Our itinerary in Chianti begins from the city of Florence, the starting point is the exit of Florence-Impruneta (old Firenze-Certosa) of the autostrada del sole (A1). The first stop is the town of San Casciano in Val di Pesa, along the way we can make a detour of several kilometers to visit the famous Albergaccio of Niccolò Machiavelli, in the village of Sant’Andrea in Percussina, known as the place where he lived Niccolò Machievalli, the author of “The Prince”.
San Casciano in Val di Pesa is a village that is located about ten kilometers from Florence, here are some things to visit, including the parish church of Santa Cecilia a Decimo, one of the oldest churches in the territory. The town of San Casciano preserves some parts of the walls and the keep, fortification works built by the Florentines in the second half of the fourteenth century. Among the most interesting churches of the town are: the Collegiate – rebuilt in the eighteenth century -, the church of Misericordia, and the church of Santa Maria del Gesù, where is the Museum of Sacred Art, which exhibits works of art from the surrounding churches.
Nearby San Casciano near the castle of Bibbione and Bargino is an important Etruscan tomb, the so-called “Tomba dell’Arciere”, which is dated around the seventh century BC. In the municipal area are also the church of Santo Stefano in Campoli – of which we have historical evidences since the tenth century – and the Castello di Gabbiano dating from the fifteenth century and which has the distinction of having the cylindrical towers on the sides.
Continuing along the Via Cassia we find first a large industrial area along the river Pesa and then the road begins to rise and to penetrate into the typical landscape of the Chianti, it runs along the castle of Poggio Petroio and the village of Romita, until reaching the village of Tavarnelle Val di Pesa. Just outside of town is the parish church of San Pietro in Bossolo which houses the local Museum of Sacred Art. The village was in the Middle Ages a stopping place for travelers and owes its name to the taverns along the way that welcomed travelers who traveled between Florence and Siena. The village today is modern in appearance, but at the highest point of the town is the old Franciscan church of Saint Lucia al Borghetto, a Gothic-style building built in the thirteenth century.
Along the road from Tavarnelle Val di Pesa to San Donato in Poggio, in the village of Morrocco, is the Carmelite convent of Santa Maria del Carmine, built in the fifteenth century, is now home to a community of Australian nuns. Continuing for a few kilometers you will reach the medieval village of San Donato in Poggio, still partly surrounded by walls and on which there are two gates. The heart of the village is the Piazza Malaspina overlook by the Renaissance Palazzo Malaspina, the Praetorian Palace and the Church of Santa Maria della Neve of the fifteenth century. A few hundred meters from the medieval center of San Donato in Poggio are the Pieve di San Donato in Poggio – a beautiful Romanesque church of the X century with a baptismal font in terracotta by Giovanni della Robbia -, and the late Renaissance Sanctuary of Santa Maria delle Grazie a Pietracupa.
On the road between Tavarnelle Val di Pesa and San Donato in Poggio a detour to do absolutely is the one that leads to beautiful Badia a Passignano, an abbey of the Vallombrosan order dating back to the eleventh century. Badia a Passignano has the appearance of a fortified village surrounded by the typical landscape of the Chianti region made of hills, vineyards and olive groves. Inside the abbey are an ancient library with manuscripts and old books, very nice is also the church of San Michele Arcangelo of the thirteenth century with frescoes in 1601 by Domenico Cresti said “Il Passignano”, while in the refectory of the monastery is the Last Supper fresco work of the fifteenth century of Domenico and Davide Ghirlandaio.
A little more than 2 km from Tavarnelle Val di Pesa is the medieval village of Barberino Val d’Elsa, still partly surrounded by ancient walls on which there are two gates, the most beautiful is the Porta Senese. Barberino Val d’Elsa is a balcony on the Chianti: from the medieval village, in particular from the facade of the church of San Bartolomeo, you can have a sweeping view of the Chianti, in front of the small village of Tignano, but the view stretches over most of Tuscany: the Apennines, the Pratomagno and the Monte Amiata. Inside the medieval village you will find some interesting buildings such as the Praetorian Palace with the facade full of coats of arms, the Palace of the Cardinal and the Pilgrim’s Hospital (Spedale dei Pellegrini). On the other side of the village in the gardens in front of the municipality and near the Porta Senese you have another beautiful view stretching from San Gimignano to the Apuan Alps.
There are numerous places to visit near Barberino Val d’Elsa, among the most interesting the Romanesque church of S. Appiano with inside some frescoes and the remains of the four pillars of the ancient baptistery in front of the façade. Here is also an Antiquarium collects Etruscan, Roman and medieval finds. Also fascinating is the small and partly abandoned village of Linari. The nearby village of Petrognano, immersed in beautiful landscape, is the place where until 1202 stood the castle of Semifonte, an important imperial outpost destroyed by the Florentines in 1202. Nearby is the famous dome of San Donnino built at the end of the sixteenth century it reproduces in 1:8 scale the dome of Florence Cathedral. Among the curiosities of the territory of Barberino Val d’Elsa the fortified village of Tignano, the Castle of Paneretta, and in the church of Santa Maria in the village of Marcialla with a fresco attributed to a young Michelangelo Buonarroti. Under Marcialla are the ruins of the Castle of Pogni of which remains a part of a tower.
Another interesting center of Chianti is the market town of Greve in Chianti, which arose as a market place in the center of an important agricultural area. At the center of the village is the triangular market square (Piazza Giovanni da Verrazzano) surrounded by arcades and at with an angle the parish church of Santa Croce. Greve is the birthplace of the explorer Giovanni da Verrazzano, who discovered the bay of New York, his statue is located in the market place dedicated to him. In the former convent of San Francesco is the local Museum of Sacred Art.
Around Greve are to visit the castles of Uzzano, Verrazzano, Lamole, Vicchiomaggio and Vignamaggio, the latter being the birthplace of Lisa Gherardini, the famous Mona Lisa by Leonardo. Among the medieval villages not to miss a visit to the pretty villages of Montefioralle and Panzano. Montefioralle is located above the village of Greve and is still surrounded by medieval walls. Panzano in Chianti is located along the road that connects Greve in Chianti to Castellina in Chianti, the Chiantigiana, there are the remains of the castle and a small medieval village, just outside the town of Panzano is the Church of San Leolino, a Romanesque parish church of the tenth century.
From Panzano we can go towards Castellina in Chianti and Radda in Chianti and continue the itinerary in the Sienese Chianti.