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Five Trips to the Greek Islands. Here’s What I Know Now.

Posted on March 1, 2026 by

First trip: Santorini, because of course. Second trip: Mykonos, same reason. Third trip I finally listened to someone who’d been more than twice and went to Milos instead. That’s when it actually got interesting.

Milos is what people think Santorini is

The volcanic rock formations at Sarakiniko look genuinely lunar — white, smooth, sculpted into arches and natural pools by centuries of wind and sea. There were maybe twenty people there on a summer afternoon. Twenty. In the same week the caldera view in Santorini had a literal queue to take a photo. Milos has the same wild Aegean beauty with none of the machinery built up around it.

Naxos will feed you

The largest and most fertile island in the Cyclades, and the food absolutely shows it. The local potatoes are famous across Greece. The graviera cheese is made from goat milk from hillside animals and you can taste exactly that. The citron liqueur called kitron is unique to Naxos — bring a bottle home. I gained three kilos in four days and felt nothing but grateful.

The thing that changed how I travel here

Slow ferries instead of fast catamarans. Yes it takes longer. But you sit on deck with a coffee and watch the islands appear and disappear on the horizon one by one. You talk to people. You arrive in a place gradually rather than being deposited into it. The journey is part of what you’re doing out here, not the obstacle between the things you’re doing. Greece keeps trying to teach me that. I’m finally starting to listen.

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