My Favorite Airbnb: A Hilltop Hideaway on an Underrated Greek Island

Whenever I’m lucky enough to set my eyes on an expanse of blue, I feel the need to stare at it for as long as I can, hoping that my brain will somehow snap a picture and cement it in my memory forever. That’s exactly what I did every sunrise and sunset at this hilltop hideaway in Andros, a highly underrated Greek island just an hour away by ferry from Athens.

When I started planning my summer trip, I knew I wanted to go somewhere in Greece, a place I’d be returning to after unforgettable trips to Mykonos and Milos. This time, the Airbnb came before the island. At Condé Nast Traveler, I spend a lot of time scouting exceptional rental properties (tough job, but someone has to do it). When I stumbled upon the Aegean-blue vista from both bedrooms of host Dimitris’s Cycladic oasis, I phoned up my best friend Claire and booked it immediately.

Andros, it came as no surprise, was wildly beautiful, an island that seemed to be visited by more Greeks than international tourists. It’s green and mountainous and populated with a lot of sheep. Renting a car is easy (shout-out to Escape in Andros), but getting around requires a little extra verve, as many roads are winding, rocky, and cliffside—especially if you, like me, are interested in exploring the more rugged, far-off beaches.

It’s safe to say I held my breath as Claire courageously drove us up to our rental, located in the Kalamaki settlement of Andros. But by the end of our stay, I got used to the ritual, focusing my attention instead on the arresting views unfolding beyond our windshield. I’ve been traveling long enough to know that the hardest-to-reach places are often the most beautiful, and here we were, friction-maxxing.

When Dimitris showed Claire and me around the property, we felt struck by the sublime. There was the sea, front and center, its horizon almost indistinguishable from the cloudless sky. We took it in from the patio, which was shaded by an imposing carob tree, an ingredient we’d see make its way into the island’s Greek salads as crunchy rusks.

There was no shortage of lounge spots to choose from

This was our view, one late afternoon—casual!