When I was 13, my parents took me on my first overseas trip to the Greek Islands. I had never imagined such a color could exist as the piercing sapphire blue of the almost indistinguishable Aegean Sea and sky. My favorite photo was from Santorini, the croissant-shaped, southernmost island in the Cyclades. I was riding a mule up the precipitous incline from the port to the town of Oia, wearing a blue blazer and, hewing closely to 1974 fashion, clogs. My mother sat behind me atop another beast with a smile that said, “Here we go!”
Photography provided by Canaves Ena
The photo is long gone, but the memories of Santorini remain: widows clad in black, fishermen with rugged faces and undulating white houses built into the cliffside. I remember the caldera — the water-filled crater formed 3,600 years ago by a volcanic eruption and a bona fide geological masterpiece. What was most indelible was the remoteness of the place, and the dusty ribbons of empty streets that wound through town.
That changed in the early 1980s, in part, perhaps, because of a somewhat forgotten movie, Summer Lovers. The film was about a young couple’s sexual liberation in Santorini, and the location was almost more significant than the story. Soon after arriving in Oia (from Connecticut), a boyish Peter Gallagher turns to his girlfriend, played by willowy Daryl Hannah, and says, “I can’t tell you how this place turns me on.” Travelers, including most of my graduating college class, began flocking to Santorini, seeking that decadent mystique.
Around that time, the Chaidemenos family, who were native to Santorini but living in Athens, decided to transform the caves that had been in the family for generations — where they stored their wine, chickens and mules — into a hotel. “It was a very progressive idea at the time, and of course, everyone thought they were crazy,” says their son Markos, 36, managing director of the family’s Canaves Collection. Their five properties around Santorini are wildly chic interpretations of the sun-kissed architectural vernacular that, along with its powerful landscape and prime location in the heart of the Aegean, helped put Santorini on the map 40 years ago.
When I recently returned, I was eager to revisit the secluded outpost I remembered as a teenager. I also wanted to experience the Greek island that, since then, has become a darling among high-end travelers who love their sensuous playgrounds in the sun served up with local flavor, refined style and a chilled glass of Assyrtiko wine.
Photography provided by Canaves Ena
After four decades, the Chaidemenos’ original property was reimagined, reopening in 2024 as Canaves Ena, a boutique hotel that, despite its central location in Oia, feels like a private, exclusive villa. Each room has a zillion-dollar view of the caldera and Santorini’s fabled sunsets and is furnished—minimally and gorgeously — with coffee tables fashioned from Greek marble and ceramic vessels crafted by local artist Andreas Makaris. I visited his atelier and he guided me as I spun a bowl, one of many experiences that filled my dreamy days.
I stayed in the family’s Canaves Epitome, which opened in 2018, and where I sensed something increasingly rare in the luxury hotel space. The glamour here was not the white-hot pretentious kind, but the warm and earthy version: in the spare but exquisite room and the understated yet flawless service. “True luxury is also about plants, gardens, space and total privacy,” said Markos. “That’s why we created this sanctuary.”
Photography provided by Canaves Ena
We were chatting over an al-fresco breakfast. Birds trilled in 700-year-old olive trees that the family shipped to Santorini, where the volcanic earth allows little to flourish besides cherry tomatoes and grapes. It’s hard to decide what was more pleasing — the scent of jasmine drifting around our table or my fragrant bowl of kagianas, a sublime concoction of scrambled eggs, feta cheese, tomatoes and local sausage.
We discussed Santorini’s reputation for overcrowding, which may have been, in recent years, a deterrent (although it is Mykonos that regularly makes news for price-gouging tourists). In fact, says Markos, the island, especially Oia, is highly resistant to overdevelopment due mainly to legislation made when his father served as mayor, including a law forbidding the construction of any new establishment without another one being closed. “People said, ‘You’re killing the destination!’ But what he was really doing was saving it.”
Markos’ current mission, he said, is to preserve and promote the Santorini he knew growing up, spending every summer and holiday there. “This will always be a destination because of the natural beauty and the energy,” he said. “But it’s up to us to offer not just a hotel but a whole experience that’s different and authentic to this island.”
Photography provided by Canaves Ena
The streets in Oia were busy but not congested. Ambling through town, showered in sunshine, I ordered tender pork souvlaki wrapped in a pita that I ate on a whitewashed step overlooking the sea. The hotel arranged for a catamaran to sail around the caldera to the hot springs, where I had a soothing swim. On deck, I showered off the strong residue of sulfur. That and the panorama of black and white lava cliffs reminded me that this is still an active underwater volcano.
One afternoon, I sojourned to the island’s premier winemaker, Sigalas. It was quiet there, almost contemplative. The head of hospitality, Labrini Kouvatsi, led me through the grapevines, which are gathered into round baskets fashioned from older vines to protect them from dryness and the salt wind. The soil was a remarkable red, black and white volcanic ash. “There is not a lot of production, but the quality is outstanding,” she told me as I sipped an assortment of citrusy whites and peppery reds.
Photography provided by Canaves Ena
I descended past dramatic escarpments from the hotel to the port of Ammoudi and the hotel’s taverna, Armeni. There, I feasted on grilled prawns, tomatoes and feta and red snapper that was swimming that morning. I saw mules on the hillside and recognized it as the place I had been with my parents years ago. I smiled at the memory of my absurd footwear and my mother laughing herself to tears.
I sensed that Santorini — the perfume in the wind and my elegantly minimal room with a private pool, where I watched the sun set over the Aegean — might occupy my daydreams in icy winter. I ate decadently and slept deeply. My time in Oia was escapism with a twist. I didn’t simply laze on a beach. I engaged with the village, the sea and my past, and fell hard for the rugged landscape. I will not wait another fifty years to return.
