12 Best Hotels in Santorini (Thira), The Cyclades

On one of the island's highest points, these six sumptuous villas offer a 21st-century interpretation of the classic Greek-island hideaway, built in a traditional style with careful respect for Cycladic architecture, with smooth white walls standing out brilliantly against the surrounding dark volcanic stone and the deep blues of the Aegean Sea. The villas are simple in design but entirely luxurious, with a fireplace, private veranda, and modern amenities, and a plunge pool in two. In the common area, a breathtaking infinity pool that has graced the cover of many a travel magazine sits on the edge of the caldera, offering unforgettable sunset views.

Stunning decor and earthy Cycladic charm blend into what is truly Santorini splendor; think sparkling white cubes with volcanic stone trimmings surrounding an 18th-century mansion. Interiors are picturesquely dotted with domes, skylights, and interior windows, and the decor is a fantasia of Chippendale armchairs, ancient amphorae, Byzantine icons, Corfiot mariner's chests, Picasso ceramics, and gilt-framed engravings; the glowing color schemes were cooked up by legendary British designer David Hicks. The showpiece is the "House of the Winds," where the grand, double-height, cathedral-roofed living room shimmers with elegant antiques and robin's-egg-blue walls. The elegant communal terrace overlooks the caldera, but many choose to enjoy dinner on their own terraces. A splendid cliff edge villa has been added to the collection.

A former convent from the 18th century has been converted into the most comfortable and discreetly luxurious, as well as the most poetic and serenely quiet, place to stay in Fira. This is an aristocratic haven of heavenly fabrics, marble floors, antique furniture, 19th-century engravings, and sublime terraces and balconies overlooking the caldera. There is impeccable 24-hour service, fresh flowers, and a gourmet Mediterranean restaurant that will serve you on your private terrace or in a deep, charmingly decorated cave house.

Santorini's traditional Cycladic style is married with contemporary design through the use of natural materials and textures in this relative newcomer. Rooms are simple, spacious and luxurious and all come with their own pool but it is the location that is spectacular; Armenaki sits between Ia's two blue domed churches and has awe inspiring views. Meticulous attention to detail and flawless service elevate this establishment above its neighbors.

This intimate sanctuary is a special place to stay, with terraced, vaulted-ceilinged cave houses that are sophisticated and full of character—the rooms are filled with beautiful multicolor tiles and plush beds tucked into alcoves, with private Jacuzzis and small pools in some. Romance fills the air at dinner time in the Five Senses restaurant with panoramic views at the top of the property where the food, setting and service combine for memorable meals. 

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 23 suites and villas 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 Thirasia, only accessible by helicopter or boat. Like the lair of a James Bond baddie, it is utterly stunning.

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.

Though there's no view of the caldera, a slant of sea view is effulgently wonderful—add in the large freshwater pool, excellent service, and location in central Fira, and the sum total makes these large, bright rooms a very popular option. Accommodation overlooks the soothing expanse of the sea from terraces and balconies. Santorinian-influenced gourmet dishes are served in the attractive dining room, and the spa is considered one of the best on the island.

The Canaves Oia brand seems to open a new property every season, but this is the original development and still one of the best—a recent refurbishment has resulted in a collection of beautifully furnished suites, all done in crisp whites and handsome fabrics, 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.  For the ultimate romantic meal book the Panorama Terrace—only one table and one seating per night.

A perch at the far eastern end of Ia provides inspiring 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 byword with most of the rooms having their own whirlpools. The center of Ia is a 15-minute walk away, keeping the crowds at a distance.

Sumptuously furnished, this immaculate white cliff-side complex layered on terraces offers ultimate luxury and sleek modern design, with bright 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 contemporary and private; all have terraces that overlook the caldera and are luxuriously appointed. Toast the sunset with lobster and Champagne from the Fleur de Miraval Bar, or better still, retreat to Botrinis for exquisitely plated Greek dishes.

This romantically designed, adults-only getaway is seemingly in the middle of nowhere—a quiet stretch of valley fronted by farmland and with a distant view of the sea—but that is part of its secluded charm. Moreover, it is still within walking distance of the beach scene at Perivolos, one of Santorini’s most-loved black-sand resort beaches. With just 11 suites service is personal, a sparkling pool relaxes, all suites have a private Jacuzzi, and the chic whitewashed charm throughout make Orabel an immaculate luxury boutique haven.