Greek Islands (Cyclades)
Whitewashed villages, volcanic cliffs and water that really is that colour: the Cyclades are the Greece everyone pictures. The skill is choosing three islands that suit you and letting the ferry timetable shape the rest.
May–September lands in summer for Greek Islands (Cyclades): warm, sunny weather ideal for the coast; prime hiking and outdoor season with the trails and passes open; calm seas and swimmable water.
Choosing your islands
Santorini is the caldera, the sunsets at Oia and the wine grown in volcanic ash. It is stunning and it is crowded, so stay in Imerovigli or Pyrgos rather than Oia and see the famous view early in the morning.
Mykonos is the glamour and the nightlife, with beach clubs at Paradise and Super Paradise and prices to match. Naxos is the all-rounder: the biggest island, with long sandy beaches, mountain villages, decent food and much better value. Paros and its small neighbour Antiparos sit between the two in style and are the easiest hub for onward ferries.
For quieter trips, Milos has the lunar Sarakiniko rocks and 70-odd beaches, Folegandros and Sifnos are small, walkable and food-focused, and Amorgos and Koufonisia are as far from the crowds as the group gets. Delos, uninhabited and entirely archaeological, is a half-day trip from Mykonos and one of the great ancient sites in Greece.
A good first trip: Naxos, Paros and Santorini in ten days. A better second one: Milos, Sifnos and Folegandros.
How the ferries work
Almost everything runs from Piraeus in Athens, with some routes from Rafina, which is closer to the airport. Two speeds: slow, big and cheap car ferries, and fast catamarans that cost roughly double and cancel more readily in high wind.
Book ahead in July and August, especially with a car. Plan island order to follow one ferry line rather than criss-crossing, keep a buffer day before your flight home, and expect the meltemi, the strong summer north wind, to disrupt sailings for a day or two at a time in July and August.
Island-hopping flights exist to Santorini, Mykonos, Naxos and Milos, and are worth it if your time is short.
Beaches, food and evenings
Beaches range from the organised sunbed-and-cocktail sort to unmarked coves you reach on a dirt track. Standouts: Plaka and Sarakiniko on Milos, Plaka and Agios Prokopios on Naxos, Kolymbithres on Paros and the red and black volcanic sands of Santorini. Renting a car or an ATV for a day or two unlocks the best of them.
Eat at the taverna on the water: grilled octopus, fried courgette, tomato fritters from Santorini, fresh fish sold by weight, and whatever cheese the island makes. Sifnos is the accepted culinary capital of the group. Dinner starts late, from 21:00, and shops shut for the afternoon.
When to go and what it costs
May, June, September and early October are the best months: warm sea, full ferry schedules and manageable crowds. July and August bring the heat, the peak prices and the meltemi. From November to March many islands largely close down, with Santorini, Mykonos and Naxos keeping a skeleton service.
Costs vary hugely by island. Expect around €120-180 a day for two on Naxos or Milos, and half again or double that on Santorini and Mykonos in August. Cash still helps in the smallest villages.
If you like this shape of trip, the Ionian Islands guide covers the greener, calmer side of Greece.
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