Chianti and Valdelsa on the road

The Chianti is the region between the cities of Florence and Siena and it is the same geographical area of the famous wine production. The car is the better vehicle to visit the Chianti region, not because of distances that are short, but for the freedom that this vehicle allows. You can visit the picturesque villages rich in history and culture, admire the breathtaking landscapes or stop to enjoy one of the many typical Tuscan products, with a good glass of Chianti wine.

The Valdelsa is the valley situated at the border of Chianti and it is historically important because crossed by the international way of communication that connecting France to Rome, the “Via Francigena“.
The heart of the Elsa Valley is Certaldo, the country where Boccaccio, one of the greatest Italian poets of the fourteenth century, he was born and died. The Val d’Elsa is an excellent base for visiting Tuscany by car.


Montespertoli is set in the classic countryside of the Fiorentine Chianti. The town is only 25km from Florence and Siena, Pisa, Volterra and San Gimignano are all the same distance away.
Montespertoli, with its vineyards, cellars and the Chianti Festival, is one of the Tuscan wine capitals. Historically the wine, as well as the oil and bread, has always been one of its most important features and is well-known in the region.

The territory was has always been an important commercial town for trade between Florence and north Italy along the via Volterrana and via Francigena. Look out for castles in the villages of Lucardo, Botinaccio, Poppiano, Montefugoni and Sonnino and the Renaissance church of Sant’Andrea in Montespertoli.

Gently sloping hills, olives groves, vineyards and woodland make it an ideal zone for excursions on foot, bike or horseback. The events throughout the year are rooted in local farming tradition and celebrate the harvests and change of seasons.

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Certaldo is a town of Tuscany, Italy, in the province of Florence.
Heading southwest, it is 50 minutes by rail and 35 minutes by car from the city of Florence. Heading north, it is 25 minutes by rail from Siena.
The town as a whole is picturesque, surrounded by vineyards. The older section, known as Certaldo Alto, lies on a hill 426 feet above sea-level. From there, one can see the marvelous towers of San Gimignano in the distance.

Certaldo was the home of the family of Giovanni Boccaccio, who died and was buried here in 1375. His house, of red brick, like the other old houses here, was restored in 1823 and furnished with old furniture. A statue of him was erected in the main square in 1875.

The Palazzo Pretorio, or Vicariale, the residence of the Florentine governors, recently restored to its original condition, has a picturesque facade adorned with ceramic coats of arms, and in the interior are various frescoes dating from the 13th to the 16th century.

Certaldo hosts several festivals a year: the largest and most famous is Mercantia, a week-long party in Certaldo Alto. It involves numerous street performers from across Italy, Europe and even the Americas.

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Montaione lies on the top of a hill in the heart of the Tuscany countryside, surrounded by the typical landscape of Elsa Valley, characterised by Chianti vineyards, olive trees, rows of cypresses and extended woods.

Montaione, which ancient origins comes from the Etruscan-Romans settlements, it’s today a town with 3.500 inhabitants, and offer every kind of service useful for your holiday, from banks to supermarkets, postal offices and tourist information desk, bus service handicraft shops and typical restaurants.
Thanks to the strategic and geographic position in the heart of Tuscany, Montaione is in an average of only 50 Km far from the most important and famous cities of art like Florence, Siena, Pisa and Lucca, without consider that to get San Gimignano and Volterra by car are sufficient only 30 minutes of driving.

Gambassi Terme

Gambassi is located about 35 km southwest of Florence, stretching stretches as far as the borders of the province of Siena.
After many centuries of agricultural traditions and craftsmanship, Gambassi is now tending towards an image of natural tourism and the thermal springs: for this reason, in 1977 the city to change its name to Gambassi Terme (at first being just Gambassi).

The city was already known in medieval times for its glass production (still manufactured here), and for being the birthplace of Domenico Livi, the artisan who made some of the stained-glass windows of Florence cathedral in the 1450s.

