Something is missing in Tuscany. It’s mid-September: too late for the golden fields of sunflowers and too early for the glowing foliage of vines. Never mind, I settle for the serene views of hills capped with matronly hills, stone houses morphing into heads, and olive groves and vineyards into long coats covering the slopes. What’s obvious is the relentless work of men who turned a barren landscape of rocky soil and dense forests wrinkled by ravines into a groomed land of bounty.

Here, Chianti is King. Some of it might still be served from traditional flasks wrapped in straw and then perhaps recycled as candle holders but Chianti is a structured wine now. It must contain at least 80 percent Sangiovese—one of the world’s superstar grape varieties—for the Chianti Classico and 70 percent for the regular Chianti. Strict regulations have put an end to the often mouth-puckering wines of the past.

A Village with a Past

Our van claws its way up a rocky dirt road. The view from the renovated farmhouse we have rented is as expected. Olive trees and vineyards run down a valley. We are in Castellina, in the province of Siena, and at the heart of the Chianti where life unfolds, one meal, one glass of wine, and one moment at a time.

At 620 meters of elevation, Castellina in Chianti is the highest of the Chianti villages, a strategic advantage during the Florence and Siena centuries-long territorial feuds. What’s left of the Golden Age of the Etruscan civilization—Tuscany is a derivative of Etruscan—are the tunnels. Dominated by La Rocca, the tower that houses the archeological museum, they have been gentrified into via Volte, and tenanted by restaurants and artisan shops.

Castellina is the cradle of the original Chianti. For this reason, the Enoteca Antiquaria inside Palazzo Squarcialupi holds the archives of the Chianti Classico—with the black rooster emblem.

The medieval village is also the keeper of Lorenzo di Bicci’s 14th-century fresco of the Virgin Mary—which was “miraculously” spared in the San Salvatore Church, mostly destroyed during WWII. From there, the via Ferruccio becomes pedestrianized for a pleasant stroll to the Tourist Office, shops, restaurants, and outdoor stalls.

From One Chianti Village to the Next

Narrow roads, and their hairpin curves up and down the hills, lead to two villages and two wineries per day. It’s all that time and sobriety can muster, plus slow lunches. In some places, spitting is hardly an option when copious food is served as wine is generously poured.

It is soon apparent that the 14 villages under the Chianti appellation have much in common. First, they distinguished themselves with the words in Chianti following their names. Then they all have a church, an abbey, or a convent, palazzos, and of course, wine-tasting shops and quaint restaurants, most set amid what’s left of their fortifications. And true to the romanticized image of Tuscany, cypress trees punctuate the verdant countryside like exclamation marks.

A few facts give a distinctive touristic identity to these villages, enough for me to remember the essentials. But whether it’s a castle, church, painting, statue, or crucifix, every village seems to have something exceptional from time immemorial.

In Radda, it’s the peaceful setting of the town center and the elegant studio of a fashion designer next to a captivating gilding workshop. Along the cobblestones streets and stone walls, I wonder how many noble families lived here, at least as many as the number of hotels that bear the name Palazzo.

In Greve, the triangular Piazza Matteotti has been holding a Saturday market since the 13th century, tradition doesn’t die easily in Chianti, one butcher shop dates back to 1729. A photograph taken in the late 1800s shows the same arched portico alongside the piazza, now shading the outdoor dining and access to the tourist shops.  

In Castellina, we visit the Azienda Agricola San Donatino. I spoke French with Maria Cristina Diaz, the Spanish widow of Léo Ferré, a famous poet and singer whose Monegasque family has grown wine in Chianti since 1971. From this traditional under the Tuscan sun overlooking the valley, I imagine Ferré’s muse in the vineyard or among the 5,000 olive trees the family care for.

In Panzano, a hilltop situated halfway between Florence and Siena, the joviality of the annual wine festival has us overdo winetasting. I try to keep up with my fast-melting pistachio, lemon, and hazelnut gelato as we indulge in guessing who are the locals and the visitors among those on Vespas and in Fiats 500, only to find out they are rentals.

In Gaiole, we leave the SR222—the old Chiantigiana road—for the windy road to the 15th-century hamlet of Ama. There, two locations for wine and olive oil tastings illustrate two distinct lifestyles: the nobility of Castillo di Ama with its unusual open-air art collection and patrician setting, and the conviviality of Casanuova di Ama set in the dwelling of its former sharecroppers.

Perhaps because Ama means Love, our last day in Tuscany fills us with sweet visions of the dolce vita that hovers in each village.

What about the food, you might ask? Ah, after an Italian friend asked me to repeat aloud that I like Italian food better than French food—my native food—I had to hold the Chianti Classico responsible…  

Plump Sangiovese grapes growing in soft, clay-like soil (MCArnott)
In Chianti, terroir means wine and food. (MCArnott)
In the Ama hamlet in Tuscany (MCArnott)
A gilding workshop in Radda, Tuscany(MCArnott)
One iconic view of Tuscany (MCArnott)
Pouring by Maria Cristina Diaz at the Azienda Agricola San Donatino in Castellina (MCArnott)

Previously published 2012 – revised 2022