Tuscany, warm fall in Chianti

Chianti, between Florence and Siena is an enchanting corner of Tuscany. A land full of history, nature, traditions, colours and flavours. Home of one of the world’s best-known wines, Chianti is an ideal destination for a fall weekend among its towns and villages full of atmosphere, surrounded by the scents of the grape harvest and traditional festivals.

Come and find out with us!

Our itinerary


We leave the motorway at Florence Certosa exit and take the state road number 2 near San Casciano Val di Pesa toward Greve in Chianti, the capital of its own valley.

The road winds on the hillsides, crosses wild areas covered by thick woods, goes up and down between rows of cypresses straight as shot, draws doodles between ordered vineyards and olive groves.

About twenty kilometers from the valley floor, past Montefioralle medieval village, we meet Greve in Chianti, a town with a little more than 13.000 inhabitants, whose center turns around the charming porched square, animated by the farm market every saturday morning. The row of stalls overflowing with fruit, vegetables, flowers and other farm products makes it particularly beautiful and reminds that Greve, on the route to Florence and on the edge of historic roads such as the Francigena and the Volterrana, has always played a role as an important commercial square.

Chianti Tuscany

But there is also the touch of art in Greve, inside the Santa Croce Church, where is conserved a precious XV century  triptych signed by the famous painter Lorenzo Bicci.

We continue southwards by the state road number 222, the historic Chiantigiana, which allows to visit two lonely parishes: San Leolino, XII century, with frescoes, painted tables, medieval majolica inside and a charming XIV century cloister, unique example all over the Chianti. And San Eufrosino Oratory, destination of nourished pilgrimages during the Middle Ages. 

After Panzano village, 7 km from Greve, we take the road number 429 that runs south and we admire the Volpaia Castle, a delightful village (XII century) surrounded by olive groves and vineyards, whose restorations have anhanced its poignant beauty.

Chianti Tuscany

Here, Chianti reveals one of its most exuberant profiles. The state road stretches between environments that become more and more wild and unexpected, with hills covered by thick woods, ideal habitat not only of the wild boar but also for the Cinta Senese, an aboriginal pig bred in the wild; with valleys, which resemble vertiginous little gorges, where the rays of the sun struggle to touch the earth. And the uninterrupted sequence of signs with the Black Rooster that reminds us that we are on one of the most famous wine roads in the world. A microcosm where wine is everywhere.

Chianti Tuscany

Radda in Chianti suddenly appears behind the last hairpin bend, perched on a hill from where ancient people could control the whole Valdarno.

Protected by thick walls, Radda was found, like all the Chianti, in the middle of medieval skirmishes between Florence and Siena, until, in 1384, it saw the rise of the Chianti League, with its own symbol the Black Rooster, a kind of autonomous jurisdiction, encompassing the Florentine countryside, with statutes and defensive powers.

The village is dominated by the fifteenth-century Palazzo del Podestà, which boasts a beautiful crenellated tower; while, just outside, the Franciscan Convent of Santa Maria al Prato is worth a visit, transformed into the Museo d’Arte Sacra del Chianti, on display are polyptychs, altarpieces and crosses from the Romanesque period.

Despite its modest size, Radda played a crucial role in wine and wine policy, as also a plaque under the portico of the Palazzo Comunale recalls: here, on 24 May 1924, The Chianti Classico Wine Consortium was born and all the most important decisions were made in terms of historical brand, promotion and marketing of this ruby nectar.

Chianti Tuscany

Our itinerary continues to the south, on highway number 429 and then on the road number 484, which open up fascinating views, pitting big architectural complexes, such as Badia a Coltibuono, a millenary abbey turned into a farm; Meleto Castle (XII century) just beyond Gaiole in Chianti and Brolio Castle, with its Italian Garden and a romantic park with precious arboreal essences. It was built on an isolated hill, on the slopes of the Chianti Mountains and from its walls, up to 16 meters high, the panorama is grandiose: on clear days, the view runs from Siena to Amiata to the mountains of Volterra. Today’s palace was built in 1860 by Bettino Ricasoli,called “the iron baron”, Prime Minister of the Kingdom of Italy and compiler of the first Disciplinary of Chianti Classic Wine.

The southern section of state road number 484 opens the last side of Chianti, accompaning us at the end of our itinerary.  A detour near Brolio allows us to admire the small streets and the old church of Borgo San Felice, a tourist complex nestled on a hill near Castelnuovo Berardenga, a stone’s throw from Siena. The careful restoration has made it a daydream, a destination for discreet and elite tourism, thanks to the high level of services and quality of the farm’s products.

The curious Chianti

Chianti Tuscany

Among the folds of this territory more unique than rare, there are places and curiosities that capture even the most distracted tourist.

