It’s hard to believe that this iconic property once consisted of just two 17th-century “caves” that had been used to store wine when it launched in 1985. Today, the family-owned hotel has 17 rooms spread out over five floors, all of them with terraces or balconies and jaw-dropping views of the caldera and brilliant blue Aegean. The rooms were completely refurbished in 2015—followed by the public areas and infinity pool in 2017—favoring clean, contemporary lines, white-washed walls, and luxury that envelops you without distracting from the stunning scenery; several rooms feature heated plunge pools, while one has a free-form “river pool” that runs through it. A poolside bar serves lunch and snacks, but you shouldn’t miss dinner at sister property Canavas Oia Suites, just a short walk away. For a truly unforgettable experience, you can even charter the hotel’s yacht for a sunset tour.

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