Messina, Sicily, Italy
The blue Ionian Sea laps at Taormina's celebrity-studded shores. The beautiful people and their escorts arrive by the yachtful to wine, dine, and otherwise occupy idle time in this rich man's resort nestled along the cliffs. Long before the sailing set raised the per capita income, the Greeks left their mark with an impressive amphitheater (the Teatro Greco) whose origins date from the third century B.C. The Romans did some redecorating in the intervening centuries to accommodate battling gladiators and their animals, but the dramatic view of the Sicilian coast and Mount Etna's glorious snow-capped peak remains.