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The achingly beautiful Tuscany region of Italy is a touchstone of art, food, and culture. Made up of stunning countryside and distinguished cities, Tuscany is the perfect escape for gastronomes, cognoscenti, and fans of the Italian Renaissance. Visit the stunning Roman Catholic cathedrals and galleries of Florence and Arezzo, or make your way to Pisa to see its hallmark Leaning Tower. A bike tour through olive groves and vineyards is a popular way to literally breathe in the Tuscan atmosphere.
This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvelous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a medieval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.
Lucca's array of wonderfully intact historical sites makes it a must-see stop on any Tuscan itinerary. The medieval city walls still stand—you can hike or bike on top of them. Also visit the Duomo di San Martino and the Roman amphitheater.
Perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun,” gorgeous hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell'Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.
While crowds of tourists fill Venice, Florence and Rome, Bologna remains relatively quiet in comparison. This medieval university town is charming, historic and fun to explore… and you'll find Bologna's local cuisine is light-years away from the American deli meat bearing the city's name.