San Casciano in Val di Pesa

San Casciano in Val di Pesa is the northernmost municipality in Chianti. Being only 17 Km from Florence, it was very strongly influenced by late renaissance Florentine culture. Its origins are very old: the land was inhabited already during Etruscan times, as witnessed by the archaeological excavations in Monteridolfi (Archer’s Tomb) and Valigondoli.
During Roman times it was the site of a post-station on the road to Florence, later on, the bishops of Florence granted the hamlet its first civil statute in 1241.
In 1356, with the construction of its ramparts and gateways, San Casciano was officially recognized as a town.

Particularly interesting is its museum, which since 2008 has added an archaeological and a primitive dwelling section to the original sacred arts exhibit. In nearby Sant’Andrea in Percussina, just north of the town, stands the house where Nicolò Machiavelli spent his years in exile from Florence between 1512 and 1520, the same building being now the seat of the Chianti Classico consortium. Located at 319 m a.s.l. , it hosts the church of S. Maria di Prato. The historian Giovanni Carocci considers this church “the richest religious building in Chianti as for works of art”. The municipality lies between the Greve and Pesa valleys, covering a surface of 107.98 square Km, and counts a population of 16200 people.
It is well known for its olive oil and wine production.

What to see there: the church of S. Maria al Prato, the Collegiate Church; the library; Niccolini Theatre, San Pancrazio parish church (Romanic, 3 nave, ended by two apses, it holds a wooden crucifix dating from the 17th century); Pieve Santo Stefano a Campoli (Romanic, 10th century); Pieve di Santa Cecilia a Decimo; Pieve di San Giovanni in Sugana (232 m a.s.l., dating from the 12th-13th century).

In the surrounding area: S. Cecilia a Decimo parish church; Vicchiomaggio; Vignamaggio; Uzzano and Montefioralle castles; the churches of Santo Stefano and S. Andrea a Luiano; Gabbiano castle (11th century); the American War Cemetery; Bibione castle (built before 1000 A.D. after the year 1500 it was owned by Machiavelli).

Museums and monuments: San Casciano Museum (housed in the Church and Convent of S. Maria del Gesù), it displays a religious arts section, an archaeological one, and another dedicated to primitive dwellings. For more information: tel. 055 8256385. Also, Machiavelli House in Sant’Andrea in Percussina (he found refuge there in 1512 to write the world-renowned “Il Principe”).

Traditional and cultural events: the Patron Saint celebration (San Cassiano, August 13th, featuring a joust, historical costume parade and fireworks); “Mercantico” and “Fiera dei Confetti” (an ancient market reconstruction, “Confetti” being a hard almond candy) in April; “Roses bread and wine” in May; “Wine under the stars”, in July.

How to get there: View a map with directions

Greve in Chianti

Located in the heart of Chianti, Greve is one of the three municipalities, along with Radda and Castellina, which formed the Chianti League, constituted by the Florentine Republic to sort out its contrasts with Siena. Its origins go back to the Etruscan people. It has always been a thriving marketplace, as proven by the characteristic triangular perimeter of its main square. Provincial capital town in Leopoldine times, it lies on the left bank of the Greve river and is a perfect starting spot to then visit the Florentine Chianti and the Elsa valley, using road 222, or “Strada Chiantigiana”, linking Florence to Siena.

Inside its walls developed an economy made to supply all the local needs, thus, the local fare is for the rich and poor alike, which we would now call “zero kilometer”. Typical gastronomy includes “budelline” (guts and offal), tripe, variously recycled bread, courtyard animals and local game.
Here, in 1485, Giovanni da Verrazzano, who discovered the bay of New York and the Hudson River in 1524, was born. To him is dedicated a bronze statue, in Piazza Matteotti, where a plaque commemorates another famous person: Monsignor Giovanni Battista dei Ciampoli da Greve. Poet, disciple of Galileo, he wrote the report on the scientist’s most famous and controversial work, “Legge dei Massimi Sistemi”.
At 236 m a.s.l., with a population of 13.590, it is an important center for wine production, seat of the Chianti Classico market fair. It also produces some of the finest olive oil and cured meats.

What to see there: Piazza Matteotti, with its porticoes, historical workshops and restaurants; the old Town Hall; the neoclassical Church of Santa Croce (built between 1833 and 1835 by Cambray Digny on the ruins of an ancient Medieval chapel), holding a Madonna and Saints by Maestro di Greve and a triptych by Bicci di Lorenzo; the former Convent of San Francis (15th century), now the Museum of Sacred Art.

