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! The two whitewashed bedrooms were self-contained, each with its own bathroom, minimally decorated with an antique or two—no try-hard, boho crochet or one-too-many evil eyes in sight. Navigating around the property meant spending most of our time outside (a joy, really), where we bopped from one lounge area to another and enjoyed meals in the full, outdoor kitchen—complete with a brick oven, hot plate, and refrigerator.Dimitris permitted us to pick whatever we wanted from his garden, and every morning at breakfast we’d enjoy our fresh tomatoes, as well as some sesame bread, Greek yogurt, and sweet-as-sugar apricots purchased from the nearby port town of Gavrio. There, on the sea-facing dining table, we’d discuss our day’s plans as the cicadas chirped away. Perhaps our favorite feature of this Airbnb, though, was the semi-private beach we shared with a neighboring property (another one of Dimitris’s, better suited for a larger group), which we accessed from a short, downhill trail marked by rocks.It was a perfect little cove, surrounded by marble-esque rocks, the calm water somehow impervious to the island’s strong winds. And we didn’t have to worry about bringing sand into the nooks and crannies of all our things, because there was a lovely housekeeper named Chara who stopped by to clean our rooms every day. The Blue Mind Theory is true—being near water really does calm the brain—and I am its number one proponent.There’s this casual magnificence the Greeks are so good at—the way they can throw a fish on a grill, dress it with a little lemon juice, and present you with the freshest dinner you’ve ever had like it’s no big deal. And similarly, everything in this Airbnb made the ordinary feel like the extraordinary: taking a phone call while staring at the Aegean felt like the most romantic thing I’d ever done; stepping out of the shower, I spotted a dolphin from my bedroom window, alerting Claire like my life depended on it.It was always a tough call in the mornings, when Claire and I debated whether we’d want to stay put on the patio, or chase our vitamin D elsewhere. We couldn’t resist the allure of Achla, an unspoilt beach (celebrated as one of Greece’s most beautiful) hidden at the end of a very steep, rocky drive. Waiting for us was a pair of mystical swans, surfing the cove’s gentle waves.I'll never stop thinking about this moment at Achla Beach My room was dressed in white, with hints of blue from the sea For lunch that day we went to Aegean Balcony, a homestyle restaurant not far from our Airbnb, where we ate souvlaki and gazed at the most breathtaking view of Andros’s western coastline (there’s that casual magnificence thing again). We spent most of our nights wandering around the capital of Chora, a marble-lined city from which you can spot the storybook Tourlitis Lighthouse.All things considered, you could spend a few days on the property without ever feeling the need to leave. My adventurous side always does get the best of me, but if we had one more day, we’d spend the entirety of it right there, lazing away on our little beach.More of our editors' favorite Airbnb stays: