The Kapetanospito (meaning sea captain's house in Greek), built by the ship-owning Sigouras Sarris family, is as old as the Greek constitution and is one of a very few historic-preservation houses in Oia. By village standards, this is a very grand place, with its double-terraced front with false pillars of volcanic red rock, courtyard, and wide-plank floors; yet it's also typically Santorinian, with high vaulted ceilings and an interior partially carved into the cliffs. The hotel is split into two villas and three suites; although it's possible to rent the whole place to yourself. All the rooms have canopy beds and are crammed with antiques and local artwork. For those who prefer staying on the grid, this place is ideal: There's satellite TV, DVD and CD players, Wi-Fi, voice mail, AC—everything, that is, except a pool. But there are Jacuzzis in all three suites, and the village beach is only a ten-minute walk away. There's also an epic breakfast and a ten-percent discount at two of the best local restaurants, Ambrosia and Ambrosia & Nectar (formerly Oia's Café-Restaurant), because the hotel owners own them, too. You can also opt for über–room service on your suite's rooftop terrace. For those interested in some pampering, there's also an on-site Caldera Massage Studio.

Closed December to February.

You don't need a secret handshake to get in, but in an effort to discourage gawkers on what is, after all, Oia's main pedestrian thoroughfare, there's no signage on the front of the Andronis. What looks from the street like a restored sea-captain's mansion now housing a private club is in fact a 13-suite hotel that combines all the best elements of a Santorini cliffside stay. Its creative cave room design includes such elements as private plunge pools, beds raised on stone platforms, and Aegean views. An all-organic restaurant will serve your Greek salads poolside, where every day at sunset there's a private wine tasting. True sybarites will enjoy the massages (given in a cave, of course), and the strawberries and champagne that are part of a wholesome Andronis balcony breakfast.

More reliable ferry connections, featuring a twice-daily run of the high-speed hydrofoil from the mainland port of Piraeus, are transforming Folegandros into a destination for travelers seeking an unspoiled outpost. Surrounded by a midnight-blue sea and nestled amid arid mountains blanketed with wild thyme, Anemi's 44 accommodations are in two-story bungalows linked by stone pathways that wind through aromatic gardens. The heart of the hotel is the minimalist lobby, restaurant, and glamorous infinity pool. The suites, with private verandas and kitchenettes, have contemporary furnishings and vibrant photography that contrast with hand-hewn beams and oversized wood doors. The complimentary breakfast includes a blitz of fresh pastries, egg dishes, and yogurt with local honey and can sustain you into late afternoon. Nightfall presents the option to dine poolside, although the staff will gladly drive you the two miles to the island's main village of Chora. One of the Cyclades's oldest medieval towns, picturesque Chora is cordoned off to car and moped traffic and offers plenty of inexpensive dining under a lantern-lit canopy of trees.

Built in 1993, the family-run Anemomilos was one of the first boutique hotels in the Cyclades to appear somewhere other than Santorini or Mykonos, and it has continued to please. For one thing, its setting is spectacular: From atop a sea cliff, the 16 studios (each with an open-plan sleeping-living-kitchenette arrangement) all boast views only slightly less panoramic than those from the caldera of Santorini. (For the best views, opt for a blue-line apartment, or just hang out at the pool.) Additionally, the management is unusually progressive: They have long offered, for instance, a room designed with disabled guests in mind—something about as common in Greece as a nonsmoking section in a restaurant. The room decor is simple, pretty much the same traditional white with blue trim as the exterior, but it goes well with the simplicity of the island, which is just hard enough to get to that you won't be bothered much by the types of people who, if they do travel at all, should really spend their entire time on Santorini.

Closed October through March.

A Bellini thrust into your hand on arrival sets the tone at this adorable 17-room hotel, a ten-minute walk from Mykonos Town and close to the beach. It looks similar to the standard whitewashed cube with blue shutters, but inside it becomes clear someone cares. That someone is young owner Kriton Harakopoulos, who has decorated the place with drapes, planters, rugs, and other accents that add a homey chic. He also offers a cornucopian breakfast of croissants, pancakes, eggs, chocolate muffins, homemade bread, yogurt, and honey (served until early afternoon). AC, TV, room service (till nearly midnight), Molton Brown toiletries, and a floodlit freshwater pool with an adjacent bar complete the picture.

Closed October to April.

You can still top out at over a grand for one of the new private-pool suites at this Santorini cliff-hanger, which is split into 16 traditional-style apartments and 12 eclectic suites. But price being a relative thing, it just may be the most undervalued place to stay on the island. The decor is art-hotel chic. (The red bathroom in one of the Jacuzzi suites registers at just below over-the-top.) The caldera views, from poolside or private patios, are better even than those from Oia. Manager George Karayiannis is always so cheerfully ready to deal with any request (You need to borrow a laptop for your stay? No problem, no charge), you almost wonder if he is really Greek. For some, the only drawback here are the steps, which are numerous even by Santorini standards. A few trips up and down them should add greatly to even the most fit guest's appreciation of the hotel's new restaurant.