In the surrounding area: San Cresci parish church and Montefioralle Castle, Verrazzano Castle, Montescalari Abbey, Cintoia Castle, Lucolena in Chianti, Mugnana Castle, Lamole, S. Eufrosino Oratory, San Pietro a Sillano parish church, San Miniato a Rubbiana church, San Cristofano a Strada, Vignamaggio, San Michele Abbey in Passignano.

Museums and monuments: The Sacred Arts Museum and its archive, in the former convent of Saint Francis (closed on Mondays, for information call: 055 8544685).

Traditional and cultural events: Verrazzano Day (April 17th), the Flower Fair (first May weekend), “Calici di stelle” (nightly wine-tasting, July 10th), the annual Wine Fair (first or second week of September), Rificolona Fair (September 7th).

How to get there: View a map with directions

Tavarnelle Val di Pesa

Tavarnelle Val di Pesa lies 49 Km from Siena and 28 Km from Florence, at a height of 379 m a.s.l.
An ancient town on the road from Florence to Siena and then Rome, its name was “Tabernulae”, owing to the quantity of small taverns found there, to shelter and feed the travelers. In the 12th century it came under the Florentine Republic, which, strangely enough, did not provide for any defensive walls; it’s very likely it was never considered to be of any strategic value. Nevertheless, its position always gave it an important role as a commercial hub. Proof of this is the Franciscan Convent of Borghetto, as this sort of compound was always built only on the busiest thoroughfares. Only on May 1st, 1893, did it become a municipality, after being detached from Barberino Val d’Elsa.

What to see there: the Sacred Arts Museum, in Santa Lucia al Borghetto, (dating from the 13th century, in the simple style typical of the Franciscan order). Inside there are traces of frescoes belonging to the 14th century Sienese school, and, by the main altar, an Annunciation, dated 1471, attributed to Neri di Bucci. Also, the church of San Michele a Passignano.

In the surrounding area: Marcialla, with the Church of S. Maria, Borgo S. Donato in Poggio and its abbey, the Sanctuary of Santa Maria delle Grazie in Pietracupa, Morrocco (with its Carmelitan convent of S. Maria in Carmine, 1481), the monastery of Badia a Passignano (founded by the Vallombrosan monks in 1049, it holds almost 700 ancient parchments and many works of art, among which are the frescoes coming from the church of San Michele Arcangelo, and a Last Supper by Domenico and Davide Ghirlandaio in its refectory).

Museums and monuments: The Sacred Arts Museum in the Rectory of San Pietro in Bossolo (tel.055 8050833); the Emilio Ferrari Museum of Peasant Culture (tel. 055 8050824), in S. Donato in Poggio, with the Tavernelle Permanent Exhibition of Embroidery.

Traditional and cultural events: the Patron Saint celebration of S. Lucia (December 13th), the Threshing Festival (3rd July Sunday), the Music Festival (live concerts, 2nd May Sunday), “Calici di stelle” (nightly wine-tasting, August 10th), Chianti d’autunno-between sacred and profane (November and December, in the towns of Chianti, ends the tourist season).

How to get there: View a map with directions

Barberino Val d’Elsa

Barberino Val d’Elsa stands on the border between the Chianti and the Elsa valley, 44 Km from Florence and 31 from Siena. Situated in the Chianti Classico DOCG production area, Barberino, at an altitude of 373 m a.s.l., population 3.864, 65 square Km, is a charming little town in the province of Florence, appreciated for its rich folklore and local legends. The Italian Touring Club granted it its Orange Flag of Quality in February 17th, 2003.
An Etruscan settlement at first, a Roman one later, it really developed after the 13th century, after the destruction of the city of Semifonte by the Florentines. Its historical center shows the typical spindle-shaped appearance, with the main street linking the two city gates, one to Siena, and the other to Florence. This layout is found in all the walled towns of the Elsa valley.
Coming from Tavernelle, the fortified village is clearly viewed; its medieval past is evident in its well-preserved ramparts and gates.

What to see there: the Praetorian Palace, the “Spedale dei Pellegrini” (from 1365, now the seat of the Municipal Library, the church of San Bartolomeo, 6 Km northwards (neoromantic, built in the early 20th century).

