads of the ferry network. Naxos, the largest of the Cyclades, is a small world of its own: the marble gate of the Portara above the port, long sandy beaches such as Plaka and Agios Prokopios, and a mountainous interior of villages where the local potatoes, cheeses and citron liqueur are reason enough to visit.

Milos is the geologist's Cyclade, an old volcano whose eruptions left a coastline unlike anywhere else in Greece. The white moonscape of Sarakiniko, the pirate coves of Kleftiko and dozens of beaches in improbable colours draw boat trips all summer long, while tiny fishing hamlets like Klima line the water with brightly painted boathouses cut straight into the rock. The island where the Venus de Milo was discovered is no longer a secret, but it still feels a step gentler than Mykonos or Santorini.

Two more islands deserve a place on any shortlist. Ios balances its famous nightlife with a photogenic hilltop Chora, long golden beaches such as Mylopotas and a surprisingly peaceful character outside the peak weeks. Tinos, its neighbour to the north, is best known to Greeks as a place of pilgrimage: the church of Panagia Evangelistria draws the faithful all year round, and around August 15, the feast of the Virgin Mary, both the island and the ferries serving it fill to capacity. Beyond the sanctuary lie marble-carving villages, elaborate dovecotes and one of the most admired food scenes in the Aegean.

Planning an itinerary is mostly a matter of restraint. With seven to ten days you can comfortably enjoy three or four islands; try to squeeze in more and you will spend your holiday on gangways. A classic loop pairs a big name with quieter neighbours, for example Mykonos, Paros and Naxos, or Santorini, Ios and Milos. Crossings between neighbouring Cyclades are short, often under an hour on the fast boats, so travel days need not swallow the trip. Arrange your route so that your final island has a direct connection back to Piraeus or Rafina, and avoid booking a flight home on the same day as your last crossing.

A few practicalities make the difference between a smooth trip and a stressful one. In July and August the meltemi, a dry northerly wind, sweeps across the Aegean; large conventional ferries handle it comfortably, but smaller high-speed craft feel the swell more and are occasionally delayed, so travellers prone to seasickness may prefer the bigger ships. Book tickets well ahead for August, around the August 15 holiday and over Greek Easter, when seats, cabins and car deck spaces sell out. On the day of departure check that your sailing is running to plan, arrive at the port early, and keep your booking details to hand.

As for timing, the islands are at their sweetest in late spring and early autumn, when the sea is warm, the light is soft and the harbours are lively without being overwhelmed. Midsummer brings guaranteed sunshine and the fullest ferry schedules, at the price of crowds and wind. Whenever you go, resist the temptation to treat the Cyclades as a checklist. The archipelago rewards slow travel: an unhurried breakfast in a harbour cafe, a swim before the day boats arrive and the sight of the evening ferry gliding into the bay will stay with you as long as any famous sunset.