A Wine Journey from Florence to Sienna

So September is the grape harvest in Chianti, and in time for that I was sent this lovely email detailing a great path to follow from Florence to Sienna to really take advantage of all of the festivals going on in the Tuscan region.  While I won’t be able to fly out there and take experience this myself, I thought I would share it with my readers and if any of you do take the trip, I’d love to hear about it.

Here’s the email that was sent to me:

The Chianti area has been one of the most important wine producing regions in Italy for over two centuries. It was the family of the Grand Duke of Tuscany Lopold I that began cultivating grapes during the 18th and 19th centuries in the region that would become modern Chianti.

The Chiantigiana (SR 222) is one of the most scenic and charming motoring routes in Italy, running directly south from Florence to Sienna cutting through the heart of the Chianti Classico wine zone. The road sweeps around rolling Tuscan hills and past thousands of hectares of vineyards, all producing outstanding Chianti Classico DOCG (the highest classification of Chianti).

The best time of year to visit Tuscany (Toscana) is at harvest time in September, or just before harvest to see the vines bowing heavily with ripening Sangiovese grapes. During September most towns in Chianti celebrate the Sangiovese harvest with wine festivals such as the Vino al Vino held on the third week in September (17-19) in the small town of Panzano in Chianti, where many local wines can be sampled by the glass.

For a truly inspiring tour along Chiantigiana road, make time to visit some of the ancient towns of Chianti and surrounding vineyards. Most vineyards are open to the public, but it’s worth checking before you visit.

Greve in Chianti

Tuscan Wine MapGreve is a principle market town 31km south of Florence (Firenze).  During the second week of September, the Rassegna del Chianti Classico festival takes place in Greve.

Feste dell’uva
This is a wonderful festival held in the pretty village of Vagliagli. There will be a parade and dancing, lots to eat and drink

The Chianti Classico wine festival is also recommended and takes place between the 10 – 12 September.


Radda in Chianti is principle market town in the Province of Siena in the Italian region Tuscany, located about 35 km southeast of Florence and about 15 km north of Siena.


Gaiole in Chianti is principle market town in the Province of Siena in the Italian region Tuscany, located about 40 km southeast of Florence and about 15 km northeast of Siena. Forbes magazine named it number one in its list of “Europe’s Most Idyllic Places To Live.”

Whilst here, visit the Brolio winery. You can book wine tastings for small or large groups at the Brolio wine shop and learn about the Chianti Classico area through its most representative wines.


A small town with Etruscan origins, Panzano is situated on the Chiantigiana road between Castellina and Greve. The piazza is charming and a perfect place to sip a Prosseco.

The Vino al Vino wine festival takes place between the 17 – 19 September and there are a couple of winereies well worth a visit including Le Fonti and Fattoria Montagliari. The later has a fantastic restaurant with genuine Tuscan cooking and breath-taking views over the Greve valley.


Castellina  plays host to The Grape and Wine Festival during the third week of September.  A visit to the Villa Trasqua winery can be arranged wth a guided cellar tour and tasting session for 20 euros

Tuscan Villas in Chianti wine region

To make the most of the region’s excellent wine and local ingredients, it is recommend that you hire a villa. You have the freedom to cook up tasty Italian treats and relax on a veranda sipping local wine admitting the Tuscan countryside.

Villa Bernardi in Panzano in Chianti is a beautiful and spacious Tuscan farmhouse property situated on a hillside outside of the village of Panzano. The property dates back to the 11th Century and has been restored carefully to retain its original features and character. Laid out over 4 levels, this property is ideal for family groups with plenty of space to gather. The saltwater swimming pool is reached by a stone path across the lawn and enjoys views across the Chianti countryside. Sleeps up to 10 people and costs from £6552 per week

Or if there is just two of you, then the Panorama at Cornino in Castellina in Chianti is ideal. A spacious villa in the Hamlet of Cornino overlooking the Chianti hills, Panorama provides a peaceful retreat close to the town of Castellina. This beautifully restored property is surrounded by olive groves and unforgettable views. The property sleeps 3 people and costs from £546 per week.

To Tuscany has a wide choice of villas in Italy to choose from throughout the Tuscan wine regions. Visit www.to-tuscany.com to see a selection of properties and check availability.

About George Perry 884 Articles
A wine lover for as long as I can remember, I hope that my thoughts on wine can help others to make decisions on what they should drink as well.


  1. Thanks for all that info George. Planning on Tuscan vacation for retirement present, along with one for California. May hold off till Sept. 2011 for the Italian tour. Hope to spend 2-3 weeks, mostly in Tuscany.

    • My first thoughts on getting the info was how I could swing going…there’s no way though. Hope you have fun in both CA and Italy when you go.

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