In the surrounding area: Vico d’Elsa; Semifonte; Poneta; Marcialla; Petrognano Castle (with the ruins of Semifonte), where the San Michele Arcangelo Chapel is located (erected in 1597 by Santi Tito, it is a 1:8 reproduction of the Brunelleschi dome in Florence); Linari (ancient commercial center on the Siena-Florence road); San Filippo; San Martino ai Colli; Cortine; Olena. In Tignano there is the Romanic Parish of Sant’Appiano (11th century, it preserves the remains of the Saint, who lived between the 4th and 5th centuries), with its associated antiquarium, holding Etruscan artifacts found in nearby tombs; in Monsanto, Castello della Paneretta. 2 Km from S. Donato in Poggio there’s the Botanical Garden of Chianti.

Museums and monuments: Sann’Appiano Parish Church, Castello della Paneretta, Palazzo Pretorio, the church of S. Bartolomeo.

Traditional and cultural events: the S. Bartolomeo Patron Saint celebration (August 24th), Tignano Festival.

How to get there: View a map with directions

Castellina in Chianti

Castellina in Chianti is located 45 at Km from Florence and at 24 Km from Siena. It stands at 578 m a.s.l. and has a population of 2.665 spread out over a surface of 99,45 square Km. Located in the Sienese Chianti, it overlooks the Elsa, Arbia and Pesa valleys. For a long period of time it was the main thoroughfare linking Florence to Siena. Widely known around the world, it is the place where the Chianti Classico Consortium was established. Its emblem is, in fact, the famed Black rooster.

Castellina is of remote Etruscan origin, on the way between maritime Etruria and the northern cities. There are many ruins proving the presence of settlements already since the 7th century B.C.
First, there is the hypogeum of Monte Calvario, on the road to Florence, the most important archaeological finding in all of Chianti. It consists of four underground vaults, each with a main chamber and associated lateral cells. A local farmer accidentally came upon it in 1507, but only in 1915 was it rediscovered and excavated. Further north, one can find the ancient walled acropolis. In the south there is Poggino, where five tombs from the 6th century B.C. have been found, undoubtedly proving its significance as an archaeological site. Castellina hosts the Chianti Archaeological Museum, located in the main town square, which we strongly recommend for a visit (for more information call 0577 742090). There are four halls, dedicated to the following themes: the shepherds, the princes, the settlements, and Monte Calvario.
The town’s historical importance does not limit itself to the Etruscan period; many battles were fought here between the great local powers of Florence and Siena, each trying to assert its control over the strategically important position between the northern and southern Etruscan cities.

During the 13th century, with the towns of Gaiole and Radda in Chianti, it was the head of the Chianti League. It is at present very well preserved, featuring the imposing fortress, excellent tourist farms and fine vineyards. The best way to see it is by reaching the town center by Via delle Volte. To visit the outskirts, the tourist office (tel. 0577 741392) rents bicycles and organizes guided tours to the wine farms as well.

What to see there: The town Fortress (15th century), Via delle Volte, Via Ferruccio, Monte Calvario hypogeum, the church of S Salvatore.

In the surrounding area: Fonterutoli with the church of San Miniato; San Leonino and the Romanic church of San Leonino in Corno; Sant’Agnese; Rencine; La Piazza; Pietrafitta; Tregole; S.Maria in Colle (also known as Badiola), 5 Km from Castellina; Monternano (with the ancient castle’s ruins).

Museums and monuments: the Bianciardi and Straccali palaces; the church of S. Salvatore.

Traditional and cultural events: the Patron Saint of S. Fausto celebration (third September Sunday), the Watermelon Festival (August 24th), the local market on Saturdays.

How to get there: View a map with directions

Radda in Chianti

Radda in Chianti is situated at 48 Km from Florence and 28 Km from Siena, at the center of the Sienese Chianti Classico region, at a height of 535 m a.s.l., on the watershed between the Pesa and Arbia rivers. With its 1.710 inhabitants, over a surface of 80,56 square Km, it is a small town well worth visiting, excelling in the production DOCG Chianti Classico. The first recorded traces of this Etruscan town date back to 800 B.C., and the first reference to Radda Castle appears in the 11th century. It most likely passed on to the Counts of Guidi, in the year 1200, along with other castles in the area.