Closed November through March.

Checking into the Belvedere for the first time, you'll feel like you died and went to somebody's first wedding. Everything's white, right down to the shoes on the staff. That fact—plus the poolside pose-and-party scene, the slick cocktail lounge, the Nobu outpost, the clientele of jet-setters and A-gays stopping off between Bodrum and the Hamptons—makes this a slice of South Beach in Mykonos. If you're here to take in the nightlife and rub shoulders with the fashion flock, the Belvedere is the best place to stay. That's not the only reason to check in, though: Service is above the island norm (Pablo will take excellent care of you at the pool), and rooms, though moderately sized and not as elegant as the public spaces, come with niceties that are rare in other Mykonos properties (flat-screen TVs, cordless phones and hotel-wide Wi-Fi, bath products from Korres, and firm mattresses. The least-expensive rooms look out onto shrubbery; spring for a better view, since the hotel is located at the top of town, a superb position for sunsets. That also means you're a few minutes' walk (assuming you don't get lost among the alleyways) to everything in town. And when you get sick of tzatziki, there's sushi at hand, too.

Closed November through mid-April.

When an architect is given free license by a hotel owner to create a new look for a property—which usually happens only if the architect is the owner—the result is sometimes successful. And so it seems to be with the Hotel Cavo Tagoo, which was recently revamped by its new owner, award-winning Greek architect and builder Paris Liakos. To the 69 existing rooms and suites, all updated to exude a minimalist Cyclades chic, 11 suites were added in summer 2008. The new suites have private pools and are adorned with art objects that are hard to ignore, such as a full-size, all-white sculpture of a donkey. The most interesting architectural element, however, is the way the natural surroundings are worked into the design—for example, a slice of cliff facade on display behind a glass wall in the lobby. The new, Mediterranean menu by chef Nikos Skliras seems to have passed muster, too, with the crowd settling in for the evening at the poolside tables (recently including designers Giorgio Armani and Jean Paul Gaultier and supermodel Karolina Kurkova). Two shortcomings exist here: The hotel is tantalizingly close to walking distance from Mykonos Town, but the walk requires guests to negotiate a narrow cliff-side road whose risk factor for pedestrians ranges from hazardous to deadly. And while the day-long construction noise just across the road will eventually result in a new yacht marina (in 2010), it is for now not the most desirable background sound for an Aegean idyll.

Closed October 22 through May 14.

Rocky cliffs are home to white cubist cottages perched more than 300 feet above Santorini's water-filled caldera. The shades of the water below are reproduced in the two infinity pools and the light-blue interior walls—"the visual effect is quite stunning." At the restaurant, tackle Mediterranean cuisine on a candlelit veranda, or sample cocktails poolside at Kirini.

(27 rooms)

Similar in design-driven style and ambience to its better-known sister, the Katikies, which is a few steps along the caldera, this 19-suite hotel (formerly the Katikies Suites) features a small outdoor pool (claim your lounge chair early) as well as an indoor spa pool, whirlpool bath, and steam room. In addition to poolside dining, there's the four-table White Cave restaurant, which, when the candlelight is casting shadows on the walls, feels so romantically retro that you almost expect the waiter to offer a special of rack of brontosaurus, prepared with fresh sage and a hint of rosemary. This is another hotel with an accommodating staff, who guests can reach no matter where they are on the island, via the cell phone they are given at check-in.

Closed November through March.

This neoclassical mansion, atop Imerovigli village overlooking the caldera, has nine rooms (four can be combined and rented as a private villa). The rooms come in shades of ocher, raspberry or apple, and are packed with antiques and heraldic flourishes. In addition to offering AC and standard in-room electronics (except Internet), the full-service hotel has a modern spa-hammam. Staff can charter you a yacht, chauffeur you a car, pilot you a helicopter, or organize you a wedding, which is something it frequently does. The restaurant, La Maltese Gourmet, is exclusive and good, and there are daily wine tastings for guests.

Closed October to March.

During the 2005 season, Mykonos rose another notch on the groove-o-meter thanks to the opening of this 52-room retro pad right next door to the famous windmills and "Little Venice." The Theoxenia evokes the 1960s—when Mykonos was a key jet-set party town and Ari and Jackie were regular visitors—thanks to an original structure by Greece's premier architect of that decade, Aris Kostantinidis. Inside there are walls of rough stone, turquoise and tangerine paintwork, Hessian drapes and op art prints, as well as space-age tables, and bucket chairs. Despite the lack of beach (there's a big pool) and dearth of views from the cheaper rooms, it's still a thoroughly hip place to stay.

