Montespertoli

The territory of the present-day municipality of Montespertoli, in the province of Florence, has ancient roots: as far back as the Etruscan period, the Via Volterrana ran through these hills from north to south, enabling Florence to conduct trade towards Volterra and Siena, and connecting with the Via Francigena near Certaldo. From the Early Middle Ages onwards, Florentine nobility multiplied their settlements along this route, and great families — the Acciaioli, Guicciardini, Machiavelli, Frescobaldi and Strozzi — left behind a legacy of castles, parish churches and villas that can still be encountered today along the white gravel roads between the vineyards.

Today, Montespertoli is known above all as one of Tuscany’s capitals for Chianti wine: the agricultural landscape — gently rolling hills covered with vineyards and olive groves, punctuated by rows of cypress trees — is quintessentially Chianti Fiorentino, and the territory’s wine production is of outstanding quality, with the designations Chianti Montespertoli DOCG and Chianti Colli Fiorentini. The municipality is also renowned for the production of white truffle, so much so that it is known, together with nearby Montaione, as the City of the Truffle. A peaceful, seemingly sleepy municipality that conceals a concentration of history, art and flavours far beyond what one might expect.

Things to do in Montespertoli

Montespertoli and its hamlets offer a rich route through medieval castles, Romanesque parish churches and museums of surprising quality. The key to appreciating the territory is to move slowly, preferably by car or bicycle, along the secondary roads connecting the various villages.

Montegufoni Castle

A few kilometres from the town centre, along the Via Volterrana towards Florence, you’ll encounter Montegufoni Castle, one of the most fascinating historical buildings in the area. Originally a medieval fortress, the castle passed to the Acciaioli family at the end of the thirteenth century and became celebrated as the birthplace of Niccolò Acciaiuoli (12 September 1310), Grand Seneschal of the Angevin Kingdom of Naples, close friend of Boccaccio and Petrarch. Between the seventeenth and eighteenth centuries, the complex was thoroughly restructured by the family in the style of a grand Baroque villa; the tower with its balcony recalls that of Palazzo Vecchio.

The castle’s twentieth-century history is equally fascinating: acquired by Sir George Sitwell, an eccentric English aristocrat, it became the headquarters of the Sitwell family — including his children Edith, Osbert and Sacheverell, prominent figures in twentieth-century British culture. In 1921, Sir George commissioned Gino Severini to create the frescoes in the Sala delle Maschere (Hall of Masks), featuring masks, harlequins and owls in vivid colours. Legend has it that his children had suggested an alternative young painter — Pablo Picasso — but the father preferred Severini. The Church of San Lorenzo within the complex houses a crucifix by Taddeo Gaddi from the mid-fourteenth century, among the most important pieces in the entire territory. Today the castle operates as a hotel and resort, with the gardens open to visitors.

Sonnino Castle

At the entrance to Montespertoli stands Sonnino Castle, the fortress that for centuries gave its name to the family of local lords. The complex once belonged to the Conti Alberti da Mangona, then in 1393 — when their line died out — passed to the Machiavelli, who owned over two-thirds of the surrounding territory and donated numerous works of art to local churches. In 1830 it was purchased by the Sonnino family, who still own it today: the most celebrated name is that of Sidney Sonnino, Italian Foreign Minister in 1914 and twice Prime Minister. The medieval complex retains a thirteenth-century tower; today the estate produces Chianti wine and is open for guided visits and tastings.

The Church of San Piero in Mercato and the Museum of Sacred Art

About 2 km from the town centre, in the hamlet of San Pietro in Mercato, stands the Church of San Piero in Mercato, the principal religious centre of the area throughout the Middle Ages, documented from 1008 and consecrated in 1057. The structure retains its original three-nave Romanesque layout, with a fine baptismal font from the twelfth-thirteenth century in the Florentine Romanesque tradition. The façade in imitation white and green marble is the result of early twentieth-century restoration work.

In the adjacent presbytery is the Museum of Sacred Art, inaugurated in 1996 as a repository for works from churches throughout the territory that were no longer sufficiently secure. The museum is organised in four rooms following the parish church tradition and houses paintings, gold work, vestments and wooden furnishings of considerable value: among the masterpieces are works by Cenni di Francesco di Ser Cenni, Ugolino di Nerio, Meliore, Neri di Bicci and a Madonna and Child from the workshop of Lippo di Benivieni from Montegufoni Castle. The museum is part of the Terre degli Uffizi network, a project that brings the excellence of the Bargello and Uffizi museums to small museums throughout Tuscan territory.

The Museum of the Vine and Wine

In the centre of Montespertoli is the Museum of the Vine and Wine run by the “I Lecci” wine culture centre, which illustrates all stages of wine production through period instruments, educational panels and reconstructions. The route includes a Laboratory of the Senses where you can test your ability to identify flavours and aromas, and a wine shop where you can taste local wines paired with typical Tuscan dishes. It’s an ideal stop for those wanting to deepen their understanding of Chianti culture before venturing into the territory’s wineries.

Poppiano Castle

A few kilometres from the town centre stands Poppiano Castle, owned by the Guicciardini family since 1200 — a continuity of ownership spanning over eight centuries, rare even for Tuscany. The castle, still inhabited by family descendants, is surrounded by vineyards and produces quality Chianti wine. It’s possible to visit the cellar and participate in tastings by contacting the estate directly.

The Chianti Exhibition

The most anticipated event of the year in Montespertoli is the Chianti Exhibition, one of Italy’s oldest wine festivals: in 2025 it reaches its 67th edition, held each year between the last week of May and the first week of June, animating the village’s squares and streets for an entire week. The programme alternates guided tastings of wines from local wineries, food stands with local specialities, concerts, street theatre performances, the Contrade Tournament and historical costume parades. It’s the best opportunity to experience Chianti Montespertoli DOCG directly from producers, in a festive and genuinely popular atmosphere.

Montespertoli’s events calendar is full throughout the year: in June the Wild Boar Festival, in July the Ficattola Festival (fried bread with cured meats), on 18 August the feast of patron saint Sant’Ilicino Martire, and in November weekends dedicated to new wine, new oil and truffles.

Where to stay in Montespertoli

Accommodation in Montespertoli is concentrated mainly in farm stays and farms throughout the territory, many with their own wine and oil production. It’s the ideal solution for those wanting to immerse themselves in the Chianti Fiorentino landscape without sacrificing the comfort of modern facilities. Montegufoni Castle houses a hotel with rooms in the castle’s historic chambers. For those seeking something more central, in the village of Montespertoli there are several B&Bs and holiday apartments at reasonable prices compared to Florence’s facilities, with the added benefit of being less than 30 km from the city.

Recommended hotels in Montespertoli

How to get to Montespertoli

Montespertoli is about 31 km from Florence, reachable by car in 35-45 minutes depending on traffic. The fastest route is the A1 motorway to the Firenze Scandicci exit, then the Florence-Pisa-Livorno dual carriageway towards Empoli, exiting at Ginestra Fiorentina, from which you follow signs for Baccaiano and Montespertoli (about 10 km). The alternative route — slower but far more scenic — is the Via Volterrana from Galluzzo, which runs through the Chianti hills via Cerbaia and Baccaiano.

By bus, Montespertoli is connected to Florence, Empoli and Certaldo by coaches from PIÙ BUS, with several daily services. Those arriving by train can alight at Empoli station (17 km) and continue by bus or taxi. Florence Santa Maria Novella station is 31 km away.

Montespertoli Weather