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Discover the Chianti food & wine culture

The Chianti region with its hilly countryside of incomparable beauty lies in the very heart of Tuscany. Chianti is the result of a true love of people for their countryside. The manicured vineyards that cover hill after hill are a festival for the eye. The taller hills have medieval castles built on top of them, or secluded abbeys or sumptuous villas. The best way of discover the Chianti region is a classic convertible. The laid back and inspiring roads are far away from the traffic congestion which we are used to these days. And there is no better way to enjoy the views, the sounds and the smells of this area of Tuscany.

The Chanti region stretches from Florence to Siena, and there are two main roads crossing it, the Cassia, and the Chiantigiana. We will opt for the latter as being more rural and scenic. Throughout the Middle Ages, Chianti saw the continuous fights and war between Florence and Siena to impose their control on the area, until 1555 when the Medici imposed their hegemony on all of Tuscany. This long time feud is still very well alive today, after 5 centuries. Have a chat with a Florentine or a Sienese and the rivalry will sparkle.


Our proposed itinerary starts from Florence and ends in Siena and it will take 2-4 days to complete, depending on how frequently you stop (it will end up being VERY often).

Just outside Florence the famous Charterhouse (Certosa) is the ideal starting point. This is a stunning walled Carthusian Monastery, built in 1341, which served as an inspiration to Le Corbusier. From the charterhouse we'll take the Cassia for a short stretch, leaving behind a congested motorway, and head toward Greve, following the Chiantigiana. You will be delighted by the quiet scenery surrounding you as if you were already miles away from the modern life.

Greve in Chianti is the most important village in the Chianti region and home to the largest wine fair in the area, which is held every September. At the end of the Middle Ages Greve established itself as a market place and trading centre for many of the surrounding fortified villages, castles and farms. Although Greve was destroyed in 1325 by the Duke of Lucca, the town came back to life and continued to grow during the fourteenth and fifteenth centuries. Today a walk in the piazza means a discovery of many traditional foods and wines. There are many shops to buy from, and locals mostly buy their delicacies there.

The famous explorer Giovanni da Verrazzano who discovered the bay of New York was tributed with a statue in the piazza, while the nearby Montefioralle is the hometown of Amerigo Vespucci.

We take the wheel again heading further south on the Chiantigiana towards Castellina in Chianti. The road offers breathtaking sceneries of a wilder and less cultivated countryside. Castellina in Chianti as opposed to Greve is the main center for the Cinta Senese (local pork cured meat). Take a stroll in the Piazza dominated by the castle, a sign of the eternal rivalry between Florence and Siena and then down on the high street with its a collection of elegant residential buildings: it's well worth a "passeggiata" and a stop for some salami.

A few miles ahead and we are in Radda in Chianti

Radda's history is dating back to IX century BC, but its oldest building, the castle, was in existence already in the XI century. Since the end of the XIII century, however, the territorial extension of the Council of Florence, incorporated the area of Radda into its confines. As with many of Chianti towns and villages, the best thing to do is to appreciate the elegance of the old buildings by taking a stroll along the cobbled street.

While in Radda in Chianti, a short diversion will take us to the Volpaia castle. The castle dating back to XI century was built by the aristocratic family "della Volpaia".

Back on the road we are now heading eastbound toward Gaiole in Chianti. Its origins are –no doubt- Etruscan and despite the many run downs due to the bitter fight between Florence and Siena, its old center still retains the flavour of the XVI century when the Grand Duchy of Tuscany took over the area. Another sign of the continuous fights in this area, are the unusual concentration, even in Chianti. We'll be visiting the Cacchiano Castle, built in the XIII century by the Ricasoli family; the the same family owns the Brolio Castle which was transformed into a Neo-gothic villa in the XIX century and recently restored to its former splendor; you can find the wines produced in the family estate in its fascinating wine cellars; the Monteluco Castle sits on a hilltop just a few miles from Gaiole in Chianti.

When you are in Chianti, driving is a substantial part of the enjoyment, with such a landscape surrounding you. Driving a classic car is even better as you get the feeling to have stepped back in time.

We are now moving westbound, leaving the Apennines heights behind us, toward the Via Cassia which we left at the beginning of our tour. There are a few castles on the way that are worth a stop, such as the charming Castello di Fonterutoli, before getting into Monteriggioni.

At the turn of the first millennium, Monteriggioni was already a thriving town. The castle however, wasn't built until 1213. It was built by the Republic of Siena –guess why- to defend itself from the Florentines. This castle has two large entrances, one known as 'romea' which opened onto the road to Siena and another that faced Florence. This outpost was so invulnerable to withstand well over 3 centuries of attacks. What wars didn't achieve in 350 years, a man betrayal did in one day. The town was betrayed by Captain Zeti who basically handed the town over to the Florentines without conflict. This event marked the end of the Sienese Republic. The entire town is walled with 14 imposing towers all around. Once in the castle, the main piazza opens up in front of you with the abbey of S. Maria Assunta, This buildings retains its medieval structure, as the rest of the village with its characteristic narrow streets.

As we started from Florence, Siena is the natural end of our tour. Siena is famous worldwide for its Palio –the breathtaking horserace in the main square-, the fantastic shell shaped piazza, -the Piazza del Campo- with its towering Torre del Mangia, the stunning Cathedral, and the countless noble buildings. Let's garage our classic car for a day and enjoy Siena walking.


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Drive in Style SaS
di Claudia P Morales H.
Indirizzo: Località Vallone 52044  Cortona, Arezzo, Tuscany
Tel:( 39 ) 0722 900111, Fax:( 39) 0722 90314, E-mail: info@driveinstyle.it


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