One of the towns constituting, in 1384, the Chianti League (along with Castellina and Gaiole in Chianti), it still displays an elliptic Medieval layout. At the center stands the “Palazzo del Podestà” (about the year 1400), its front decorated by many coats of arms. Now the seat of the municipality, its loggia houses the fresco of the Madonna with Child, between the Saints John the Baptist and Christopher (15th century).
The late-gothic Franciscan monastery of Santa Maria al Prato, dating from the 15th century, is the seat of the Museum of Religious Art; inside, one can see works coming from church of Radda and Gaiole. The Romanic church of San Niccolò is also well worth visiting, over the main altar looms a wooden crucifix (14th century), while in the left transept a “Madonna del Rosario” can be admired. Noteworthy fact, from Radda one can take hot-air balloon tours of Chianti, by contacting Agenzia Chiantimania (0577 738979).

What to see there: Piazza Ferrucci; Palazzo del Podestà; the church of San Niccolò; the Franciscan monastery of S. Maria in Prato (inside, a Madonna with Child by Neri di Bicci, 1474); the Grand-Ducal Icehouse (on the outskirts of town, close to the municipal gardens); Borgo di Volpaia with its ancient castle (of significant strategic importance, due to its position on the border between Florence and Siena), and the Commenda of Sant’Eufrosino (dedicated to the oriental Saint Bishop said to have evangelized the Chianti).

In the surrounding area: the Romanic Parish Church of Santa Maria Novella; San Fedele a Paterno; Santa Maria in Colle (La Badiola); Badia a Montemuro; Colle Petroso; Lucarelli; Monterinaldi Castle; Palagio; Selvole; Volpaia; La Villa; Albola Castle. On the road between Castellina and Radda one can visit the archaeological site of Poggio la Croce. There, artifacts from the Bronze and Copper Ages, along with the ruins of buildings from pre-Villanovan times are on display.

Museums and monuments: Center for the Historical Studies of Chianti; the Sacred Art Museum.

Traditional and cultural events: the San Nicolò Saint Patron celebration (September 29th); Festa del Perdono (on the Monday following the last August Sunday, and the preceding Friday and Saturday); Festa della Croce (first August Sunday); Festival of San Lorenzo alla Volpaia (August 10th); the weekly market fair of Radda (the fourth Monday of every month). Live concerts at Lamole Castle; the Villa Festival of Swifts (mid-July); Radda in the wine-glass (first June weekend).

How to get there: View a map with directions

Gaiole in Chianti

Gaiole in Chianti stretches along the course of the Massellone stream, in the south of the Chianti. Its role as a meeting and marketplace is recorded since the first millenium A.D.
In the 14th century, with the contitution of the Chianti League, the town, along with Radda and Castellina, rose in status. Long situated on the border between Florence and Siena, it was bitterly fought over, until the victory of the former in 1555.
With an abundance of castles in the whereabouts, it is surrounded by woodlands, and in the southwards-facing hills, vineyards have for hundreds of years produced, and still do, high quality wines, Chianti Classico in particular. The town is situated at 25 Km from Siena, and 57 Km from Florence. It extends over 128,99 square kilometers, at 367 m a.s.l., and is home to 2.600 inhabitants. Its highlight is the Chianti Castles Route, comprising six itineraries designed to explore in detail the prestigious surroundings.

What to see there: the castle of Castagnoli; Spaltena Village; the parish curch of S. Maria; Vertine Village; the church of S. Pietro; Brolio Castle (built by the Longobards, the Ricasoli family settled there in 12th century); Montegrossi Castle (700 m a.s.l., it is known since 1007); Tornano Castle (it features one of the most impressive defensive structures in the area); Vertine Castle (owned by the Ricasoli family since the 13th century); Torre dei Cancelli (a massive, square watchtower, it controls the gap between the Arno valley and Chianti).

In the surrounding area: at two kilometers, the castle of Barbischio, at four, Meleto Castle (originally an abbey administered by the Vallombrosan monks in Coltibuono since the 11th century), at eight kilometers Brolio Castle, and at four, Coltibuono Abbey.

Museums and monuments: the parish church of S. Giusto in Salcio (12th century) and San Lorenzo in Coltibuono (11th-12th century).

Traditional and cultural events: the Patron Saint celebration of S. Sigismondo (July 17th).

