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This dramatic, volcanic island makes a fine base of operations, as long as nightlife is not what you're after. Drink in the magnificent caldera (also the harbor), take the cable car to the capital, Fira, and spend time in elegant Oia, the gentrified village of 19th-century villas and restored troglodytic peasant houses. Note the sand here is not white but black.
The single most famous Greek island is having another moment, and it's a good choice if you like to be where it's at. With its windmills, Little Venice and Alefkandra (the artists' quarter), the main town, Mykonos, is beautiful and unusual. It's less of a gay mecca than it once was (the clothing-optional end of Super Paradise beach is another matter). Even here, seclusion can still be found in other parts of the island.
Easily accessible from Mykonos, the sacred birthplace of Artemis and Apollo, with its world-famous archeological sites, is memorably atmospheric—though less so in the boiling-hot, crowded afternoons. Try to catch the first ferry. Keep in mind that you can't stay on the island.
Less frequented by international style-seekers and Americans, though quite popular with Europeans, the third-largest island in the Cyclades has a lot going for it: great, white beaches, scores of good tavernas (cafés) and pretty fishing villages. There are also frenetic towns, more or less ruined by tourism: the two ports Parikia and Naoussa among them.
Virtually unknown to Americans, this compact island with 365 churches is one of the prettiest in the Cyclades. The distinct dearth of top-class accommodations has kept it off the map, but between the lively port Kamares, the inland capital Apollonia and sleepy, medieval Kastro, there's a lot to like. And Sifniot chefs are said to be the best in Greece.
The chief Ionian island seems more Italian than Greek—it's near the toe of Italy and was under Venetian rule for four centuries. Tragically, much evidence of that period was razed by the massive earthquake of 1953, but the ocher and pink houses still differ from the white-and-blue Aegean norm, and the Italianate capital is downright elegant. There are also big beaches and party towns for mass tourism, plus quiet, upscale villages. Hotels aren't great; the best way to stay here is to rent a villa.
Like Corfu, the chief island of the Dodecanese chain differs greatly from the Aegean standard, though here it's not Italy but neighboring Turkey that has exerted its influence—the Ottoman rule lasted 300 years. Rhodes Old Town is Europe's biggest inhabited medieval town, worth seeing for its three-mile ramparts alone.
The biggest Greek island has quite distinct attributes due to its size, its mountainous topography and the fact that it's the birthplace of the Minoan culture. Archeology buffs are in heaven here, with the magnificent Heraklion Archaeological Museum (Xanthoudidiou St.; 302810-226092) and the Minoan Palace of Knossos being the greatest of sights.