Tenuta Castiglioni: A Thousand Years of Frescobaldi Wine

Twenty kilometers southwest of Florence, on the gentle hills of the Chianti Colli Fiorentini, stands an estate that has been producing wine for longer than most countries have existed. Tenuta Castiglioni is where the Frescobaldi story begins and the Frescobaldi story is one of the most extraordinary in the history of wine.

The Family Behind the Wine

Before they were winemakers, the Frescobaldi were bankers. A prominent Florentine family from the 12th century, prominent in business and politics, they built their fortune through banking, the wool trade, and an extraordinary willingness to lend money to European monarchs. Between 1302 and 1310, the Frescobaldi loaned £150,000 in English pounds sterling to Edward I and II of England, a sum equivalent to several times the annual revenue of the English crown at the time. In return they were given virtual control of the revenues of England, including the mint and the customs, and were granted lands, honours, and privileges.

It ended badly, as these arrangements often did. Edward II’s barons grew increasingly jealous of the Italians’ power and drew up ordinances forbidding the assignment of customs to foreigners. Seeing the way the wind was blowing, the family head fled England, first to Avignon and then to Florence. The royal debt was never repaid, and they went bankrupt. This was the end of their banking career.

But not the end of the Frescobaldi. They turned to wine.

The Frescobaldi family began producing Tuscan wine in 1308 and soon developed a notable client base. In exchange for paintings, the Frescobaldi traded their wine with Michelangelo. Later they supplied wine to Henry VIII, surviving contracts in the family archives are signed by the English king.

This is a family that has been at the centre of European history for a thousand years. They donated land for the construction of the Basilica di Santo Spirito, Filippo Brunelleschi’s final major work. A Frescobaldi poet, Dino, was a close friend of Dante Alighieri and, after reading the first seven cantos of the Divine Comedy, encouraged Dante to continue writing his epic poem.

Their wine archives, preserved in the family home at Remole near Florence, document an unbroken history of production that spans seven centuries.

Tenuta Castiglioni: Where It All Began

The Frescobaldi family owns six estates across Tuscany today. Tenuta Castiglioni, in the Val di Pesa near Montespertoli, is the oldest and most historically significant. The first document attesting to the existence of the Tenuta Castiglioni dates back to 1092, whilst Berto Frescobaldi’s will, in 1331, mentions the presence of “lands with vineyards” on the estate. Another important document about Castiglioni is the geographical map painted by Ludovico Buti in 1509, and preserved in the Uffizi Museum in Florence.

The property stands on the ancient Via di Castiglioni, built by the Romans to connect the north of Tuscany to Rome. Wine has been made here, in one form or another, for at least a thousand years.

The estate today covers 513 hectares, of which 148 are vineyards. The position is particularly favourable: a mild climate, gently caressed by the constant sea breezes that soften the temperature both in summer and winter, cleansing the sky and intensifying exposure to the sun. The soil is rich in clay, guaranteeing generous water retention that prevents the vines from suffering drought and allows the grapes to ripen harmoniously.

The grape varieties planted here Cabernet Sauvignon, Merlot, Cabernet Franc, and Sangiovese reflect both the ancient Tuscan tradition and the international outlook the Frescobaldi have always maintained. A family that was selling wine to the English crown in the 14th century was never going to be parochial about viticulture.

The Wines

Giramonte is the estate’s flagship wine, produced in small quantities and representing the best of what Castiglioni can do. A Toscana IGT based primarily on Merlot with a small percentage of Sangiovese, it is the wine the Frescobaldi make when they want to show what this particular corner of Tuscany is capable of. Intense ruby red, with notes of blackberry and thyme giving way to coffee and cocoa. A wine for serious occasions and patient cellars.

Tenuta Frescobaldi is the estate’s signature wine and the most widely known: Cabernet Sauvignon, Merlot, Cabernet Franc, and Sangiovese in a blend that is unmistakably Tuscan despite its international grape varieties. Ruby red, with red berry fruit, cocoa, coffee, and light notes of violet. Deep and persistent on the palate. This is the wine that sits on the table at a long dinner and keeps getting better.

Castiglioni Chianti DOCG is the everyday wine and in Tuscany, a good everyday wine is not a small thing. Sangiovese with a little Merlot, strawberry and raspberry on the nose, floral notes of rose, well balanced and food-friendly. The kind of bottle you open without ceremony and finish without regret.

The estate also produces Laudemio, the Frescobaldi extra virgin olive oil, made from the olive groves that have surrounded these vineyards for as long as the vines themselves.

Montespertoli and the Chianti Colli Fiorentini

The town of Montespertoli, near which Castiglioni stands, is one of the small capitals of Tuscan wine. The Chianti Colli Fiorentini denomination surrounds Florence on its southern and western sides — a wine zone that has historically supplied the city with its everyday wine, as these hills have done for centuries.

The area sits not far from the Via Francigena, the ancient pilgrim route that connected Canterbury to Rome through France, Switzerland, and central Italy. The Montespertoli Chianti Wine Route today follows a similar path through medieval hamlets, castles, and local food and wine specialities including a Wine Museum dedicated to Chianti and the Mostra del Chianti Montespertoli, a wine festival running every May and June for more than sixty years.

This is not the Chianti Classico of the famous hilltop villages between Florence and Siena. It is less well-known, less visited, and for exactly those reasons often more interesting to explore. To understand how this wine zone connects to Florence and its history, read our guide to the Chianti Colli Fiorentini and the wine windows of Florence

Visiting Tenuta Castiglioni

The estate is approximately 30 kilometres from Florence, in the Val di Pesa. It is reachable by car in under an hour from the city centre. The estate receives visitors for tastings and offers the opportunity to try not only the Castiglioni wines but the full range of Frescobaldi productions wines from six different estates across Tuscany, from the Chianti Classico zone to Bolgheri on the coast to the vineyards of Montalcino.

For those interested in the history as much as the wine, Castiglioni offers something few estates can match: a direct, physical connection to a thousand years of Florentine history. The family that financed the English crown, traded wine for Michelangelo’s paintings, and encouraged Dante to finish the Divine Comedy is still here, still farming the same hills, still making wine from the same land.

That history is not only in the countryside. In Florence itself, Palazzo Frescobaldi on Via di Santo Spirito has been in the family’s hands since the fifteenth century. It was the Frescobaldi who donated the land and resources that allowed the friars of Santo Spirito to build Brunelleschi’s basilica, the church whose bell tower and dome form the backdrop to the palace garden to this day. The palace was once connected to the church by a raised passage, so the family could attend Mass without stepping outside. For four years I had my office there, and the wine window the buchetta del vino, is still visible in the wall on the street. A small stone opening, worn smooth by centuries of hands passing coins and wine through it. The Frescobaldi story is not something you read about in a museum. In Florence, you can still touch it.

Some stories are worth tasting.

Interested in visiting Tenuta Castiglioni or other historic wine estates near Florence? Explore our private wine tours from Florence.