Grape Harvest along the Chianti wine trail: From Florence to Siena

The Chiantigiana (SR 222), the road connecting Florence to Siena, is one of the most beautiful  routes in Italy, passing the vineyards producing the world-famous Chianti Classico DOCG. 

Chianti has been one of Italy’s most important wine-producing regions for more than three centuries after the Grand Duke of Tuscany began cultivating grapes during the 18th and 19th centuries in the region south of Florence. Now the Chianti region that covers 70,000 hectares between Siena and Florence, is worldwide famous for wine production. The so-called Chianti Classico is a special type of Chianti wine produced in the municipalities of Greve in Chianti, Barberino Val d'Elsa, San Casciano and Tavernelle in Val di Pesa.

The Chianti classico wine boasts the DOCG label which guarantees the quality and and origin of the wine. Not only must the Chianti classico wine be produced in certain municipalities (see above for the list), but also it must be prepared with at least 80% of Sangiovese grapes, the typical red variety of the region.

Not only red wine, but also extra virgin olive oil is another must product to taste while travelling around the pictoresque streets of the region. If you need a break from the busy streets of the city, a trip to Chianti is a great idea!

The best time of year to visit Chianti is during the September harvest or just before to see the vines bowing under the weight of the ripening Sangiovese grapes – the variety from which Chianti Classico is made.

Another good reason to visit in September is to join in one of the local festivals that celebrate the harvest, such as the Vino al Vino, held on the third week in September, in the small town of Panzano, where many local wines can be sampled by the glass.

For a truly inspiring tour of the Chiantigiana, take the time to visit some of the ancient towns along the way and call by the vineyards. Most wineries are open to the public, but double check before you visit to avoid disappointments. Here are some of our favourites:



Greve in Chianti

Greve, one of Chianti’s main market towns, oozes history, from its Franciscan monastery in the old quarter to the market on the triangular main piazza, where traders have been selling their wares down the centuries.

Wineries to visit:

Castello di Verrazzano: Visit the vineyards and cellars of this ancient castle, dating from the 12th century, to taste classic wines, olive oils and balsamic vinegar. There are lovely late-Renaissance gardens to stroll around, too.


The winery at the villa of Vignamaggio, which dates back to the 14th century, produces Chianti Classico, Chianti Classico Riserva IGT and Vinsanto del Chianti Classico DOC. Pre-book a guided tour of the gardens and cellars, including a wine tasting and lunch. If you’re tight for time, just pop in the shop to sample the wine and olive oil.

Panzano in Chianti

This small town between Castellina and Greve, first settled by the Etruscans, is overlooked by an 11th-century castle, a hike to which, through the cobbled streets, is well worth the effort. The town’s piazza is charming – a place to while away time watching the elderly locals playing cards while sipping a Prosecco or enjoying home-made gelato.

Wineries to visit:

Le Fonti - Le Fonti, a charming, boutique, family run winery set at the foot of Panzano, is open for cellar tours and tastings of its superb IGT and Chianti Classico DOCG.

Fattoria Montagliari - A small family run farm, Fattoria Montagliari has been producing wine using traditional methods since 1720. The Migliorini family, who bought Fattoria Montagliari in 1999, are the latest to cultivate its soil, producing Chianti Classico DOCG, Chianti Classico Riserva, Brunesco di San Lorenzo IGT, grappa, brandy, extra-virgin olive oil and aged Trebbiano balsamic vinegar. There is also a fantastic restaurant here, serving up authentic Tuscan cooking and beautiful views of the Greve valley.

Castellina in Chianti

Castellina in Chianti is a sight to behold, sitting on its high ridge. It is thought to have been built on the ruins of a Roman settlement. But it’s the 14th-century fortress and the 16th-century church of San Salvatore that today’s visitors come to admire.

Wineries to Visit:

Gagliole: What’s your tipple, Chianti Classico or grappa? Both (and more) are on the tasting menu at Gagliole, a vineyard dating back to the ninth century.

Villa Trasqua: This vineyard offers guided tours of its cellars, including tastings of Chianti DOC and IGT wines.

Radda in Chianti

The ancient market town of Radda has been key to Chianti’s fortunes and remains a community immersed in the wine industry. Stroll the cobbled streets to trace this town’s history down the centuries, in the old town walls, the Palazzo del Podesta, and the Propositura di San Niccolo.

Wineries to Visit:

Volpaia: Find out about the long tradition of winemaking in this restored hamlet, where wine tastings will take you from grape to bottle.

Castello di Albola: High in the Chianti hills, an amphitheatre of vineyards provides the grapes for some great wines that you can try if you drop by.

Gaiole in Chianti

Call by charming Gaiole and you’ll soon realise why the American magazine Forbes put this charming town at the top of its list of Europe’s Most Idyllic Places to Live. Yet, Gaiole is more than a pretty face. It was once a powerful community, one of the centres of the Chianti League.

Wineries to visit:

Castello di Brolio: The biggest winery in Chianti Classico, Barone Ricasoli has been linked to wine since the 12th century, when Brolio Castle passed into the hands of the family of this name. Learn about and appreciate the fruits of these vines on a selection of tours, including one held at sunset. You can take a closer look at parts of the Neo-Gothic castle, too.

Casanuova di Ama: Casanuova di Ama was bought by the Bencini family in 1967. For the following 20 years, they restored the estate’s buildings and planted new vineyards before finally putting their first wine on the market in 1984, sold in the iconic traditional fiasco, the bottle with a rotund bottom wrapped in straw.


If not in Tuscany, do come visit us in Singapore’s Cluny Court and Paragon where our new autumn collection has just arrived!

With sunny greetings from Italy and „alla prossima volta“!



Alfie Browns

Kian K