HistoryThe Via Chiantigiana, world-famous route between Florence and Siena, extends for approximately 70km/43mi through the Chianti district between the valleys of the Arno and the Ombrone.Virtually every town and village in Chianti celebrates its own festival in September or October.
Florence to Siena by the Via Chiantigiana
A visitor who is driving through the hilly Chianti district south of Florence should make a stop in Impruneta. This little town, with its population of about 15,000, is famous for its ceramic and pottery studios as well as its chemical and engineering works.
Santa Maria dell'Impruneta
The 11th century basilica of Santa Maria dell'Impruneta is in the center of Impruneta. Walls and towers were built around the building when it was renovated in the 14th and 15th centuries. It was badly damaged in the Second World War.Features worth seeing in the interior are two richly ornamented tabernacles by Michelozzo (1453-1456), resembling the church of Santissima Annunziata in Florence, the Cappella della Croce and the Cappella della Madonna, both containing work by Luca della Robbia.The sculptural silver altar front is of exceptional quality.
Some 4km/2.5mi or so before Greve two interesting medieval castles lie off the road to the right. The first, Castello Vicchiomaggio, sits encircled by cypresses on a hill with panoramic views. The oldest parts of the building, the tower and wall, date back to the 13th century. It is said that Leonardo da Vinci once stayed in the villa, now carefully restored - the castle certainly receives a mention in one of his works. Later the Médici held magnificent feasts here in spring.
Castello di Verrazzano
The Castello di Verrazzano bears the name of a family whose most famous son, Giovanni Verrazzano (1485-1528), was the first European to set eyes on what is now Manhattan Island (in 1524). The bridge between Brooklyn and Staten Island in New York - the longest suspension bridge in the world - is named after the explorer. Stones from the castle were even incorporated in the bridge during its construction. Proud cypresses and lovely flower beds adorn the castle gardens.
Castello di Uzzano
About 1.5km/1mi before the little town of Greve a detour can be made, to the east of the main road where a narrow country lane climbs steeply between olive groves to the medieval Castello di Uzzano (restaurant serving delicious Tuscan specialities). Converted to a villa by the Capponi family in the mid 16th century, in 1641 the elegant house became the property of the Counts Masetti. It was further enlarged in the 18th century. Today visitors are greeted by graceful arches embellishing a courtyard with a fine two-storyed arcade.
Greve (population 11,000) boasts an unusually attractive triangular piazza, the arcaded Piazza Matteoti, around which cluster several cozy trattorie and enoteche and the Antica Macelleria Falomi (No. 69) famous for its wild boar ham and fennel salami. The parish church of Santa Croce has a 15th century triptych by Bicci di Lorenzo and a Madonna by the so-called Master of Greve (13th century). A major festival, the week-long Rassegna del Chianti Classico, is held here in mid September.
Connoisseurs should not be deterred by the at times very steep 2km/1.25mile road to the neighboring village of Montefioralle where excellent olive oil is produced. The Chiesa San Stefano is the start of an agreeable circular tour of this charming medieval village, its marketplace ringed by shady, leaf-covered walks.
Badia a Passignano
Visible in the distance amidst tall cypresses is Badia a Passignano (6km/3.75mi west of Montefioralle), a Gothic monastery founded in 1049 by Saint John Giualberto who established the Vallombrosan Order of Benedictines. The refectory is graced by an exceptional "Last Supper" painted by Domenico Ghirlandaio in 1476.
Lamole & Villa Vignamaggio
Panzano in Chianti
Panzano, up to the right of the SS 222 (1km/.75mi; 498m/1,634ft), is an enchanting little spot, definitely not to be missed. Be sure also to visit the Romanesque Pieve di San Leolino, a short distance further on along the main road. Among its treasures is a 13th century triptych by the Master of Panzano.
Barberino Val d'Elsa
The little town of Barberino Val d'Elsa (373m/1,224ft; population 3,500) is some 20km/12.5mi west on the old Roman Via Cassia. Though outside the Chianti Classico district proper, it is surrounded by vine-covered slopes. Barberino remains encircled too by the walls which served to protect this small Florentine town during the conflict with Siena. Two impressive 14th century gate-towers, the Porta Romana and Porta Fiorentina, guard the openings through the circuit wall. At the end of the Via Francesco da Barberino stands the 14th century Ospedale dei Pellegrini (pilgrim hospice) erected by Cecco Barberino in 1365.
