Places to Stay

Could a hilltop hideaway be better than a beachfront retreat on a family trip to a Greek island?

VILLA DE VIENTO

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2-Bedrooms | From €350 per night

Quite possibly. Especially if the kids have outgrown their toddler years.  And particularly in Milos, where an eccentric coastline of rockscapes has limited beach hotels and villas from sprouting up on every seaside parcel of land.

Looking out into haunting sea views, the church steeples of Agios Nikolaos float quietly in a far corner. Villa de Viento occupies a hilltop position of rare privilege, where beauty and history intertwine. Scattered across the surrounding slopes of Trypiti are the Hellenistic theatre, the early Christian catacombs, and the place where the Venus de Milo lay hidden for centuries. Together, they lend these beautiful grounds an almost mystical atmosphere.

THE SPACE

Set within an olive grove, with a row of traditional windmills punctuating its edge, the two-bedroom villa is spacious, light-filled and impeccably maintained. So clean, I freely enjoy walking around bare-footed as is our Asian custom at home. Inside, the atmosphere is unmistakably Greek. Hand-painted wooden cupboards adorned with floral motifs, a country-style kitchen, an antique sewing machine repurposed as a table, and even a piano lend the villa the warmth of a much-loved family home. French doors frame arresting views across the surrounding landscape, inviting the outside in at every turn.

YOUR HOSTS

Nikos and Katerina have considered every need in equipping the property. From cooking implements, next-day breakfast essentials, a Nespresso machine, orange juicer, beach toys, extra linen…all is as complete as guided by Greek hospitality. Not the tourist-savvy kind of trained hospitality, but heartfelt acts of care that are spontaneous, surprising, and an impetus to returning.

One afternoon, while the girls chase cats outside as they do for hours, Katerina invites them to join her making cheese pies. D is thrilled, but little A isn’t as keen, so Nikos takes her for a walk in the garden. Another evening, we find the best kind of surprise in our fridge after a long day out – homemade Sokolatopita (a Greek “chocolate pie”, but more akin to a cake). A knock-out version of the divine local dessert surprisingly few foreigners are acquainted with. And before we leave, Nikos gives the girls a precious sack of “eye of Naxos” shells. They leave longing to return to this special abode of treasures and loving warmth.

There is no cot available on the property. With a short bout of internal stairs taking you from living room to raised sleeping quarters, the villa is better suited for children of more than 3 years of age.

THE NEIGHBOURHOOD

While this mountain village experience departs from my usual preference for a beachfront retreat, tranquil Trypiti has heaps going for it. It may not be teeming with village life, but steps from the villa is a selection of key family conveniences: A coffee stop, a pizza and pasta essential for picky eaters, and the newly opened OKTO for an indulgent night out. Farther down where the slope meets the sea, Astakas Kilma is our favourite restaurant on the island for family dining. And a 5-minute drive away is Plaka. The only traditional village of significant size, here you can experience that idyllic Greek island dream of wandering through a tangle of blue and white village alleyways to shop, wine and dine late into the Mediterranean night.

Sleeps: Four. Two bedrooms have double beds in each (although one of the double beds is slightly smaller than the standard).

Spend: From about €350 per night in summer.

Every once in a while, you find that special place that meets the impossible set of criteria that makes families exceedingly happy. We found just that within the hustle of downtown Athens, nestled in an oasis of preternatural calm.

THE AEOLIAN

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3 Bedrooms | From €200 per night, depending on the season

In the concrete ugliness (truth be told) of Athens’ city center, historical Plaka is an alcove of charm. And within Plaka, the Aeolian’s location is unmatched. A stone’s throw across the street, the 1st century BC Roman Agora fills your living room windows, while bedrooms face a leafy green square with a view towards the Acropolis.

If you’re familiar with downtown Athens, you’ll know just how special this spot is. Not just for its graphic surroundings. It’s also strategically close to everything a family might need. All within an easy five-minute walk are: an AB supermarket, Starbucks (or Third Place if you’re serious about coffee), Ermou (the Champs-Élysées of Athens), Monastiraki train station and taxi stand (opposite Moustakas toy shop), and on the stretch of Adrianou pedestrian street opposite the Stoa of Attalos, a line of tavernas (not all too touristy – try Kuzina) and cafés look out into an ancient park peppered with monuments. The Acropolis Museum is also a 12-minute walk away. With little feet to herd around, this location is everything. 

Sleeps: Six (Three-bedrooms)

Two, generously-sized three-bedroom apartment units have double beds dressed in crisp white linen. And two bathrooms in each apartment mean relaxed family bath times. Cots are available on request.

Vibe: With herringbone parquet floors bathed in light streaming in from French windows, there’s a feeling of lightness in the open-plan space. Velvety soft mid-century style furniture lend a stylish warmth to modern interiors, while a sleek kitchen and gleaming marble toilets highlight the update to the neoclassical townhouse. Move the glass vase ornaments aside and the living room is spacious enough for the kids to play balloon volleyball in . Need a verandah? Pick the penthouse unit.

Notable Amenities: Netflix, a washing machine (laundry pods, a drying rack and iron included), air-conditioning (critical in summer, and not always a standard in Greece), and a fully-equipped kitchen for assembling easy breakfasts, entertaining snack requests on repeat, and preparing quick meals. We find that it’s easier to feed kids at home, so dinner orders from efood.gr were frequent. There’s no parking lot allocation, but we don’t advise driving around the chaos of town anyways.

The Service: Attentive and responsive.

Price: From about €200 per night in winter.

The Neighbourhood (within a five-minute walk):