A white lighthouse at the tip of a long rocky headland near Korissia on Kea, lit gold by the low sun.

Trips · Greece

Greek islands, cities, monasteries and more.

Two or three days in Athens, six Cycladic islands by sailboat, and two nights among the monasteries of Meteora.

Why go

Greece is much more than its islands.

Start in Athens, and give it more than a night on the way to the ferry. The Acropolis and the Parthenon are the reason everyone comes, and the Acropolis Museum below them is one of the best in Europe. Then there’s the old town of Plaka, the ancient Agora, the view from Lycabettus Hill at sunset, and dinner on a rooftop with the Parthenon lit up across the city. Few capitals put 2,500 years of history this close to a good meal.

Then the islands. Six of them from the deck of a sailboat: one cabin, no repacking, and a different harbor every morning.

And then Meteora, which might be the most surprising place in Greece. Monks began building monasteries on top of its sandstone pillars in the 14th century, hundreds of meters above the valley, and six of them are still active today. It’s a UNESCO World Heritage Site. Photos don’t quite explain it.

The route

  1. Athens · the Acropolis, Plaka and the Acropolis Museum
  2. Kythnos · Dryopida
  3. Kimolos
  4. Folegandros
  5. Paros · Naoussa
  6. Syros · Ermoupoli
  7. Kea · Korissia
  8. Back to Athens · then north to Meteora, about 4 to 5 hours by train or car
  9. Meteora · 2 nights · Kastraki and Kalabaka
  10. Athens · fly home

Two or three days in Athens in all, split between the start and the end of the sailing trip. Want Mykonos or Santorini as well? Both are easy to add from Athens, by ferry or a short flight.

What we’d skip

  • Santorini in peak season, especially on days when cruise ships are docking. The caldera is still worth it; pick shoulder season, or stay overnight and go early.

Best time to go

  • Late May and June. Warm days, long evenings and fewer people than high summer. The sea is still warming up.
  • July and August. The hottest and busiest months, with the highest prices. The meltemi, the strong northerly wind of the Aegean, usually blows hardest now, which matters on a sailboat.
  • September to mid-October. The sea is at its warmest, the crowds thin out and the meltemi usually eases.
  • November to April. Many island hotels and restaurants close and ferries run less often. A good time for Athens and Meteora on their own.

We love going in September, for the smaller crowds and the perfect weather.

A deep blue cove on Folegandros with three sailboats at anchor below dry brown hills.
Folegandros.
Ceci in a pink top standing in a whitewashed courtyard under bright pink bougainvillea on Folegandros.
Folegandros.
Looking up at a white sail against a deep blue sky, under way between the Cyclades.
Under sail, off Kythnos.
The view from a shaded waterfront terrace across the water to the white houses of Kimolos.
Kimolos, from the terrace.
Kimolos harbor in evening light, an inflatable tender in the foreground and white houses along the shore.
Kimolos harbor.
Ceci and Scott taking a selfie in sunglasses, with the golden sea cliffs of Folegandros behind them.
Folegandros.
Ceci in a white dress on the steps of a white church in Naoussa, Paros.
Naoussa, Paros.
Naoussa's old harbor on Paros at night, tavernas lit along the water with small boats moored in front.
Naoussa harbor, after dark.
Ceci standing on the rocks at Meteora in golden evening light, cliffs and valley behind her.
Meteora.
The sandstone pillars of Meteora at sunset, the sun breaking over the ridge above a green valley.
Meteora.
The row of windmills above Mykonos town at dusk, lit warm against a blue sky.
Mykonos.
A blue-domed church and white houses on the cliff edge in Oia, Santorini, above the caldera.
Oia, Santorini.
Ceci leaning on a white wall above the caldera cliffs in Oia, Santorini.
Oia, Santorini.
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