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Gregale

The Cyclades — the well-known ones

The islands everyone pictures when they picture Greece: white cubes, black rock, a sea that reads almost purple at midday. They are busy, and they are still extraordinary — the whole game is timing.

  • Whitewashed Cycladic village on cliffs above a still Aegean sea at first light
    Santorini, before the ships
  • A narrow whitewashed lane with bougainvillea in a Cycladic chora
    Naxos Chora
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The character of the place

The classic Cyclades are the most photographed landscape in the Mediterranean, and the photographs are not lying. Santorini's caldera really is a drowned volcano with towns balanced on its rim. Paros and Naxos really do have marble villages, working farms and beaches that run for kilometres.

What the photographs leave out is scale of traffic. In July and August Santorini can take five cruise ships in a day, and Oia at sunset is a crowd, not a view. The fix is not to avoid these islands — it is to be on them at seven in the morning and at eight in the evening, and to be somewhere else at noon.

Naxos is the one to know about. It is the largest and most self-sufficient of the group, with a mountain interior, real agriculture, cheese and citron of its own, and long empty sand on the west coast even in August. It absorbs visitors in a way Santorini cannot.

Worth the day

  • The caldera by boat, not by road

    A private caïque out to the volcanic islets and the hot springs, leaving mid-afternoon and back for sunset on the water.

  • Assyrtiko in the vineyard

    Basket-trained vines lying flat in volcanic ash, tasted in a cellar with the person who made it.

  • Delos

    An entire uninhabited sacred island, thirty minutes off Mykonos. The most complete ancient city you can walk through in Greece.

  • Inland Naxos

    Marble villages, a Venetian tower, an emery mine, a kouros lying unfinished in a field where it cracked.

Where to base yourself

  • Imerovigli or Pyrgos, Santorini

    Caldera views without Oia's crowd flow; Pyrgos is inland, higher and quieter.

  • Naxos Chora or the Tragaea valley

    Port-town life, or olive groves and Byzantine chapels twenty minutes inland.

  • Naoussa, Paros

    A working fishing harbour that turned into the best-eating town in the Cyclades.

What to skip

Oia at sunset in August, and any beach club advertising a DJ. Both are avoidable without losing anything.

Three ways this region is travelled

Worked examples, not products. Each opens day by day, with the route drawn on a map.

7 days · Late May – early October

Caldera, then the marble island

  1. Athens
  2. Santorini — Imerovigli
  3. Naxos Chora
  4. Tragaea valley
  5. Athens

Three nights of caldera light, then the largest and most self-sufficient of the Cyclades to slow the pace down. One ferry, no rushing.

Day by day, on the map

6 days · May – June, September – October

Naoussa's kitchen and the Paros coast

  1. Athens
  2. Naoussa, Paros
  3. Lefkes
  4. Naoussa

A single-island week built around a fishing harbour that has become the best-eating town in the Cyclades, with one inland night to see the marble villages behind it.

Day by day, on the map

5 days · May – June, September

Mykonos at the edges, and Delos

  1. Athens
  2. Mykonos Chora
  3. Delos
  4. Ano Mera
  5. Mykonos Chora

A short, deliberately narrow trip: Mykonos handled at its quieter hours, with a full day given to the uninhabited sacred island thirty minutes offshore.

Day by day, on the map

Pairs well with

  • Athens & Argo-Saronic

    Athens is the gateway anyway — give it two nights rather than a transfer.

  • Cyclades (off-grid)

    Two days of the famous ones, five of the quiet ones. The best-balanced Cycladic week there is.

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