In short: choose Santorini for the caldera views, Crete for variety, Paros or Naxos for a well-balanced family trip, and Sifnos for food and peace and quiet. For a first trip of around ten days, the best approach is to combine two or three Cycladic islands linked by ferry, starting in Athens. The best months are late May, June and September: warm sea, soft light and far fewer people than in July and August.
The Greek islands at a glance
| Island | Ideal for | Highlights |
|---|---|---|
| Santorini | Honeymoons, first-time visitors | White villages perched on the caldera, sunsets, volcanic wines |
| Crete | Active travellers, stays of more than a week | Minoan palace of Knossos, Samaria Gorge, beaches and mountain villages |
| Paros | Families, a first taste of the Cyclades | Fishing villages, varied beaches, easy connections to other islands |
| Naxos | Families, hiking | Largest island in the Cyclades, long sandy beaches, inland villages |
| Sifnos | Food lovers, travellers seeking calm | Culinary tradition, pottery, trails between chapels |
Santorini: for the caldera
Santorini owes its landscape to a major volcanic eruption around 3,600 years ago, which left a vast caldera ringed by cliffs. The villages of Oia and Fira, perched on its rim, offer some of the most famous sunsets in the Mediterranean — and therefore heavy crowds in summer. Two or three nights are usually enough to enjoy the caldera, the vineyards and the volcanic-sand beaches before moving on to a quieter island.
Crete: for variety
Greece's largest island, Crete is almost a country in its own right: the Minoan palace of Knossos near Heraklion, the Venetian lanes of Chania, and the Samaria Gorge, one of the longest in Europe at around 16 kilometres of walking, usually open from May to October. It deserves at least a week, as on our Crete journey.
Paros, Naxos and Sifnos: for the rhythm of the Cyclades
Paros and Naxos, neighbours with good ferry links, suit families perfectly: sheltered beaches, lively but never overwhelming villages, and plenty of water sports. Sifnos, more discreet, is known for its cooking and its potters, and is best explored on foot between white chapels and terraces. Our Athens, Sifnos, Paros and Santorini journey links exactly these islands, showing three very different sides of the Cyclades in a single trip.
When to go to the Greek islands
The season runs from May to October. In July and August, the meltemi, a steady northerly wind, often blows hard across the Cyclades: it cools the air but can make the sea rough and disrupt some ferries. Late May, June and September offer the best of both worlds, with a sea that is already or still warm — it usually reaches its highest temperatures in late August and September. Crete, further south, enjoys a slightly longer season.
How many islands to combine?
Allow three to four nights per island to enjoy them without spending your days in ports: two islands for a week, three for ten to fourteen days, plus one or two nights in Athens. To hop between islands without ferry timetables, a small-ship cruise is a lovely alternative, like our Aegean cruise. For a first visit, our Athens, Meteora and Santorini itinerary pairs the Acropolis, the cliff-top monasteries and the caldera. See all our trips to Greece, or tell us what appeals to you: within 24 hours we'll suggest the combination of islands that suits you.