How to get there: View a map with directions

Castelnuovo Berardenga

Castelnuovo Berardenga is the southernmost municipality in Chianti. It is at 57 km from Florence and 20 km from Siena, on a hill over the Ombrone and Malena rivers. It spreads over 177 square kilometers, stands at 350 m a.s.l. and has a population of 8.992.
The castle from which it takes its name (of which only a tower and a few ruins still stand), was erected in 1366 by the Republic of Siena, with the purpose of securing the area.

The distinctive feature of the small town is Villa Chigi Saracini, surrounded by its extensive park (open to the public). In the historic town center, the Clock Tower and the Neoclassical church of the Saints Giulio and Clemente (with a “Madonna with Child” by Giovanni di Paolo), are worth a visit.
Its economy is based on the vineyards, along with the production of cheeses and cured meats. Excellent wrought iron is also crafted there. At about 7 kilometers is Monteaperti, hometown of the painter and sculptor Domenico Beccafiumi (1486-1551).

What to see there: the town center; Villa Chigi Saracini; the parish church of Santa Maria Maddalena (in Pàcina); San Gusmé Castle; Villa Bianchi Bandinelli in Reggiano; Villa di Pagliaia.

In the surrounding area: Monteaperti; Aiola; Borgo Scopeto; Canonica Cerreto; Castell’in Villa; the chartreuse of Pontignano; Corsigano; Dievole; Félsina; Pieve Asciata; Quercegrossa; Selvose; S. Felice; S. Gusmé; Vagliagli; Villa Arceno; Cetamura.

Museums and monuments: the Landscape Museum (via Chianti, 59, tel./fax: 0577 352035). It delves on the relationship between Man and his surroundings, between reality and its perception. It consists in a thematic itinerary including various kinds of landscapes, chosen among the most significant in the province of Siena. Touring the halls, one passes from the territory’s natural characteristics to its role in history and science and then to its significance in cinema and advertising.
The visiting hours can be found on the Museum’s official Facebook page. We also would like to recommend the fascinating and mysterious Synagogue of Murlo, 14 kilometers from Asciano (closed on Mondays).

Traditional and cultural events: the celebration of the Patron Saints Giusto and Clemente (June 5th), and the weekly market fair (Thursdays).

How to get there: View a map with directions


Set amid green hills, on the banks of the Elsa River, Poggibonsi flourished as a commercial center during the Middle Age, mainly because of its position on the Via Francigena. It was founded around the end of the13th century, with the name of Podium Bonitii. Guido da Montefeltro destroyed its castle in 1270, during the war between Siena and Florence. Now it is a modern town and the major industrial center of the Elsa valley, producing, namely, recreational vehicles and furniture. The population is over 27.000, and its altitude is 116 m a.s.l. Among the most relevant sites, there are the Neoclassical Collegiate, the church of San Lorenzo, the Spring of the Fairies, and the modern “Doorway of Peace”, by Giuseppe Calonaci, in the church of San Giuseppe. Not to be missed, lastly, a stroll through the Vernaccia vineyards, as it is from those grapes that the Sienese Chianti is made.

What to see there: the Praetorian Palace, with its embattled gothic tower; the Santa Maria Assunta Collegiate (housing a “Resurrection” by F. Botticini and a baptismal font dated 1341); the Church of San Lorenzo; the Spring of the Fairies (13th century); the fortress of Poggio Imperiale (commissioned by Lorenzo il Magnifico, but never ultimated); the San Giovanni alla Magione hospital; the Convent of San Lucchese.

In the surrounding area: 7 Km to the south, Staggia, with its 14th century fortress, and S. Maria Assunta Parish Church. At 6 Km to the north, the church of San Pietro a Cedda, where olive oil, honey, and Vin Santo are produced.

Museums and monuments: the Gallery of Modern Art Via Maestra, 114 (in via della Repubblica, 114, tel. 0577 98352); the Archaeological-Technological- Environmental Park in Poggio Imperiale, there, one can admire the vestiges of Late-antique, Longobard, and Carolingian settlements; the Art Collection in Pieve di Staggia (Piazza Grazzini, 1, tel. 0577 930901), it holds a number of 14th century paintings and fragments of frescoes from the Santa Assunta Abbey, among which, one by Il Pollaiolo.

Traditional and cultural events: the San Lucchese Patron Saint celebration (April 28th); the festival of Santa Signora della Milizia; Calendimaggio; the Festival of Springtime, (in May); the Festival of San Michele (3rd week of September); the International Festival of Shadows (in Staggia, in June).

How to get there: View a map with directions