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Your Tuscany: Holiday Itineraries in the Heart of Chianti Wine Country

Whether you choose to rent a villa or a farmhouse in Chianti or in another enchanting corner of Tuscany, either way you’ll be just a short distance from some of the choicest vineyards, breathtaking vistas and charming villages in all of Italy. Drive leisurely along the Chiantigiana, the legendary road that winds through the rolling hills of the Chianti region, and follow in the footsteps of Machiavelli, Michelangelo and the Etruscans and Romans that preceded them. Steeped in colorful history and even more colorful cuisine, the beauty of the Chianti region beckons during all four seasons.

  • Castellina in Chianti

  • The tiny village of Castellina dates back to ancient Etruscan civilization. It was an important stop on the road that connected the ports of the Adriatic to the powerful cities of Volterra, Chiusi and Fiesole, located in the hills above modern-day Florence. Castellina has uncovered a wealth of archaeological treasures, including the epic 53-meter burial vault of Mt.Calvario, located outside of the city walls along the road to Florence. Bronze weapons, ornaments, Corinthian vases and other finds are on display in the foyer of Rocca Comunale, the current-day city hall which was once a medieval castle. The 16th-century church of San Salvatore was rebuilt after extensive damages during World War II and contains a beautiful fresco of the Madonna attributed to Bicci di Lorenzo (1373-1452) and the relics of its patron saint, San Fausto. The historical Palazzo Ugolini and Palazzo Biancardi are both located in the historical center, the latter bearing the Medici coat of arms, having hosted Pope Leo X, the son of Lorenzo il Magnifico, in 1513.

  • Panzano in Chianti

  • Panzano is home to the shop of Dario Cecchini, the “poet/butcher” who brought the village into the Slow Food spotlight when he organized a funeral for the bistecca alla fiorentina in 2000 during the height of the bans on European beef. The bistecca has since returned in full force, but this charming town has more to offer than just meat! The village takes its name from the Romans, but archeological evidence points farther back to the Etruscans. The town castle marks the halfway point between Florence and Siena; Panzano has been divided between the two feuding cities for many centuries. The castle’s courtyard and surroundings are open to visitors. The beautiful church of Santa Maria Assunta beside the castle contains a stunning Ghirlandaio fresco. Visit Panzano on a Sunday to shop the weekly morning market, where you can buy everything from produce to ceramics to clothing. The third weekend in September brings the “Vino al Vino” Festival in the main piazza of Panzano, celebrating the excellent wine and food of the area with music and festivities.

  • Greve in Chianti

  • The most visited of the Chianti hamlets, Greve in Chianti has hosted British Prime Minister Tony Blair, lending it the nickname Chiantishire. This charming town became the epicenter of the Greve valley after the unification of Italy in 1862, a considerable accomplishment considering that the town was burned to the ground by the Duke of Lucca in 1325! The church of Santa Croce houses a collection of paintings by the school of Fra Angelico and a statue of explorer Giovanni da Verrazzano presides over the main piazza. Greve in Chianti hosts the largest of the wine festivals, or sagre, each September, and a weekly market every Saturday morning livens the town square and brings out the local colors. The tourist information office with maps detailing the myriad of local wineries is located on the Chiantigiana road right in Greve, as is a large consortium center, where you can sample hundreds of different wines all under one roof.

  • Chianti Classico and the Gallo Nero Label

  • A consortium for the protection and regulation of the Chianti Classico wine was founded in 1924, adopting the noble black rooster (gallo nero) as its symbol. This symbol was used by the centuries-old league (Lega del Chianti) and the town council of Castellina.
    The Chianti region was granted D.O.C. status in 1967, meaning that its product was of a Controlled Origin, and in 1974 it was further awarded D.O.C.G. – controlled and guaranteed quality. The precise areas of Chianti Classico production are Radda, Castellina, Gaiole and several neighboring towns. Chianti Classico wine is made up of a very specific quantity and quality of Sangiovese, white Trebbiano, Malvasia and Canaiolo grapes.

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