Off-Season Greece: Fall in Santorini Through the Eyes of Winemaker Michael Kouloglou

Are there any areas of the island that really come alive during the off season?

As the summer venues close, the life of the island doesn’t disappear; it just shifts to the places where people actually live year-round. Areas like Karterados and Messaria become the real hubs. They are central points on the island that stay busy and full of life all year. The local closing parties of fall range from wild gatherings by the beach bars to more laid-back evenings in traditional cafés and small local hangouts. Later, in the winter, as people begin gathering more at homes, these central areas remain the heart of our social life.

But if you want to talk about a completely hidden side of Santorini that comes alive in a very quiet, spiritual way, it’s the Askitaria. These are old stone monk lodgings perched right on the edge of the cliff on the mountain between Perissa and Kamari. In the spring, you will find many locals sitting there for hours, doing nothing in particular but gazing out at the endless blue, the passing ships, and distant islands like Anafi, Ios, and Anydro.

Pezoulia Restaurant by Honeymoon Petra Villas in Imerovigli overlooks a quiet stretch of sea.

Giorgos Sfakianakis

How does the weather change the destination during this time of year, and what are the (dis)advantages of that?

Autumn and winter are much warmer and sunnier than most people expect. They bring a rare, beautiful peace. For us winemakers, even the rain is a blessing, not bad weather. It’s a relief to see the vines finally get a drink after months of summer drought. The main disadvantage—if you can call it that—is the unpredictability. March, for instance, is a strange and stubborn month with strong winds, cold snaps, and constant weather shifts.

What does a perfect Saturday in the off-season look like to you?