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.