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Tavarnelle Val di Pesa

The small town of Tavarnelle Val di Pesa has Roman origins, and is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome.
The present town has a quite recent urban aspect as a result of the union of the three medieval villages: Tavarnelle, Mocale and Borghetto. The territory of Tavernelle, like the entire Chianti district, has a particularly rich heritage of rural building: churches, oratories, chapels, villas and farms.

Barberino Val d’Elsa

Founded by the Florentines in a strategic position to resist the expansion of the Semifonte castle, Barberino Val d’Elsa (named the berberian tiger, which is still the town’s symbol) still preserves its medieval appearance with its fortified walls, tower-houses, the Pretorio Palace (14th century), the Pilgrim’s Hospital (16th century) and the church of S. Bartolomeo.
From Barberino Val d’Elsa, following the road to Certaldo, one arrives at the remains of the Semifonte castle which was destroyed by the Florentines in 1202 after a long siege. Not long after the end of the 1500’s the chapel of S. Michele Arcangelo was built, according to a project by Santi di Tito, to commemorate Semifonte. While going Certaldo the romanesque parish church of S. Appiano can be found: it is one of the oldest to be found in the Florentine countryside, and dates back around the 11th century.

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San Gimignano

San Gimignano is a small walled medieval hill town in Tuscany, Italy, about a 35-minute drive northwest of Siena or southwest of Florence. It is mainly famous for its medieval architecture, especially its towers, which may be seen from several miles outside the town.

It served as an important relay point for pilgrims travelling to or from Rome on the Via Francigena. The patrician families who controlled the town built around 72 tower-houses (some as high as 50 m) as symbols of their wealth and power. Although only 14 have survived, San Gimignano has retained its feudal atmosphere and appearance.
The town also has several masterpieces of 14th- and 15th-century Italian art.

The town also is known for the white wine, Vernaccia di San Gimignano, grown in the area.
San Gimignano is a UNESCO world heritage site for its architecture.

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Casole d’Elsa

Casole d’Elsa lies on top of a hill, in the country between Siena and Pisa. It’s a small town characterised mainly by its buildings of ancient brick, placed on the ridge of a hill which has a beautiful, panoramic view.
Originally was an etruscan settlement and then a domain of the bishop of Volterra, Casole passed in the first half of the 13th Century under the control of Siena, in spite of the various rebellions provoked by the Porrina family for all of the first half of the next century. The sienese repeatedly reinforced and brought up to date the fortifications because of its defensive position. Casole’s “terra” (as a centre of habitation enclosed by walls used to be called in medieval times) had an almost pear-like shape, extending south to north for 420 metres and of a maximum width of about 130 meters.
All around the confines ran the enclosing walls, a great part of which is still visible today particularly along the western side, through sometimes incorporated in the walls of the houses.
One of the most representative manifestations of the tradition of Casole d’Elsa is the Palio, which takes place every year on the second Sunday of July.

Colle Val d’Elsa

Colle di Val d’Elsa is a town located above the valley of the river Elsa on the route of the ancient Via Francigena, the mediaeval highway frequented by pilgrims and merchants travelling to Rome from Canterbury and elsewhere in northern Europe.

Since 1331, glass production, which evolved into lead-crystal production in the 20th century, has been one of the most typical features of the town, which over the centuries, for this reason, has been called the ‘Bohemia of Italy‘, and is now the Città del Cristallo (Home of Lead-Glass Crystal).
All this is promoted by the Cristallo di Colle di Val d’Elsa consortium, a body which represents all the firms working in the sector, which represent 95% of Italy’s entire output of lead crystal, and 14% of global production.

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A credit card for deposit (Visa or Master Card) and a valid driver’s licence are required to rent our cars. We can collect/deliver both at the Certaldo railway station and accommmodation facilities.

Additional services

It is possible to take or to return the rented car near the Certaldo railway station or the accommodation facilities.

Accommmodation facilities

Hotel Certaldo – Certaldo
Hotel Villa Tavolese – Certaldo
Hotel Palazzo Mannaioni – Montaione
Villa San Paolo – San Gimignano
La Fonte Apartments – San Gimignano