The Palazzo Pretorio in the Piazza Barberini - Barberino Val d'Elsa's main square - is adorned with numerous coats of arms, the oldest of which date from the 15th century. The nearby parish church of San Bartolomeo contains remnants of 14th/15th century frescoes (Annunciation).
Castellina in Chianti
Next stop on the Chiantigiana is Castellina in Chianti (population 3,000). Just outside this trim medieval village on the Florentine/Sienese border there is an Etruscan tumulus (Montecalvario, seventh century). Castellina itself is dominated by its early 15th century castle. The parish church boasts a fresco by Bicci di Lorenzo, also 15th century.
Radda in Chianti
From Castellina a country road makes its way to Radda (13km/8mi east) before skirting the southern slopes of the Chianti hills. Radda (533m/1,749ft), in the possession of the Counts Guidi from before the year 1000, passed in 1203 into the hands of the Florentine Republic and from 1415 was the headquarters of the Chianti League. Still encircled by its medieval walls, the pretty town center makes an inviting setting for a walk.
Radda - Palazzo del Podestà
At the very heart of Radda stands the 15th century Palazzo del Podestà, embellished with coats of arms and an imposing arcade. Its clock has chimed the hour since the Middle Ages. Just a short distance away a picturesque fountain adorns steps leading up to the parish church of San Nicolò which has a fine fresco on its façade. The vine-covered slopes around the town have the look of neat-hedged ornamental gardens.
Villa di Vistarenni
Situated about 5km/3mi outside Radda, the exotic-looking Villa di Vistarenni with its unusual decorative facade was built for the Strozzi family in the 16th/17th centuries. In 1988 its owner Elisabetta Tognana founded the Associazione Nazionale Le Donne del Vino, the Italian association which today has a membership of over 200 highly successful producers and sommelières.
Castello di Brolio
A few kilometers beyond Castello di Meleto a road branches off southeast towards Castello di Brolio (8km/5mi), an impressive sight in its elevated position on a 530m/1,739ft-high ridge. The history of this mighty fortress, the archetypal Chianti castle, is closely linked to that of the Ricasoli family, rulers of the region from the 13th century. As a strategic stronghold close to the Florentine/Sienese border, the castle was repeatedly engulfed in bitter fighting. Badly damaged on numerous occasions, the last being at the hands of the Sienese in 1529, it was extensively rebuilt in the 16th century. In about 1860 Bettino Ricasoli (1809-90) commissioned Pietro Marchetti to transform the fortress into the imposing red brick Neo-Gothic castle seen today. The great dining hall with its Flemish tapestries, suits of armor and family coats of arms is particularly noteworthy.
Gaiole in Chianti
Like Radda, Gaiole (13km/8mi; population 3,000) is a picturesque town. The Romanesque parish church of Santa Maria e Spaltenna dates from the first half of the 12th century. Today gourmet meals can be enjoyed in the stylish surroundings of the old cloister.
Badia a Coltibuono
Now converted into a splendid villa, the former single-aisled Badia a Coltibuono about 5km/3mi north of Gaiole is still a fine example of Romanesque architecture. Consecrated in 1049, in 1402 it was taken over by Benedictine monks from Vallombrosa who renovated the cloister and the residential and domestic buildings. Between 1810 and 1842 the by then secularized property was managed as an estate. (First-class restaurant and best quality olive oil.)
Castello di Meleto
Castello di Meleto, 4km/2.5mi south of Gaiole, was founded in the 11th century. In the 13th century the castle with its circular corner towers was turned by the Firidolfi family into one of the strongest fortresses in the Chianti League. Thereafter it withstood every siege to which it was subjected until 1498.
Castello di Volpaia
The castle in the little hamlet of Volpaia (population 150) 5km/3mi north of Radda is first mentioned in a document dating back to 1172. Its present owner Giovanella Stianti-Mascheroni is the daughter of the publisher. Every September the castle is turned into an art gallery with exhibitions of art.
A pyramid on the hill opposite the little village of Montaperti (8km/5mi south of Castello di Brolio) commemorates the decisive battle fought here in 1260 which gave Siena final victory over Florence.
The landscape of Chianti can again be seen at its very loveliest on the last stretch of the Chiantigiana proper between Forterutoli - a village first mentioned in a document of 998, with a charming townscape and pretty piazzetta well worth pausing to enjoy - and Quercegrossa. Interspersed between wooded hilltops and olive groves mingle in pleasing harmony while dark rows of cypresses mark ancient lanes to abandoned manor- and farmhouses. Then, at journey's end, the rust-red circle of houses that is Siena comes finally into view.