The summer of 2011 was not a good one for tourism in the Cyclades. Consequently, many hotels did not raise their prices. The minute that things improve, prices will go up, so be especially sure to double-check prices when you make your trip.
Santorini is stuffed to the gills with visitors in July and August; try to make a reservation with a deposit at least 2 months in advance; we consistently hear travelers' tales of miserable nights spent sitting up all night on those stiff wooden Greek cafe chairs. We also hear tales of hotels more than doubling the price on remaining rooms. Except in July and August, don't accept lodging offered at the port unless you're exhausted and don't care how meager the room is and how remote your lodging is from what you want to see when you wake up the next morning. Still, in July and August, be grateful for whatever you get if you show up without a reservation.
The island's cave houses have inspired many hotel designers. Barrel-vaulted ceilings and perhaps even a bathroom carved into the rock distinguish a typical cave house. Built for earthquake resistance and economy, some of the spaces may at first strike you as cramped; you'll soon see them as part of the island's special charm. The best of them are designed with high ceilings, airy rooms, and good cross-ventilation, because they are carved into the cliff face, they remain relatively cool throughout the summer.
Many apartments and villas have efficiency kitchens, but the facilities may be minimal. If you plan to do much cooking, check first to see what's in the drawers and cupboards, or you may find yourself frustrated if you try to prepare anything more elaborate than a cup of coffee.
For higher-end hotels, have a look at www.santoriniluxuryhotels.com; keep in mind that it is usual for hotels to pay a fee to be listed in these services.
In addition to the choices listed, we get good reports on the long-popular and usually quiet 25-room Hotel Atlantis (www.atlantishotel.gr; tel. 22860/22-232), where guests can spend the sunset hours with a bottle of wine on the balcony overlooking the caldera. The tony eight-unit Enigma Apartments (www.enigmahotel.com) appeared in Odyssey magazine's "Best Hotels of 2009." Furnishings are elegantly simple; the views of the caldera and sunsets are spectacular. The Enigma is the sister hotel of another longtime entry in Odyssey's best hotels list: ASTRA Suites, in Imerovigli. A perfect Santorini vacation would be divided between these two hotels: Enigma, in the island capital, and ASTRA, in one of Santorini's most perfect villages. For a (much) more modest place, consider Loizos Apartments (www.loizos.gr); there's no caldera view, but it's a quiet Fira location and helpful owners.
Note: Due to the noise throughout Fira, you may want to consider staying in one of the villages out on the island, unless you stay in one of the quieter hotels we suggest.
This quieter and often less expensive neighborhood is just a 10-minute walk from Fira. The views of the caldera are just as good, if not better.
The next village north along the caldera rim is named because it is the first place on the island from which you can see the rising sun. The name translates as "day vigil." By virtue of its height, Imerovigli also has the best views on this part of the caldera.
While everyone else is jostling for a place to see the sunset at Oia, head to Imerovigli and take the path over to the promontory of Skaros, with the picturesque remains of its medieval kastro. Amazingly, this deserted and isolated spot was the island's medieval capital. It's a blissful place to watch the sunset.
Imerovigli and Oia have a considerable number of attractive and comfortable places to stay. In addition to the places listed, you might want to consider La Maltese (www.lamaltese.com; tel. 22860/24-701), a member of Relais & Châteaux, in a restored sea captain's neoclassical mansion now fitted with indoor and outdoor pools, hamam and sauna, restaurant and piano bar, and of course, that caldera view.
About 2km (1 mile) southeast of Fira, this small village knows the tourist ropes, and has many new hotels and rooms to let. Buses stop at the top of Karterados's main street on their ways to Kamari, Perissa, and Akrotiri. Nevertheless, the location is somewhat inconvenient, not especially close to Fira or to the beach. Karterados beach is a 3km (2-mile) walk from the center of town. Get to Monolithos, a longer beach, by continuing south along the water's edge an additional 1km (1/2 mile).
Oia's chic shops (check out the Art Gallery and Art Gallery Oia on Oia's meandering main drag), boutique hotels, and gorgeous sunsets make it an increasingly popular place to stay or to visit -- especially for travelers who find Fira too frenetic.
If you're running low on reading material by the time you get to Santorini, head to Atlantis Books (tel. 22860/72-346; www.atlantisbooks.org) in Oia, run by a group of expat Brits and Americans as well as several Greeks. You'll find everything from guidebooks and detective novels for the beach to poetry and philosophy.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.