The verdant swath of winding hills and country roads known as Chianti is what Tuscan dreams are made of. Silvery olive groves, lone cypresses, and an almond and green patchwork of tilled land form a gorgeous terrestrial tapestry. And, set among the rows of grapevines are medieval walls and Renaissance villas that seem to materialize in the morning mist.

A visit to Chianti is a great way to make the most of a trip to Tuscany. You can easily take a day trip from Florence, Siena, or Arezzo. Or, you can choose to spend your entire holiday here.

Chianti Location and Map

The wine region of Chianti—known as Chiantishire to some English speakers—is located in the middle of Tuscany, between the cities of Florence and Siena. The subregion is bounded by the Val di Pesa and Elsa River to the west and Chianti hills (Colline del Chianti) to the east.

Chianti was the first wine-growing region in the world to be defined by law. In 1716, Cosimo Medici III issued an edict declaring the boundaries of the Chianti district. In 1932, these boundaries were extended to define the wine production areas of Chianti Classico, a DOCG wine. DOCG is a classification that means that its origin is controlled and guaranteed by Italian law (in Italian: “Denominazione di Origine Controllata e Garantita”).

While the traditional, protected boundaries for the grape-growing region are between Florence and Siena (see the dark blue striped area below), Chianti production extends to include vineyards in the Tuscan provinces of Florence, Siena, Arezzo, Pistoia, Pisa and Prato.

User:Kattivik, CC BY-SA 3.0, via Wikimedia Commons

Most people who visit Chianti do so by car. The best route to follow is the SS222, also known as the Via Chiantigiana, which cuts a well-worn scenic path between Florence and Siena.

If you are not already traveling by car, it’s easiest to rent one in Florence, either at the counter at Santa Maria Novella train station or online via Europcar or Auto Europe.

You can also join a private tour or group tour to visit the vineyards. There are many Chianti tours from Florence that mix sightseeing with wine tasting, including the Medieval Castles & Chianti Wine Tasting Tour with Lunch and the Tuscany Day Trip From Florence With Chianti, Siena and San Gimignano. This is a great way to see Chianti so you’re not tempted to drink and drive.

For more athletic oenophiles, I suggest going on a Chianti Bike Tour with Wine Tasting.

Villages to Visit in Chianti

Chianti Classico Logos Black Rooster
Chianti Classico logos, old and new, with the famous black rooster (gallo nero)

The dozen or so small villages of the Chianti share a landscape, a similar heritage, and a stake in the production of fine Chianti Classico wine. A sense of history hangs heavy in the air here, but Chianti towns flirt with your senses rather than overwhelm you with obligatory itineraries.

If you’re driving from Florence, the first and largest Chiantishire town is Greve in Chianti (reviews). It is historically notable for being the birthplace of Giovanni da Verrazzano, discoverer of the New York harbor. In the middle of Greve’s Piazza Matteotti is a statue of the explorer and lining the square are arts and crafts shops, small restaurants, and wine sellers. Piazza Matteotti also hosts a farmer’s market on Saturdays.

Further south, smaller towns fan out along the SS222, the SS429, and the SS408 highways. The valley below Castellina in Chianti (reviews) was the site of fierce battles from the 12th to the 15th centuries when Florence and Siena fought over the strategically-located town. Its well-kept fortifications—the 14th-century Rocca di Castellina in Chianti, on the main square—has a crenellated tower from which you can admire the remarkable Chianti landscape. Inside the Rocca is the Archeological Museum of the Chianti Senese.

East of Castellina in Chianti is Radda in Chianti (reviews), the former capital of the Lega del Chianti, a medieval military alliance of Florentine principalities. The coat-of-arms of the Lega, the black rooster or gallo nero, was born in Radda. Today, the symbol lives on as the trademarked logo of the Chianti Classico Consortium. The Casa del Chianti Classico, located in the converted convent of Santa Mara del Prato, offers guided wine tastings, food, classes, and a store stocked with wine, accessories, and souvenirs.

Side Visit: Take a detour to the Chianti Sculpture Park to see modern art installations juxtaposed with the landscape of Tuscany

Wine Tasting in Chianti

Of course, no trip to Chianti would be complete without sampling the local wine. You can do so in a number of ways.

Visit a Vineyard

You need to make an appointment to visit most vineyards of Chianti. Check with Consorzio Chianti Classico for details and itineraries.

Go to an Enoteca

An enoteca is a wine store or wine bar that also sells wine by the glass and, sometimes, small plates of food. Some popular enoteche in the area are located in town, including Enoteca Falorni, Il Vinaino, and Enoteca del Chianti Classico in Greve in Chianti, and Enoteca del Chianti Bottega del Vino in Castellina in Chianti.

Wine and Dine

Trying Chianti Classico wine with the food that grows in its territory is the best way to enjoy it. Again, Consorzio Chianti Classico is the best place to look for info on restaurants in the area. In fact, there are quite a few Michelin-starred restaurants in Chianti among the 39 best restaurants in Tuscany.

Where to Stay in Chianti

Many wineries do double duty as vineyards and lodging, so you can plan a full Chianti vacation. Two places to consider are Castello Vicchiomaggio (reviews) and Badia a Coltibuono (reviews).

Browse the map below to find places to stay in Chianti that fit your style and budget:

Booking.com

In Conclusion

Chianti is a fantastic place to visit, whether for a day trip or for an entire holiday. And if you love wine, this is one of the most famous places in the world to enjoy it.

But, Chianti and Chianti Classico are not the only wines produced in Tuscany. Far from it! Learn more about wine routes in Tuscany for more itinerary ideas. And check out this page on Italian wine to find wines to try right now.