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Santorini in Winter: Where Our Travel Story Began

Our honeymoon in 2009 wasn’t just about Santorini’s sunsets — it was the start of our love for exploring the world quietly. Winter turned the island into our private postcard, teaching us that sometimes, less plan means more magic.

Back in December 2009, we were newly married, broke but bold, and hungry to see the world. One of my colleagues had just returned from Santorini, raving about the island’s charm and views that looked unreal even in photos. That planted the seed.

We wanted something different for our honeymoon. Somewhere far enough to feel like a dream, but still real enough to reach. The plan was simple: a short stop in Athens, then onwards to Santorini.

This was before the days of easy mobile data and travel apps. We had to print maps, guess bus routes, and hope our hotel bookings were real. All we knew from a few random websites was that Santorini in December would be quiet, most cliffside villas shut, and the island practically asleep for winter. We saw that as an opportunity.

Aegean Airlines took us there in a small Avro RJ100, the kind of regional jet that aviation geeks like me still remember fondly. The short flight out of Athens was smooth, the views over the Aegean were surreal, and when the island finally appeared beneath the clouds, it looked exactly like what we had imagined — white, calm, and timeless.

At the tiny airport, we were greeted by Andreas, our driver from Mill Houses, a small boutique hotel perched between Fira and Firostefani.

He turned out to be everything from driver to cook to all-round host. The hotel was quiet, with just a handful of guests. Winter had scared most tourists away, and that worked in our favour.

The moment we opened our room door, the view hit us. Whitewashed rooftops spilling down the cliffside, the deep blue caldera below, and not a sound except the wind and church bells in the distance. It was the kind of silence that makes you feel small, grateful, and alive.

Mornings were slow. Breakfast arrived on our terrace, served by Andreas himself, always with a smile and strong coffee. We had no plans, no itineraries, just a habit of walking until we were tired and stopping wherever the path led us. The shops were mostly shut, but that didn’t matter. We had the island to ourselves.

One afternoon, I rented a Smart ForTwo for 35 euros a day. My first experience driving on the other side of the road. We zipped along the narrow roads that wrapped around the island, occasionally stopping to take photos or just to admire the emptiness. Red Beach, Black Beach, the highest lookout points — all ours. It felt like the world had paused just for us.

Everyone who goes to Santorini talks about the sunset. They say it’s magical, and they’re not wrong. On our first evening, we followed the crowd’s advice, rushing to Oia hours before sunset to find a “good spot”. We stood there with dozens of others, cameras ready, waiting for the perfect moment. And it was beautiful, but it also felt a little forced.

The next day, we stayed back at the hotel and watched the sunset from our own terrace. That view, framed by our white walls and the quiet hum of the sea, was even better. No crowds, no pressure, just us and the fading light over the Aegean. That was the moment we realised that travel isn’t about chasing what others call perfect. It’s about finding your own version of it.

Santorini taught us how to travel differently. It taught us to beat the crowd, to appreciate quiet, and to let go of rigid plans. It also reminded us how vast and beautiful this world is, and how lucky we were to share it together.

Fifteen years later, I still think about that trip. About the empty paths, the cold breeze, and how that week shaped the way we travel today. I don’t know what Santorini looks like now. Maybe it’s crowded, polished, and full of selfie sticks. But I’m glad we saw it when we did. That winter, the island belonged to us, and we belonged to the moment.

That, to me, is what travel is all about.

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