Though it can feel a little trite to say that Tuscany is a “state of mind,” there’s no denying that here, regional borders are rough at best, and precise geographical boundaries can be elusive. The “Chianti Classico” area is better defined than many of its counterparts, though, due mostly to boundaries delineated by Cosimo III de’ Medici in the eighteenth century, which he drew to create a clear area for wine producers here. But in true Tuscan fashion, today’s towns’ relationships feel more rooted in shared history than strict geography. The most expansive subsection of the greater Chianti area, the “Chianti Classico” is perhaps best described as the “heart” of Tuscany, spanning the hilly lands between Florence and Siena and encompassing parts of both provinces. Beyond our own charming location in Vagliagli, a short drive from Siena, here are five towns in this classic region worth checking out.
Many travelers to Italy know that the Boot has many different faces—but still, plenty of people have a postcard-perfect image of the “Italian countryside” in mind. If you’re looking for a trip full of Tuscan trademarks, Castelnuovo Berardenga is a cut above. It is also home to a wine consortium of which Dievole is part – it’s the nearest large town to our property, in fact. This town, which is believed to date back to Etruscan times, features incredible gardens, fairytale-like castles such as Villa Sesta, and numerous churches and monuments. Medieval history buffs will appreciate it as the site of the thirteenth century Guelph versus Ghibelline Battle of Montaperti, which was mentioned in Dante’s Divine Comedy.
In a region as romanticized and written about as the Chianti Classico, Poggibonsi is about as far off the proverbial “beaten path” as you can get—and trust us, this is still pretty far off! Poggibonsi’s at times industrial aesthetic presents a nice contrast with the olive groves and vineyards that make up its quintessentially Tuscan landscape. Located in the province of Siena, it’s admittedly not as picturesque as its capital counterpart, but you’d be hard pressed to find any tourists when strolling the streets. That’s not to say there’s nothing to see: the Gothic Basilica of San Lucchese is one of Tuscany’s little-known treasures, housing a striking sculpture by Giovanni della Robbia. A local must-stop is the Fonte delle Fate (the ‘Fairies’ Spring’), a fountain and the only remains of the medieval town of Poggibonizio. Check out the contrast with the contemporary I Dormienti, an eye-catching sculpture series by noted Italian artist Mimmo Paladino, installed next to the thirteenth century fountain in 2000.
Radda in Chianti
Back on a bit more beaten track, Radda in Chianti is one of the crown jewels of the Chianti Classico area, meeting and exceeding travelers’ expectations of what Tuscany “should” look like while also maintaining its own character and vaunting a variety of attractions. Visit the Propositura di San Niccolo’, a Romanesque parish church with a curious Neo-Gothic facade, or the Palazzo del Podestà, adorned with marble and terracotta family crests. Next, if you’ve been busy exploring crowded museums in Siena or Florence, stopping in at the quietly captivating Chianti Sacred Art Museum will be a breath of fresh air. Housed in former Franciscan convent Santa Maria in Prato, the hidden museum features Florentine and Tuscan painting spanning several centuries, along with church vestments and eucharistic vessels. After the whole day sightseeing, stop at the Casa Chianti Classico in Radda both for wine tasting and for their interesting small wine museum.
Gaiole in Chianti
Though this town is nothing short of serene, it’s perhaps best known as the starting point and birthplace of L’Eroica, the world-famous cycling event that takes bikers on one of the world’s premier “scenic routes”—through Montalcino, the Val d’Orcia and the Crete Senesi, as well as onto Dievole’s property, then circling back to the heart of Chianti. Though the race is only an annual event, serious bikers can take the route any time of year, so when you tire of wine tasting (if that ever happens) and crave something more strenuous, get pedaling in Gaiole in Chianti! If art and history are more your speed, the town is home to various Romanesque parish churches. A highlight, though, is the Brolio Castle outside of town, a hilltop home that’s stayed within the prestigious Ricasoli family since medieval times.
Greve in Chianti
Good old Greve is the obligatory “household name” in this list, and for valid reasons. It’s famous the world over for its Expo del Chianti Classico, a huge wine festival that’s been running for nearly half a century. If you can’t swing a visit in early September, when that sacred wine-lovers weekend is usually held, Greve is still worth your while. Make the hike up to Montefioralle, a hilly medieval hamlet that may lure you away from city life forever. Prefer to stay downtown? Spend an afternoon in piazza Matteotti, Greve’s lively central square, lined with butcher shops, coffee hideaways and booths of bric-a-bracs. Stop by on a Sunday if you can: unlike many sleepier Tuscan towns, Greve frequently hosts pottery and craft markets and workshops, making it perfect for a family day trip.