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Chianti Classico, Tuscany’s Most Beloved (Wine) Region

With its sweet rolling hills, untamed nature, ancient castles and honey-coloured stone villages, the lovely wine region of Chianti Classico is surely one of the world’s most beloved vacation destinations. Split between the provinces of Florence and Siena, this photogenic part of Tuscany attracts both local and international tourists, who come here to enjoy the simple pleasures of life. But what’s at the root of the world’s love affair with this countryside dotted with vineyards and olive groves? Wine may provide an answer, but it’s just one of the reasons. Just a short drive from the Cradle of the Renaissance, you will find a region full of history, a landscape where each changing season brings new wonder, a myriad of picturesque towns in which to enjoy unique experiences and pamper yourself with the greatest food. In order to make things easier for you, we have compiled a list of our favourite Chianti Classico destinations, so that you can consider adding them to your travel itinerary.

1. Greve in Chianti

Considered by many as the gateway to the Chianti wine region, Greve in Chianti lies just a stone's throw away from Florence and boasts an attractive, triangular-shaped piazza that has been a marketplace since the Middle Ages. Piazza Matteotti is the ideal location for a Sunday lunch in a typical Tuscan trattoria and a fantastic place to stroll and shop before going wine tasting in one of the many local wineries. Other places of interest in Greve in Chianti include the Museo del Vino, Enoteca Falorni and Antica Macelleria Falorni – the oldest butcher shop in Italy. If you happen to be in town the first or second week of September, don't miss its worthwhile wine festival, during which a variety of wines, cheeses and other Chianti products is available for tasting.

2. Montefioralle

Situated on a hill, about 2.5 km from Greve, Montefioralle is a small, fortified village that is claimed to be the place where Amerigo Vespucci was born. Entirely surrounded by sangiovese vineyards and olive trees, Montefioralle retains its elliptical shape and is considered one of the most beautiful medieval villages in Italy. On a visit to Montefioralle, make time to watch the sun go down from the pretty Chiesa di Santo Stefano or explore one of the many family-run wineries that surround the village’s original nucleus. This little jewel of a village also has some cute little shops and a couple of good restaurants in which to taste specialties such as ribollita, pappardelle pasta strips in wild boar sauce and the famous thick-sliced T-bone steak.

3. Badia a Passignano

A 15 minutes’ drive from Montefioralle is Badia a Passignano, a cluster of towers, houses and cypresses interrupting vast mosaics of vines and olive groves. This tiny medieval hamlet is a real photographer's delight and is best known for its strikingly beautiful abbey whose construction started in the 11th century. Besides taking a tour of the abbey, visitors to the village can take unforgettable walks through the surrounding hills (a protected area since 2008) and enjoy a traditional lunch in a graceful osteria that serves typical Tuscan dishes with a twist. The osteria also has a lovely bottega, where wine lovers can taste and purchase delicious Antinori wines, marmalades and truffle specialties.

4. Panzano in Chianti

About 9 km from Montefioralle you will also find Panzano in Chianti. A hamlet of Greve, Panzano is best known for its 12th century castle that played an important role in defending the Florentine Republic during the battles between Florence and Siena. Panzano’s old village is very pretty, one of those places where you can sit back and really soak up the atmosphere from times gone by. Places of interest in and around the village include the Oratorio di Sant’Eufròsino (also mentioned by Oriana Fallaci in her book “A Hat Full of Cherries”) and Antica Macelleria Cecchini, a butcher shop & restaurant that is famous for its juicy bistecca alla fiorentina. The butcher Dario Cecchini is just hilarious and often recites Dante’s Divine Comedy to its customers.

5. Castellina in Chianti

Included in the province of Siena, the compact market town of Castellina in Chianti was established by the Etruscans and fortified by the Florentines in the 15th century in order to create a defensive outpost against the city of Siena. Castellina’s most prominent feature is definitely Via delle Volte, an astonishing tunnel-like road that offers breathtaking views over the manicured countryside. Other interesting sights in Castellina are the Museo Archeologico del Chianti Senese (housed in the imposing medieval rocca) and a couple of late Renaissance palazzi: Palazzo Ugolini-Squarcialupi and Palazzo Bianciardi. Just outside the town centre you can visit the Burial Mound of Montecalvario, a passage tomb that dates back to the 7th century BC and attests to the presence of the Etruscans in the area.

6. Radda in Chianti

Still surrounded by its ancient town walls, charming Radda in Chianti has maintained its medieval character and makes an ideal base from which to tour the classic Tuscan vineyards. Together with Greve and Castellina, this municipality of 1587 souls is one of the major wine and administrative centres of Chianti and surely one of the prettiest places to stay while visiting Chianti Senese. Radda’s main square – Piazza Francesco Ferrucci – houses the 15th century Palazzo del Podestà (the headquarters of the League of Chianti for over four centuries) and the graceful Romanesque Church of San Niccolò. Just 7.5 km out of town, you can visit the picturesque hamlet of Volpaia, where particularly delicious wines, olive oils and vinegars have been produced for centuries.

7. Gaiole in Chianti

Not far from Radda lies Gaiole in Chianti, another beautiful small town that deserves a closer look. Mainly known for L’Eroica – a vintage bicycle race that takes place on the first Sunday of October – Gaiole dates back to the Middle Ages and was an important marketplace for the castles in the immediate surroundings. While there isn’t much to see in Gaiole in Chianti, the town has great wine shops and rustic wineries perfect for sampling classic Chianti wines, Super Tuscans and dessert wines. 15-20 minutes drive from Gaiole is the magnificent Brolio Castle, the oldest winery in Italy, where the Ricasolis have made great wines since the 12th century.

Advice for wine lovers: remember that most of the best wineries are in the remote depths of Chianti Classico. It helps to have a driver who is happy with the so-called “strade bianche”, those picturesque and unforgiving roads criss-crossing the Tuscan countryside.

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