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Starting our itinerary in Chianti Fiorentino from the city of Florence, the starting point is the exit of Florence-Certosa of the autostrada del sole. From here take the highway Florence-Siena or the Via Cassia, following the Via Cassia, a detour of several kilometers, immediately after Tavarnuzze, well worth a visit the Albergaccio di Sant'Andrea in Percussina, famous for having welcomed within its walls the great political theorist Niccolò Machiavelli. The first place we come to is San Casciano Val di Pesa, now an attractive market and agricultural town. It originally grew up in this hilltop position close to the ancient parish church of Santa Cecilia a Decimo, already recorded in a document of 1043. The town still preserves traces of its ring of walls and a keep constructed by the Florentines in the second half of the fourteenth century to strengthen its role as a defensive outpost of the city of Florence In the upper section of the town stands the large Collegiata, rebuilt in the eighteenth century on the site of an earlier building. Before San Casciano, approaching from the north, Mercatale in Val di Pesa is the second largest town in the territory, while the surroundings feature numerous historic buildings of architectural interest. The municipal area boasts a rich artistic heritage. Several works originating from the local churches are now on display in the Museo di Arte Sacra, housed in the church of Santa Maria del Gesu, while other precious works are gathered in the church of the Misericordia (or of Santa Maria al Prato): among these are a beautiful marble pulpit by Giovanni di Balduccio and a crucifix attributed to the great Simone Martini. There are numerous castles and villa-farms in the surroundings: the Castello di Gabbiano, with round towers at the sides, or the castle of Bibbione of very ancient origins, nearby in 1978 was discovered a monumental Etruscan tomb, known as "Tomba dell'Arciere", which should go back to the third quarter of the seventh century BC.

Continuing southwards, we come to Tavarnelle Val di Pesa, which is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome. The territory of Tavamelle, like the entire Chianti district, has a particularly rich heritage of rural building: churches, oratories, chapels, villas and farms. In the town itself, of particular interest is the church of Santa Lucia al Borghetto, a rare example of local Gothic architecture. In the immediate vicinity, the interior of the Romanesque parish church of San Pietro in Bossolo contains interesting works of art. The Museo di Arte Sacra has been set up in the clergy house: among the paintings displayed, the most precious is a thirteenth-century panel portraying the Madonna and Child attributed to Meliore. Not far from Tavarnelle, in the Morrocco district, is the Carmelite convent of Santa Maria del Carmine, founded in 1481. Undoubtedly worth a visit is the mediaeval village of San Donato in Poggio. Overlooking the main square are the Renaissance Palazzo Malaspina and the church of Santa Maria della Neve. Not far from the village is the parish church of S. Donato where the interior houses a fine baptismal font in terracotta by Giovanni della Robbia. About a kilometre from the church stands the late Renaissance sanctuary of Santa Maria delle Grazie a Pietracupa, built close to a tabernacle which housed a Madonna believed to be miraculous. The most remarkable complex of the territory is the Badia a Passignano, founded by the monks of the Vallombrosan order in 1049. Set within a stupendous landscape, the Badia a Passignano appears like a fortified hamlet, dominated by a belltower and surrounded by constructions of different periods. The abbey possesses an exceptionally rich archive (almost seven thousand parchments) and precious works of art: the frescoes by Passignano in the church dedicated to San Michele Arcangelo and above all the Last Supper frescoed by Domenico and Davide Ghirlandaio in the refectory of the monastery.

To the south of Tavarnelle, set on a plateau boasting a magnificent panoramic view, stands the town of Barberino Val d'Elsa featuring numerous traces of its mediaeval past. These include extensive stretches of the walls, the entrance gates (that on the south side retains its original fourteenth-century features) and a number of buildings such as the Palazzo Pretorio, with a facade emblazoned with noble coats-of-arms, the Spedale dei Pellegrini (now the premises of the Council library) and the church of S. Bartolomeo rebuilt in neo-Romanesque style in the early twentieth century. Mandatory a stop to admire the landscape of Chianti that enjoys from the facade of the church in the historic centre of Barberino, from here in front you see all over the Chianti with in foreground the small fortified town of Tignano, dating back to the twelfth century.On the road to Petrognano-San Donnino, we reach the place where once stood Castle Semifonte, destroyed by the Florentines in 1202: to commemorate the event, in 1597 the octagonal chapel of San Michele Arcangelo was erected, to a design by Santi di Tito, crowned by a miniature version of the cupola designed by Brunelleschi for the Cathedral of Florence. Just a few kilometres away is the beautiful Romanesque church of San Appiano, a religious centre of enormous importance in the Middle Ages, named after the saint traditionally believed to be the first evangeliser of the Val d`Elsa. Particularly striking are the four cruciform pillars which stand in front of the church, part of the ancient baptistery which was later destroyed. Adjacent to the church is a small Antiquarium containing archaeological material which has come to light in the vicinity. A short distance from Sant'Appiano is the small village of Linari, partly abandoned. 

From Badia a Passignano we can head on towards Greve in Chianti. situated at what was the crossroads of an important road axis in past times. It developed predominantly as a market town, with a large market being held in the unusual triangular piazza lined with porticoes, which is still always busy and lively. The parish church of the town, dedicated to the Santa Croce, contains a triptych by Bicci di Lorenzo. The Museo di Arte Sacra has recently been opened in the former convent of San Francesco; it houses an important collection of paintings, sculptures, vestments and liturgical furnishings, a tangible sign of the artistic vitality of the local district. Greve is surrounded by delightful villages, such as Montefioralle with its stone houses and paved streets, or Panzano not far from which is the fine Romanesque church of San Leolino, with a five-arch sixteenth-century portico. The interior houses precious works of art. There are also many castles in the surroundings of Greve; originally defensive bastions they are now elegant residences or famous estates: Lizzano, Verrazzano (the name here recalls the famous navigator Giovanni da Verrazzano), Vicchiomaggio, Vignamaggio (where Leonardos famous Mona Lisa was born), and Lamole, to name but a few. Of considerable interest in terms of landscape is the Monte San Michele, the highest peak in Chianti (892 m).

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