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Planning an island-hopping trip to Greece in the summer isn’t easy. Make it a family trip in the peak month of July and the task becomes, ahem, near Herculean. I knew when I started sketching out the trip that I wanted to spend a few days in Athens to show my kids, then 18 and 15 years old, and my husband, who had never been to Greece, the capital city’s museums, archaeological sights, and excellent food scene, followed by a few days on two different islands where we’d explore the little towns, swim in the Med, and eat our weight in fresh seafood and Greek salads. I landed on two islands in the Cyclades: Sifnos, which is super laidback, not very touristy, and becoming increasingly known for its food and wine, and Milos, which, while still very chill when compared with islands like Santorini and Mykonos, has a bit more going on for teenagers—and has, in my opinion, some of the best swimming beaches in Greece. I also knew that I didn’t want to stay exclusively in hotels because given my kids’ ages this usually means two hotel rooms, which gets pricey and always seems to limit unstructured family hang time.
I decided that renting a house on Milos, our last stop, was the way to go. I figured that by day eight, the kids would be ready for their own bedrooms and I’d be ready for breakfasts that didn’t require putting on shoes or paying buffet prices for fruit and coffee. I started poking around Airbnbs on Milos and when I saw this three-bedroom house in the cliffside side town of Plaka, located on the northwestern part of the island, I’m pretty sure I squealed out loud. The house’s epic, unobstructed 270-degree views out over the Bay of Adamantas are what initially hooked me. And while the listing photos of the interiors looked nice, they in no way did justice to how beautifully designed and meticulously decorated the house was in person—and just how stunning the location turned out to be. In our age of filters and fisheye lenses, this sort of “better in person than in photos” experience was a delightful first for me!
We took an hour-long ferry from Sifnos to Milos’s bustling port town of Adamantas where we picked up our rental car. You can take the public bus from town to town, but if you want more flexibility or to visit more deserted spots and tucked-away beaches, definitely get a car. We drove for about 20 minutes and parked the car in a reserved parking spot in a gated lot just outside of town that our Airbnb hosts had specified in earlier communications (the hosts were extremely communicative, helpful, and reachable throughout our stay). There are no cars allowed in the town, which is a maze of stone alleyways lined with whitewashed houses built in the traditional Cycladic style, cafés and restaurants, and little shops. It has to be one of the most charming towns I’ve ever visited—touristy, but in a fun, lively way and not an annoying, overrun way—even during high season. We rolled our suitcases past people having pre-dinner drinks at outdoor tables that spilled into the narrow streets and those gathering—as is the evening ritual—in the mosaic-tiled courtyard of the Panagia Korfiatissa Church to watch the sun set over the Aegean. Our Airbnb was just a few houses past the church.
We unlocked a sky-blue door that opened onto a flagstone-paved courtyard punctuated with a few decorative amphorae and baskets. Heading through the main door (there are two other patio doors that lead into one of the bedrooms and the living room) we found ourselves in the kitchen of my dreams, with stone floors, tons of counter space, and a dropped marble sink where, when you did dishes, you had views of the sea. The kitchen was well-stocked with beautiful dishes and a station with about five different machines and means for brewing coffee (I ordered several items I used during my stay for my kitchen back home). The faces of the kitchen cabinets—as well as the window trim and door frames throughout the house—are that same pale blue that contrasts so beautifully with the white plaster walls. The kitchen, and the living room—which is a marvelous mix of midcentury-modern decor (Børge Mogensen chairs, pendant light fixtures), antiques, and more rustic touches, like wood-beamed ceilings and wide-planked floors—open onto a large outdoor terrace with a table where we had breakfast every morning, happy hour every evening, and watched the sun set over the water before heading out to dinner. Two of the bedrooms—simply decorated but extremely comfortable and with nice beds and bedding—and two bathrooms are on the main floor. The third bedroom and a smaller bathroom are downstairs (the stairs are pretty steep and might be tricky for small children or anyone with mobility issues). From every window, you catch at least some glimmer of the sea below.
We quickly fell into a routine where the kids would walk down the street to Cafe Palaios and grab a few pastries (they made friends with the teens who worked there) and then we’d have coffee; flaky, custard-filled bougatsa; and watermelon pie (a Milos special—think fruit-filled pastry rather than a slice of pie) at home, before heading out to explore a different beach and part of the island. One day, we rented a small motorboat from Asterios Boat Rentals on the southern side of the island, and my husband ferried us around to empty coves and deserted beaches that we swam to from the boat. Another day we went to Paleochori Beach, also on the southern coast (the south is your best bet when the Meletemi winds are blowing), and then returned to Plaka to shop around and visit the little archaeological museum there. This Airbnb was a perfect jumping-off point to explore Milos, and we were always so happy to return to this bright, beautiful spot we got to call home for four days.
