Santorini’s Subterranean Dream: A Stay Inside Oia’s Luxury Cave Villas

There’s a particular kind of silence that falls when you open your door in the early hours and find yourself suspended above the sea, coffee in hand, the Aegean still inky and asleep, where the hum of anticipation for sunset hasn’t yet begun, and the only thing stirring is the steam rising from your private infinity jacuzzi.

This is not a dream. It’s Santorini. And you’re staying in a cave.

The yposkafa (literally “dug into rock”) are the island’s original dwellings. Once homes for sailors too poor to build on the land above, these carved-out hideaways are now the crown jewel of luxury accommodation in Santorini. You’ve seen them on every travel magazine cover: white, impossibly smooth, clinging to the volcanic cliffs like sculpture. But behind the filtered façade lies a story less glossy, overshadowed by the ambitions of travellers seeking the ultimate luxury holiday.

Born out of necessity rather than aesthetics, these cave houses kept seafarers cool in the scorching summer and warm in the bite of the off-season wind. They carved their dwellings into the rock, unknowingly setting the foundations of what would go on to make the island so coveted. Many sailors lived in Oia, by the old shipping wharf, hence, Oia has the largest number of cave villas on the island. They were practical, modest, and hidden. The Cycladic version of underdog architecture.

This is Greece, but tragedy doesn’t stick around for long; what once signified survival is now the stuff of five-star fantasies. The cave houses would be almost unrecognisable to the impoverished sailors who found a humble place to live. Come to the popular, blue-domed village of Oia, the more mellow Imerovigli and the capital, Fira, and you will see the caves transformed into plush modern suites, with caldera views and infinity pools. Once a symbol of low-status, staying in a cave house is now a marker of a chunky disposable income. It’s is a classical story of how Santorini has managed to turn misfortune on its head once again.

Checking Into the Cliffside

I was invited to spend a few days with VillaMore, whose curated collection of luxury cave villas in Oia makes you disregard a world outside the island. Having stayed in a cave house in the quieter village of Imerovigli just a year before, I was intrigued to see how staying in the heart of it all would measure up. Just steps away from the cinematic chaos of Oia Castle, but blissfully out of view, I found my retreat.

The villa was an architectural love affair. There was a minimalist kitchenette, perfect for assembling a mezze-and-wine spread for the terrace, and a soft and unexpectedly large bohemian lounge space that made it dangerously easy to lose hours to absolutely nothing. But the real scene-stealer? The infinity jacuzzi. A plunge into panoramic theatre. From there, I sat in the bubbles, tracing the cliff-line past Imerovigli, past Fira, all the way to Akrotiri at the southern tip, until the light faded at dusk across the caldera like a slow-burn symphony.

Though many staircases down to the villas are marked as private, happy snappers still make their way down to get their uninterrupted pictures. In this case, my concerns about being disturbed by holidaymakers were ousted by the perfect location of this villa. Tourists roamed above, selfie sticks on high alert, but the villa sat just far enough below to be hidden from the circus. I could float, undisturbed, the entire curvature of Santorini’s crescent stretched out like a Greek goddess before me.

We chose to pop the bottle of wine kindly left for us by our hosts, and watch the island turn orange in the sunset light of, over a game of UNO of course. Why battle the hoards of sun-worshippers jostling for elbow space at Oia Castle when the best part of the show is taking place in your own front yard?

Morning brought its own rituals. We woke early on most days and took breakfast at Meteor, a café-meets-time-capsule perched just above the villa. Jazz music spilled softly from the open doors onto the view, so absurdly dream-like I kept forgetting to eat. When I could no longer pretend that I had any of my freshly squeezed orange juice to sip on, I ventured out into Oia. Yes, every dress-flipping Instagrammer was out in force. But even here, Santorini offers surprises. Turn a corner, descend a staircase, and suddenly it’s silent.

SANTORINI, With All Its Contradictions

Oia’s luxury cave houses in aren’t just a trendy place to sleep. They are, quite literally, the essence of the island. Once symbols of scarcity, now redesigned sanctuaries, an architectural plot twist befitting of a Greek island. I leave a piece of myself in Santorini each time, between the caldera and the sky, on the silent staircases of Oia at dawn, and somewhere inside a simmering jacuzzi under a sky gone lavender. If you’re curious to meet other sides of the island, you’ll find more in my full Santorini travel guide.