With its hilltop medieval towns and rolling landscapes, art-filled cities and vineyard-set villas, Tuscany epitomizes Italy for many travelers. After all, this is the birthplace of Italian icons like Leonardo da Vinci and poet Dante Alighieri, considered the father of the Italian language, and of signature flavors like bisteca Fiorentina and Chianti wine. Bordered on the west by the Tyrrhenian Sea, Tuscany’s position in the heart of the Italian boot is particularly apt. There’s a lot of history (including several UNESCO World Heritage Sites) to soak up here, starting from the days of the ancient Etruscans, after whom the region is named, through the era of the powerful Medici clan, makers of Popes and patrons of the Renaissance. Explore cities like Florence, Siena, Pisa, and Lucca, each filled with plenty of cultural, dining, and retail distractions, then spend some time in the countryside, taking in historic towns, legendary wineries, and nearly 250 miles of coastline.