The SR 222 (Strada Regionale 222 is the official name of the Chiantigiana Wine Road) connects all the main towns of Chianti: Greve in Chianti, Montefioralle, Panzano in Chianti, Castellina in Chianti, Radda in Chianti and Gaiole in Chianti. It cuts through scenic hills, olive groves and vineyards and leads you through little medieval villages with stunning churches and castles. The Chianti region is first and foremost famous for its wine and wineries. On your explorations down the Chiantigiana make sure to include a stop for some wine tasting.

An itinerary in the heart of Chianti

The Chiantigiana is 74.9 km long and connects Florence to Siena. Part of the magic of a road trip in Chiantishire is testing out little roads on a whim and ending up in some unexpected place. You can’t really go wrong, there is always something beautiful to see and tasty to eat around the bend.

If you are more of a planner or just short on time, follow this guide of the most important Chianti towns. This itinerary starts from Florence. After reading this article you will be looking forward to explore Chianti by yourself (but be aware of drinking and driving laws in Italy) or by a guided wine tour.

The map

Greve in Chianti

Piazza del Mercato in Greve in Chianti
The statue of Giovanni da Verrazzano, whose name is familiar to every New Yorker, in Greve’s main’s square Piazza Matteotti.

Greve in Chianti is 39 km away from Florence and the main town in the Florentine part of Chianti. Every September, it hosts the biggest wine fair in the area called La Rassegna del Chianti Classico. The main square is Piazza Matteotti, where the Saturday morning market is held. If you observe the square carefully, you will notice that all the porticoes are different sizes and sometimes even materials. The merchants of the city paid for their construction out of their own pocket which explains the lack of homogeneity. The statue in the center of the piazza commemorates Giovanni da Verrazzano, one of the first Europeans to explore North America. The explorer is considered a Greve inhabitant even though the Verrazzano castle is out of the town proper.

Art lovers may want to make time for the San Francesco museum of sacred art. The museum is only open from 4 p.m. to 7 p.m. on Tuesdays, Thursdays and Fridays . Saturday and Sunday, it accepts visitors from 10 to 1 p.m. and from 4 to 7 p.m. Here’s its website.

Montefioralle

View of Montefioralle in a sunny day from vineyards surrounding it
Montefioralle lies among vineyards under the Tuscan sun.

Get off the SR222 for a small detour to Montefioralle. This little medieval hamlet is only 5 minutes away from Greve in Chianti and well worth a visit. The road up the hill has a few switchbacks and is quite narrow, so drive slowly and enjoy the views, Montefioralle, with its stone houses and fortified walls, looks like it hasn’t changed much since it was founded in the 12th century. The town was built around the castle and expanded elliptically around it. Most of Montefioralle’s fortifications are still standing.

Fun fact: another famous explorer, Amerigo Vespucci (from which America takes its name), owned a house there.

Panzano in Chianti

A view of Panzano in Chianti from outside the city
Hills, cypress and sun: are you in a watercolor or in sunny Tuscany?

Food and wine lovers should include a stop in Panzano in Chianti. Back on the Chiantigiana, take a right turn onto Via della Conca d’Oro and drive up to other little medieval town. The Panzano castle is quite a sight to behold with its beautiful stone towers and loggia terrace. Sadly, the castle can’t be visited because it has been transformed into private residences.

The real treasure of Panzano is the Conca d’Oro, or the shell shaped valley that surrounds the town. Panzano is a great place to enjoy breathtaking views of the Tuscan landscape with its forest, olive groves and vineyards. Wine is at the center of the Vino al Vino festival held in mid September. It’s the perfect opportunity to sample the local Chianti wine production.

Castellina in Chianti

The Rocca of Castellina in Chianti, a medieval castle in a sunny day
The Rocca of Castellina in Chianti: Castellina was a military outpost of Florence.

Castellina was a crucial Florentine military outpost in the war between Siena and Florence (1552-1559). The fact that Castellina is much closer to Siena, than it is to the region’s capital, gives an idea of the expansion of Florence at the time. If you want to immerse yourself in the medieval atmosphere, head to Via delle Volte. This arched stone passage follows the eastern outer city walls. You can peek out of the arrow slits and admire the panorama of the Chianti countryside. Via delle Volte is one of the few remainders of the fortified wall perimeter. Most of it was destroyed during various battles throughout history.

Castellina is also famous for a big Etruscan tomb called Montecalvario. The knoll hosts four burial chambers. The monument is open to the public and free of charge. In order to see in the dark press the light switch at the entrance. Beware, the light is on a timer and you could end up in the dark when you least expect it! The ground can also get quite muddy after heavy rains.

Radda in Chianti

A small sunny corner of Radda in Chianti
Radda in Chianti city center: historical monuments and medieval streets.

From Castellina in Chianti, backtrack on the Chiantigiana until you get to the turnoff for the SR 429 (Strada Regionale 429). You will reach Radda in about 15 minutes. This charming town on a hill was founded by the Etruscans. It then served as the capital of the Lega del Chianti, a military alliance affiliated to Florence during the Florence-Siena wars. Once the conflict ended, the noble families and land owners of Radda focused their energies on the production of wine. Radda has been actively producing this beloved beverage for the last 5 centuries!

If you want to discover the Chianti countryside differently, come to Radda in March for the Chianti Ultra Race. Radda organises three races of different lengths (15k, 42k, 73k) on trails around the vineyards of the area.

Gaiole in Chianti

Brolio Castle in Gaiole in Chianti
The Brolio Castle has belonged to the Ricasoli family since 1141.

Continue on the SR 429. At the crossroads take a right turn onto SP 2 (Strada Provinciale 2 di Molilungo). The drive is only 15 minutes long. Gaiole in Chianti, helped by its strategic position near many important roads, was a bustling market town in the Renaissance. The town, just like Radda, was also part of the Lega del Chianti. Unlike most of the other towns in Chiantishire, Gaiole isn’t fortified. But don’t be disappointed, there are at least four incredible castles to visit nearby: castello di Lucignano, castello di Meleto, castello di Ama and castello di Brolio. This last one, owned by the Ricasoli family, has been destroyed and rebuilt so many times that is has become a compendium of different architectural styles. In 1835, the baron Bettino Ricasoli had his medieval castle transformed in the neo-gothic style very much in vogue in England at the time. The very same baron was instrumental in creating the recipe for the Chianti wine we enjoy today. The garden and a small museum are the only places that can be visited for the entrance fee of €5 and €8 respectively. Both include a wine tasting.

The Chiantigiana is the best way to enjoy the Chianti area at a slow pace and without the typical flocks of tourists. The charming little towns that dot the hilly landscape are perfect for short stops, a bite of delicious food and a glass of red.

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