MagazineFive Beautiful Villages along the Chiantigiana Road

Five Beautiful Villages along the Chiantigiana Road

The Chiantigiana, less romantically known as the SR222, is a road in Tuscany that connects Florence and Siena and takes you on an incomparable road trip around the entire Chianti area. There are landscapes of rolling vineyards to see, and beautiful wineries to explore (we recommend checking out the quaint and charming Montefioralle winery near Greve at the start of your tour) – just make sure your driver doesn’t drink too much Chianti Classico along the way, otherwise you might be in for a bit of a risky ride! If you fancy interspersing your vino voyage with a few stops in some enchanting hilltop towns, there are plenty to choose from, so we’ve rounded up some of the best to make your decision a little easier.


Just outside the metropolitan hotspot of Florence is the small, tranquil town of Greve, which is also known as the gateway to the Chianti area. It’s got a lot of history to offer, with the nearby 13th Century Castle of Montefioralle, as well as the neo-classical Santa Croce Church and the Museum of Sacred Art, which features masterpieces such as a 14th Century depiction of the Annunciation. But it’s not all art and history in Greve, as like many other Italian towns, it is a perfect pit stop for food and vino (it is in the Chianti area after all!) Lining the main square (or should we say triangle due to its irregular shape?) is a portico that features many artisanal shops and restaurants, including the Antica Macelleria Falorni, a butcher that has been in the same spot since 1729!

A view of Chianti Hils


If you’re interested in the infamous feud between the city-states of Florence and Siena, then Panzano is the perfect pitstop along the Chiantigiana for you. It’s located almost precisely in the middle of the once warring powers, so found itself repeatedly destroyed during the fighting. The village, however, has risen like a phoenix from the ashes and boasts beautiful reconstructed architecture for you to see, such as the Church of Santa Maria, which was rebuilt in the 19th Century. If you fancy sampling some of the local delicacies during your visit, head to the famous butcher’s Dario Cecchini for a traditional Florentine steak, or, if you’re there in September, make sure you don’t miss their famous wine festival “Vino al Vino”!



Not only an important stop along the Chiantigiana due to being the birthplace of the Chianti Classico Consortium in 1924, but Castellina is also another hotspot for the history of the Florentine-Sienese war. Dating back to the Etruscan period, the town was fortified by the Florentines in the 15th Century to act as a defensive outpost against their rivals, and therefore the architecture has the feel of a medieval military fortress. The town’s hexagonal defensive wall is still visible today, even after being repeatedly destroyed and rebuilt during the fighting! To be transported back to the middle ages, take a walk down the Via Delle Volte, which was a tunnel used by the town’s guards but is now a covered street filled with shops and restaurants, or visit the 15th Century fortress build just outside the town, which is now home to the Archaeological Museum of Chianti.



Want to start combining your historical tour with a nice big helping of vino? Then make your way to Volpaia, a historic village dating back to 1152 with wine running through the heart of it – literally, as a network of pipes transport wine across various buildings that comprise the winery! The winery, which takes up 2/3 of the village is currently owned Giovanella Stiani, whose father originally bought the site as a hunting ground. But now, the village has been transformed into an enchanting paradise, where wine lovers can stay in accommodation overlooking rolling vineyards, and take part in winery tours, where they’ll discover Vin Santo drying hooks, wooden oak barrels and metal fermenting tanks (which enjoy their home in a 15th Century chapel!) carefully concealed behind 12 Century walls and covered in naturally occurring caper flowers. After enjoying a tour of Volpaia winery and tasting their beautiful selection of products ranging from Chianti Classico to sweet Vin Santo, you probably won’t be wanting to head back on to the SR222 any time soon. So it’s a good job Volpaia have accommodation for vino gluttons to rest in!


Some may know this town as the home of certain characters from Assassins’ Creed, but there’s a lot more to Monteriggioni than its links with the famous PlayStation Game. Known for its medieval fortifications and watchtowers, Monteriggioni was a defensive town for the Sienese during the troubles with Florence, and you can see why it was such a good vantage point when you walk upon the old walls – you can see for miles across the breath-taking Tuscan countryside! A ticket to walk on the walls will also gain you entry into the intriguing armour museum, which houses faithful reproductions of weapons and armour from the Medieval and Renaissance periods, some of which you can even try on yourself!

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