** Between Castellina in Chianti and San Donato in Poggio, for example, rises the Fattoria La Ripa, now a winery, but once owned by such Lisa Gherardini married Francesco del Giocondo, universally known as La Gioconda.

Lisa inherited this and other properties from her father and how time was used, she gave it to her husband, a man much older than her. Thus, the present owners would live on the ancient possessions of the Monna  Lisa, a woman whom scholars have defined as a noble housewife dedicated to her children, devoted to God and her consort, but that Leonardo’s genius, portraying her with that enigamatic smile ( 1503 and 1506 d.C.), turned her into a real world star.

** On the hill of Pievasciata, a stone’s throw from Castelnuovo Berardenga, there is the  Chianti Sculpture Park, a permanent and open-air exhibition of contemporary works and installations. A magical place where nature and art interact perfectly, thanks to the creativity and sensitivity of artists from all over the world, who used the most disparate materials to create sculptures strongly integrated with the colors, the sounds and the light of the forest. The park also houses an Amphitheatre which, in summer, offers a rich program of concerts.

Chianti Tuscany

** Every year, at the beginning of autumn (this year, Sunday, October 6), Gaiole in Chianti becomes the spectacular setting of a two-wheeled event that is no less spectacular, L’Eroica, a non-competitive race on the white streets of the neighborhood, riding vintage bicycles and wearing old clothes. Gaiole in Chianti is the starting and ending point; the race provides two short routes (38 and 75 kilometers long); one medium (135 km) and one long ( 200 kilometers), of which 110 on dirt roads. More than a race, L’Eroica is a great festival among fans, and the 50 winners are people who have most immersed themselves in the spirit of the event.

**San Gusmè,  a few kilometers from Castlnuovo Berardenga, is one of the most ancient fortified village in Italy. Its walls, 500 meters long, enclose stone houses, a shop, two restaurants and the post office, the church of the patron Saints Cosma and Damiano and the Company of the SS. Announced with a characteristic bell tower. In short, an island of medieval small buildings suspended between a slope of vineyards and a forest of olive trees, where about three hundred inhabitants, the Sangusmeini, have decided to live happily in small, as one big family.

Chianti Turscany

**The symbol of the Black Rooster is an authentic travel companion, found along the roads, in the villages, behind every hairpin, everywhere. And if, on one side, it remembers, in addition to wine, also the intelligent recovery of an autochthonous breed of cockerel with black feathers and purple reflections; on the other side, it refers to the atavistic rivalry between Florence and Siena. Since the Middle Ages, these territories were being fought over. To put an end to the skirmishes and define the boundaries, the two cities decided to start, at the crowing of the cock, from their respective walls two knights who, galloping towards each other would set the border where they met. The Sienese people chose a white rooster and began to fill it with food in the belief that he might sing louder. The Florentines opted instead for a black cockerel that kept a cue and that, due to the hunger, on the day of the challenge, began to sing before dawn, allowing the Florentine knight to leave in advance of the Sienese one, succeeding to arrive in sight of the walls of the rival city and winning the Chianti.

The greedy Chianti, fall events

Chianti events

** Grape Festival , 29th September 2019, in Buondelmonti Square, Impruneta (Fi), the highlight is at 15.30 with the parade of the four historical districts’ floats, in a sparkling array of windows decorated with festive decorations, tastings and food stands.

** Not only Wine, 13th October 2019, Piazza Matteotti, Greve in Chianti (Fi), market exhibition with tasting of Chianti Classico wine and other typical products that characterize the territory; demonstrations of artisans at work, ancient games for the youngest and fans of vintage.

** Il Pagliaio in Greve in Chianti (Fi), 27th October 2019, a very lively market of organic and handicraft; an opportunity to taste flavors according to nature, fill the sideboards and discover handmade products. 

** Dit’unto, 13 October 2019, Villa in Sesta, Castelnuovo Berardenga (Si), lively gastronomic event for those who are not afraid to get their fingers dirty with traditional dishes; a festival that celebrates the genuine food and simple preparations of the Tuscan countryside, with an offer ranging from street food to starred restaurant.

How to reach Chianti

By car or motorbike, with the A1 Milano-Roma motorway, exit Firenze Certosa. From here, you can continue on the Firenze-Siena highway and exit at Poggibonsi, start point of the Chianti; or the state road number 222 more known as Chiantigiana, which winds along the hillsides and reaches the mentioned localities; or finally the highway number 2 Cassia. By plane, the closest and most convenient airport is Florence. By train, there are only two train stations in Chianti: Poggibonsi and Castellina in Chianti, both from Florence and Siena.




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