The caldera is still magnificent. The trick is knowing which week to arrive — and which village to skip entirely.
Santorini has, over the last decade, become a victim of its own photograph. The blue-domed church of Oia is now reached by a queue. The sunset that made the island famous is, in July and August, watched by a crowd of several thousand. None of which means the island is no longer worth going to. It means going at the wrong time is no longer worth going at all.
This is a guide to the right time, the right villages, and the suite-level houses that still deliver the Santorini you came for.
Go in September. Go in the second half of September.
The cruise season tapers in mid-September. The water remains warm — 23 degrees through the first week of October — and the meltemi wind softens. The light, in late September, is the light that the painters came for: long, low, and the colour of unfiltered honey on the white walls of Imerovigli.
Stay in Imerovigli, not Oia.
Oia is the village in the photographs. Imerovigli is the village two kilometres north, two hundred metres higher, and an order of magnitude quieter. The view of the caldera is, if anything, better. The walk to Oia for sunset takes thirty minutes along the cliff path — which is, itself, the best walk on the island.
Where to stay
Canaves Oia Suites remains the most architecturally considered property on the island, and we still book it often — but we usually route our travellers to its sister property, Canaves Epitome, set just below the village. For the wellness-led, Mystique on the Oia ridge is the most contemplative house on the cliff. For the romantics, Grace Hotel in Imerovigli is the suite we book for honeymoons more than any other on the island.
What to do that is not the sunset
Charter a private catamaran from Vlychada — not Ammoudi — and circle the caldera with a stop at the Red Beach and the warm springs at Palea Kameni. Hire a private guide for the archaeological site at Akrotiri, which is the Pompeii most travellers have never heard of. Eat dinner at Selene in Pyrgos, which has been the best restaurant on the island for thirty years and remains so.
How long to stay
Four nights. Three feels rushed; five begins to feel long unless you are pairing the island with a charter through the Cyclades. Most of our travellers combine Santorini with three nights in Mykonos or, increasingly, with a week aboard a private yacht through Folegandros, Milos and Sifnos — the islands that Santorini used to be.
Where to stay
Book the houses from this story
