Your 1-day Vespa loop from Siena itinerary [Chianti, San Gimignano, Certaldo…]

Text: Claire Lessiau
Photographs: Marcella van Alphen

While Siena slowly wakes up, we exit passing its medieval Porta Romana and leave the walled city for a day in the Tuscan countryside, each proudly riding a Vespa scooter. In Siena, do as the Sienese do… It is easy to understand why Italians love these scooters so much. They give a great freedom, allowing to take any kind of roads, from city centres to dirt tracks and to park easily (when it is becoming a challenge to drive a car, let alone park in and around Italian cities and even villages).

This carefully researched itinerary will have you discover the most iconic medieval villages in the north-eastern part of Siena through a part of the Chianti wine region. It can be done in a day, and may even be enjoyed better over 2 days.

1. Monteriggioni: the village of the fortified towers

The first stop is in Monteriggioni, a medieval walled village built on a hill by the Sienese people in the thirteenth century as a defence against the powerful Florence. Its imposing 10-meter high exterior walls with fourteen squared towers, visible from far away were taken only once despite the many clashes between the rival cities of Siena and Florence over the centuries. It was taken and its castle bombarded in 1553 when the Florentine troops were fighting along the imperial army.

Monteriggioni was a major stop along the Via Francigena and the name of one of the gates hints at this history: Porta Franca. On the main square, Piazza Roma, the calming chanting of monks attracts us to the Church of Santa Maria Assunta in Romanesque and Gothic styles.

2. Colle di Val d’Elsa: its unexpected hike by swimming holes

We continue our ride, past the hamlet of Strove, through beds of sunflowers along the winding road. We enjoy the smells of fig trees, and feel the warm wind on our skins. We soon arrive in Colle di Val d’Elsa. Named after the Elsa River, the calm village dominates the valley. An easy hike along the emerald green to turquoise blue waters of the stream is extremely enjoyable and offers opportunities to swim.

3. San Gimignano: where the red gold shaped world’s most famous medieval skyline

The quiet road winds through Tuscan landscapes between Colle di Val d’Elsa and San Gimignano, famous for its medieval skyline and one of the many UNESCO World Heritage sites in Tuscany. The 13 remaining fortified towers built between the 11th and 13th centuries within the ramparts of San Gimignano up on a hill are visible from quite a distance. The tallest one, the civic Torre Grossa, dominates the village with its 54 meters. Today, saffron is still cultivated on the surrounding hills of the famous hamlet. Brought back from the first crusade, the purple crocus with its bright red stigma was cultivated in San Gimignano and exported all over Europe. The red gold of San Gimignano built the wealth of the local families who built the towers. Penetrating the medieval town with its intact urban layout is still magical, despite the many day tourists from Florence. It is somewhat thanks to the Florentine power that San Gimignano has turned into an open-air museum: starting in 1353, waves of famine and plague forced the city into decline and under the control of Florence and preventing its Renaissance urban renewal.

4. Volterra: the off-the-beaten path ancient Etruscan, Roman and medieval town

The off-the-beaten path city is perched on its hill, 500 meters (1,500 feet) above sea level. It is fortified by its rampart, of which the oldest parts date back to Etruscan times (7th century BC) when it was one of the major cities trading alabaster and salt with the Greeks. The Roman conquest left traces that are still visible today such as the Roman Theatre (end of 1st century) and baths. Today, Piazza del Priori surrounded by its imposing 13th century palaces, showcases the power of the town during these times, before it declined towards the end of the Middle Ages. Like almost every Tuscan city, Volterra became a vassal of Florence in 1472. The Medici have built a fortress to tame the revolts and secure their control over the local alum mines. It has been a prison since the Renaissance.

5. San Vivaldo: the Jerusalem of Tuscany

San Vivaldo is a surprising place. It all started in 1325 when a chapel was erected where Saint Vivaldo had died. Over the years, it developed and the Franciscans built a Sacro Monti: between 1500 and 1516, 25 chapels were built to reproduce the Holy Land. With the fall of Constantinople in 1459, the Franciscans who organized pilgrimages to Jerusalem needed an alternative as the trip had just become a lot more complicated, dangerous and expensive. Places like San Vivaldo allowed believers to go on a local pilgrimage to the “Jerusalem of Tuscany” and venerate God. San Vivaldo was so special that Pope Leo X granted indulgences to its pilgrims. Indeed, its topography truly mimics the locations of the scenes of the New Testament. Brother Thomas of Florence who was the initiator of the project used the experience he acquired during his many travels to the Holy Land. Based on the orientation of Jerusalem, a wooden valley East of the Monastery represented the Valley of Josaphat; a small hill South of it, the Mount of Olives; a flat area North of it, the location of the Temple; and a small hill, the Calvary. There are 15 chapels remaining and each contains a statuary group in terra-cotta representing the life and passion of the Christ. The lady of pain is particularly expressive and the artisans were clearly following the Giovanni della Robbia’s school.

6. Certaldo

Certaldo also developed thanks to its proximity to Via Francigena that pilgrims used to walk from France to Rome. The high town is a very cute village perched on the hilltop built around its main street, Via Boccaccia that starts with the Pretorio Palace. The 12th century building is recognizable by its ceramics coat of arms on its facade, most of which by della Robbia family, the Florentine master craftsmen. As the coat of arm with six spheres hints at it, Certaldo was under the control of de’ Medici family. The atmospheric village with sweeping views on the surrounding Tuscan hills is the perfect stop for an aperitivo!

7. Castellina in Chianti

The last stop before looping back in Siena is Castellina in Chianti. The roads winds pretty steeply through a pine forest before reaching the village. It is considered by many as the capital of Chianti as this is where the consortium of the Chianti Classico was created in 1924 to defend the local wine. However, the origins of Chianti wines are much older and the first mentions date back to the 13th century. Cosimo III de’ Medici, who might have enjoyed its tiramisu with a glass of Chianti, defined the first wine region boundaries of the Chianti area in 1716. Since then, the Italian protected appellation (DOP) defined the grape mix for Chianti and the famous fiasco bottle in a straw basket has gained a solid reputation also thanks to the Super Tuscan wines for which daring local wine producers have innovated stepping away from the set rules. It is well worth stopping in a local enoteca (wine bar) to taste a glass of wine (moderately of course, as the Vespa needs to be driven back to Siena!).

Travel tips:

  • Go to SienaRent for well-maintained good quality scooters.
  • Check with San Vivaldo to go on a tour (otherwise the chapels are closed).
  • Check out this interactive map for the specific details to help you plan your trip and more articles and photos (zoom out) about the area! Here is a short tutorial to download it.

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9 thoughts on “Your 1-day Vespa loop from Siena itinerary [Chianti, San Gimignano, Certaldo…]

  1. This is an region of Italy I haven’t been to. While I wouldn’t do it on a Vespa, your post certainly gives me itinerary ideas. And your photos add to the inspiration. Thank you for sharing.

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