Opened in May 2007, the 18-suite Mystique is a sister to the Vedema, one of Santorini's best hotels—except it overcomes the Vedema's major shortcoming: an inland location that leaves it with no view from the caldera. Mystique's view, back toward the main town of Fira, which itself drips like white paint over the cliff's edge, is outstanding, as is its exterior, featuring traditional Cycladic architecture. (The room decor, however, is so simple, it tends toward the bland.) The pool is small even by Santorini standards, and there are few other places in Oia with as many steps. But make your way down and you'll be rewarded by the additional privacy those steps ensure, and by a modern-Med restaurant with a wine cellar, dug into the cliff wall, that boasts one of the most extensive selections on the island.

Closed mid-November through mid-May.

Once they check in, guests say they don't want to leave this 21-room oasis within (somewhat distant) sight of the sea. Although that may have something to do with the ten-minute walk back into Mykonos Town, along the busy main road that runs by the front of the hotel. But it's also true that the free-form pool, with its hammock and lounge chairs within easy range of the poolside bar, makes the property a particularly pleasant sanctuary at which to wile away an afternoon. All the rooms were renovated for the 2007 season and now feature requisite boutique-style, minimalist, white-on-white decor. The variance in room sizes makes it worth ponying up for a more expensive category, such as an executive suite complete with whirlpool bath, full kitchen, and balcony.

Closed October through March.

In the 1970s, owner Costis Psychas and his late mother had the prescience to buy a group of 300-year-old cliff-side cave dwellings, formerly owned by local fishermen. This was a time when nobody was coming to Santorini, let alone Oia, because it was still all about Mykonos. Having lovingly restored the houses one by one, Psychas now has the 20 most desirable rooms and suites in the Cyclades—each of them curvaceous and white, with fascinating nooks and crannies, local antiques, handwoven fabrics, wood-accented domed bathrooms, and divine private stone terraces. It's all so spare and tasteful, you probably couldn't find a travel magazine that hasn't featured Perivolas. Outside, an infinity pool melts over the cliffs, and everywhere you look there are wild figs, vineyards, geraniums, and bougainvillea. There are no TVs, but there is AC; there are no minibars, but there are kitchenettes with wine, water, and coffee. Breakfasts are bountiful, home-baked, and available late. Service is perfectly discreet and efficient. Be warned, you need to book several months in advance. No children under 16 allowed.

Closed November to March.

You have to be impressed with this newest creation of the upstart but upscale Grace Hotels Group (they are already on Mykonos and have plans for Kea and beyond), if for no other reason than as a latecomer, it still managed to bag one of Santorini's best locations. Perched on the side of the caldera in Imerovigli, it offers the kind of views that are most helpful in defining romance. The rooms and suites—some with plunge pools, the ones farther down the caldera tending to be more private—are all well conceived, although the white-on-white decor has become so pervasive as to seem upscale-ordinary. With only nine rooms and suites to look after, the young but enthusiastic staff has so far shown they can do pampering well. Plans for the 2009–2010 season, however, are to increase the number of rooms to 20—and then we'll see if the waiters at the in-house restaurant can remember everyone's name.

Closed November through early April.

Traditional architecture and personal service are the keynotes of this 50-room lodging. Big, sunny rooms with beamed ceilings or whitewashed arches have floral or plaid curtains, sparse but comfortable upholstered furniture, satellite TV, minibar, and AC. An infinity-edged swimming pool overlooks the rooftops and is bordered by a bar, and there's also a Jacuzzi and a small gym. The restaurant is worth a visit even if you're not staying here; it's in part of a renovated patrician house and has an airy trad charm without being hokey in the least. It's also a nice spot for breakfast. Rohari is just above town, next to the Belvedere, five minutes from the port and Megali Ammos beach.

About as far as you can get from whitewashed, Cycladian monkish cells, these five suites and a villa are the work of art and antiquities collector Dimitris Tsitouras—whom you can credit with putting what he calls "the Pompeii of Greece" on the upscale travel map in the first place. Collaborating with British interior designer David Hicks, Tsitouras has filled the suites, all featuring typical Santorini vaulted cathedral ceilings, with choice pieces from his collections. Hence you'll find Venetian mirrors and Murano-glass chandeliers, Biedermeier chairs, Russian icons, 16th-century nautical maps, and even a rare Picasso ceramic relief. The result is incredible. An early adopter was Gianni Versace, who rented the whole place for a month—you can extrapolate from there to get a visual. Whether you pick the House of the Sea, House of the Winds, House of Portraits, House of Porcelain, or House of Nureyev suites (each named after the principal theme of the collection within) or the newest addition, the three-bedroom Tsitouras Villa (the family's own house, with the best antiques of all), you'll have plenty of luxuries: CD and DVD players, satellite TV, a free bar, and silver-service breakfast. The friendly staff is headed by Tsitouras's daughter Eleni.

Closed November to January.