Monteriggioni, Certaldo Vinci: a journey in the Tuscan countryside between Middle Ages, poetry and nature

Monteriggioni, Certaldo Vinci: a journey in the Tuscan countryside between Middle Ages, poetry and nature

The Tuscan countryside offers many villages and castles, each one different and with a story to tell. You can find here a two days journey to discover three beautiful Tuscan villages, through towers, old buildings, legends and many historical figures who lived there.

Monteriggioni, jewel of the Florentine countryside, looks like a place where time has stopped. The medieval castle on the top of a hill, visited annually by nearly 100 thousand tourists, was the stronghold of Siena against the Florentine Republic. Impregnable, it guaranteed for 300 years the freedom of the Republic of Siena resisting all attacks. Only in 1554 the captain of the Monteriggioni army secretly agreed with the Florentines betraying his companions, in exchange for personal favors. Dante Alighieri in the Divine Comedy dedicates two tercets to Monteriggioni, writing “Monteriggioni is crowned with towers …”, praising the shape of the castle, which still looks like a crown because of its 14 towers.



The visit starts from the medieval gate, which leads onto the large square facing the Romanesque church, the museum of medieval arms and many restaurants serving typical products. People can walk on the walls it for about 600 meters, enjoying a breathtaking view of the Montagnola Senese. The arms museum houses reproductions of Middle Age and Renaissance weapons and armors, including those of the Templars, who defended pilgrims going to Rome through the Via Francigena. The doors on the walls are only two – because they caused weakness – Porta Romea, looking towards Siena, and the S. Giovanni, looking towards Florence.
In the valley at the foot of Monteriggioni, there is an isolated tower, called the “fifteenth tower“. Its story is unusual: in 1000, the area that separated Monteriggioni from Abbadia Isola, an abbey under the control of the Bishop of Volterra, was covered with water. Volterra wanted to reclaim the area, while Siena wanted to keep the swamp, as a protection. In 1246 they came to an agreement: one part was reclaimed, while the water remained close to the castle. The tower was so used to control the water level.


Medieval feast Monteriggioni [Photo credits Kinzica Sorrenti]

Every year around the end of July in Monteriggioni there is a medieval festival, called “Monteriggioni is crowned with towers”. Residents dress up with antique clothes, soldiers guard the entrance doors, and you can meet jugglers, monks, merchants, and many other characters. A really impressive step back in time!

Certaldo Alta
At 30-minute drive, set among vineyards, cypress and olive trees and surrounded by the picturesque villages of the Val D’Elsa, stands one of the most charming and historical villages of the area, Certaldo Alta. The upper part of the city of Certaldo in fact is set on a hill, dominated by a castle, and offers of a maze of narrow streets that cross the small historic center, a real urban jewel. Here was born and spent his youth Giovanni Boccaccio, the famous author of the Decameron and poet of the ‘300.


Certaldo [Photo credits dvdbramhall]

Its name comes from Etruscans and Romans, who named it “cerrus altus”, that means “hill covered with oaks”. Under the dominion of Medici it was annexed to the Republic of Florence and was the seat of the Vicariate: on the Praetorian Palace facade, situated at the highest point of the village, you can still see all the coats of arms of the vicars who succeeded here, including those made of terracotta coming from Della Robbia workshop.
The visit of Certaldo Alta begins with the “climb” required to reach the village, located on the top of the hill. Who wants can reach the top of the hill walking through one of the three streets, Costa Alberti, Costa Vecchia or Via del Castello, while those who prefer a more comfortable ascent may use the funicular, which starts from Piazza Boccaccio.
Once on the top of the hill, you can start the visit walking the main street of the village, called Boccaccio street. You’ll immediately notice the medieval structure of the village, characterized by the path of the walls and many intact historical buildings. An entire block is occupied by the fourteenth century “Strozzi-Ridolfi” block, a building with two towers and an inner courtyard with an open gallery. Other attractions are Palazzo Machiavelli, and the Church of SS James and Philip, of Romanesque architecture, which houses the museum of sacred art and the remains of Giulia della Rena and of Boccaccio. Boccaccio’s house, rebuilt after the ravages of World War II, it is worth a visit. Then, the Praetorian Palace, next to which stands the church of St. Thomas and Prospero, the oldest of the castle, home of the “Tabernacle of executed” by Gozzoli. The doors and walls offer a unique panorama of the valley. A curiosity: the coat of arms of Certaldo until the twelfth century was the onion, refused only from 1633 to 1867, a period in which people of Certaldo, ashamed of it, replaced it with a rampant lion. They then return to the original coat of arms.


Mercantia 2012 – Boccaccio street – [Photo credits Gabriella Affini]

Do not miss the medieval festival “Mercantia“, which is held in Certaldo Alta every summer for five days in July. A real street theater with acrobats, jugglers, set, fire eaters, musicians, performances of all type, lights, light installations and much more.

A 40 minutes-drive gets to Vinci, birthplace of the famous Leonardo, where you can follow the artist and scientist’s footsteps.
Located between the southern part of Montalbano and Empoli, Leonardo spent his childhood in Vinci, before he was taken by his father to Florence. In the city, the Leonardo Museum collects machines, tools, gadgets and models accompanied by digital animations. Another piece of the artist’s history can be discovered in another Leonardo da Vinci museum, set in the basement of the Castle of the Counts Guidi, containing paintings of Leonardo’s workshop and an open-air section. Yet, the Santa Croce church, of Romanesque architecture, where Leonardo was baptized. There are also many works of modern art that the city has dedicated to him.

Leonardo Museum - Vinci

Leonardo Museum – Vinci

To the north of Vinci, in Anchiano, you can visit the birthplace home of Leonardo, located in a picturesque hilly landscape, which hosts a permanent exhibition. Here, you can discover the most intimate aspects of this genius, born in 1452, and the deep connection he had with his territory.

What to eat
You cannot leave the Tuscan countryside without experimenting some local dishes from Siena and Val D’Elsa, accompanied by an excellent local wine.
As a starter, croutons with chicken liver and with garlic and tomato: they are all prepared with Tuscan bread without salt, roasted and seasoned with local olive oil. Accompanying croutons, a platter of cold cuts and cheeses. As first courses, there’s plenty of choice: pappardelle with hare, ribollita – a soup made with bread, vegetables, cabbage, cheese and pepper – and pici, a type of fresh pasta, with meat sauce. In Certaldo, you should taste the onion, as soup or on croutons. Between second dishes, the pork loin, cooked with sage, rosemary and garlic, the Florentine steak – or sliced beef with rocket and parmesan – all coming from Chianina cows, or the famous Cinta Senese, accompanied by potatoes or beans with sage roast.

Florentine steak

Florentine steak

Among the desserts, “Ricciarelli”, almond cookies, “Castagnaccio”, thin cake made with chestnut flour, raisins and nuts, “Brigidini”, crispy bisquits with anise, or “Pane coi’ santi”, a sweet leavened bread, made with walnuts and raisins and pepper, prepared in Halloween period.
To accompany the meal, a nice “Chianti of the Siena hills”, intense and full-bodied, a “Vernaccia di San Gimignano” and Vin Santo as dessert, strictly accompanied by “Cantuccini”, almond biscuits produced in the area.

Where to sleep for a weekend in the Tuscan countryside?