The most beautiful places in Chianti

The most beautiful places in Chianti are the four "classic" wine towns of Greve, Castellina, Radda, and Gaiole – along with little gems like Montefioralle, Panzano, and the fortified town of Volpaia. Chianti is one of Italy's most famous wine regions ; its hills, covered with vineyards, olive groves, and cypress trees, stretch between Florence and Siena.

The classic Chianti villages

Four municipalities lie entirely within the Chianti Classico growing region: Greve, Castellina, Radda, and Gaiole. In the Middle Ages, Castellina, Radda, and Gaiole formed the "Lega del Chianti," whose black rooster (Gallo Nero) is now the seal of Chianti Classico. Read more about the wine under DOC and DOCG in Chianti.

Greve in Chianti

Greve is the largest town in the Chianti region and lies roughly halfway between Florence and Siena on the Chiantigiana road (SR 222). Its centerpiece is the asymmetrical Piazza Matteotti with its arcades, wine shops, butchers, and cafés. A weekly market is held on Saturdays . Typical souvenirs include wine, olive oil , and cured meats from the region.

Montefioralle

Just a few minutes above Greve lies Montefioralle, a medieval fortified village of stone houses arranged in a ring. In 2022, it was named "Borgo più bello d'Italia," the most beautiful village in Italy. It's best to park below and walk the last few meters.

Panzano in Chianti

The small village of Panzano belongs to the municipality of Greve and lies above a valley basin filled with vineyards, known as the "Conca d'Oro" (golden basin). Numerous wineries offering tastings can be found in the surrounding area.

Castellina in Chianti

Castellina lies on a ridge between three valleys in the Sienese Chianti region. From here, there are sweeping views across the heart of the Chianti Classico area. Particularly charming are the Via delle Volte, a dark, covered walkway that encircles the town center, and the medieval Rocca in the middle of town.

Radda in Chianti and Volpaia

Radda lies further southeast, surrounded by walls, with Piazza Ferrucci at its center. The town has many small shops, wine bars, and restaurants and is quieter than Greve. The winding roads in the surrounding area are popular with motorcyclists and cyclists. A few kilometers north, the fortified village of Volpaia, with its castle, sits majestically – one of the most picturesque photo opportunities in Chianti.

Gaiole in Chianti and the Pieve di Spaltenna

On the way to Gaiole, you'll pass the Romanesque Pieve di Spaltenna, whose tower, with the cypress tree beside it, is a typical Chianti motif. Gaiole itself originated as a market town in the valley; in the main square stands a black rooster, the symbol of Chianti. Every year in October, "L'Eroica," a cycling race with vintage bicycles, starts here, taking place on the gravel roads of the Chianti region. Nearby, the old Badia a Coltibuono Abbey and the Ricasoli family's Castello di Brolio are worth a visit.

Tips for driving through Chianti

• Route: The Chiantigiana (SR 222) connects Florence with Siena via Greve, Panzano and Castellina – the classic panoramic road. Those who want to travel quickly should take the Florence-Siena expressway.
• Wine tasting: Many wineries offer tours and tastings, often only with prior booking. Those who drive must adhere to the 0,5 per mille blood alcohol limit.
• On foot: Beautiful hiking trails lead between the villages – tips can be found at Hiking in the Chianti.
• Best time: May/June and September/October (wine harvest); in midsummer it is hot and crowded in Greve and Castellina.

Background information about the region can be found under Chianti – in the heart of Tuscany , and the cities on the edge of Chianti in our city tours Siena and Florence.

Tours & Accommodation

• Tours and activities in Chianti – Winery tours with tasting, cooking classes in the vineyards and truffle hunting.
• Chianti wine and food tour from Florence – Guided excursion including visits to two wineries, practically without your own car.

Accommodation in the heart of Chianti can be found, for example, in Greve in Chianti (Booking.com).

Frequently asked questions about the most beautiful places in Chianti