6 Best Hotels in Santorini (Thira), The Cyclades

The Canaves Oia brand seems intent on buying up every spare property in the town, but this is the original development and still the best—a collection of beautifully furnished suites, all done in crisp whites and handsome fabrics, meticulously maintained and enjoying uninterrupted caldera views and private pools in every room. While the sophisticated surroundings and setting in the center of Ia lend an international air, the owners and managers are a local family who ensure a very high standard of traditional island hospitality. The infinity pool with partially submerged loungers and private cabanas is great place to soak up those volcano views.

At this welcoming collection of sparkling white, arch-roofed cave houses that spill down the side of the caldera, homey suites and studios all have cozy sitting areas, well-equipped bathrooms, and a private, view-saturated terrace overlooking dark cliffs and turquoise seas. Rooms are furnished with traditional wooden pieces with bright fabrics and supremely comfortable mattresses. A romantic dining terrace serving a choice selection of well-prepared island favorites clings to the side of the cliff, a sparkling half-cave swimming pool is carved out of the rock, and a path descends toward the beach and fish tavernas at Ammoudi.

A perch at the far eastern end of Ia provides wonderful views of the village as well as the caldera, which can be enjoyed from the private terraces of the handsomely furnished cave houses that were once used as workshops to repair and store fishing nets. Nowadays, minimalist luxury is the by-word with most of the rooms having their own whirlpools. The center of Ia is a fifteen-minute walk away, keeping the crowds at a distance.

Sumptuously furnished, this immaculate white cliffside complex layered on terraces offers ultimate luxury and sleek modern design, with Warhol wall prints, stunning fabrics, and handsome furniture—chic as the surroundings are, though, the barrel-vaulted ceilings and other architectural details also lend a traditional air to the place. Suites and villas are small and private; all have terraces that overlook the caldera and are luxuriously appointed. Toast the sunset with sushi and Champagne from the Seltz Bar, or better still, retreat to Mikrasia for exquisitely plated Greek dishes.

A travel magazine favorite, Perivolas lives up to the hype and then some. That infinity pool still makes you gasp and the rest of the hotel is no slouch. The twenty houses have been converted from old wineries and stables in archetypal yposkafta (vaulted cave) fashion, with clever nooks for beds, sculpted walls, and sumptuous bathrooms; all are simply but handsomely furnished with handmade wooden pieces and weavings. Quietly glamorous and very private, you will start to fantasize about living here forever.

Even more exclusive and guaranteed to unleash your inner rockstar is the hideaway from the same owners across the water in Therasia, only accesible by helicopter or boat. Like the lair of a James Bond baddie, it is utterly stunning.