The Via Francigena is an ancient religious pilgrimage route over three thousand kilometers long, starting from Canterbury, Great Britain, and crossing France, Switzerland and Italy, extending to Santa Maria di Leuca, the southernmost point of the “heel of the boot.” In the Middle Ages it was an essential route to reach Rome and the embarkation ports to the Holy Land. Today, although there are still faithful who travel it driven by religious motivations, it is an opportunity for a renewed relationship with nature and the territory.
Walkable on foot, by bicycle and on horseback, the Via Francigena extends in Tuscany for about 380 kilometers. After crossing the Cisa Pass and the important cities of Massa, Lucca and Siena, it enters Lazio near Radicofani. The long and varied Tuscan section crosses golden hills and millenary paths, touching some of the most beautiful and characteristic places in the region. Traveling the Via Francigena in Tuscany means immersing yourself in scenarios that seem to come out of a postcard.
Here we have selected the 5 most beautiful stages of the Via Francigena around Certaldo, all easily reachable from our holiday villa with pool in Chianti.
The stage, just under 30 kilometers long with a modest uphill elevation gain, begins from the Church of San Jacopo in Altopascio and ends at the Convent of San Francesco in San Miniato. In the initial part, at Galleno, you walk along a magnificent paved section of the ancient Via Francigena. You then cross the Cerbaie hills to head towards Ponte a Cappiano, where you can admire a beautiful bridge whose current form dates back to the first half of the 16th century, when Grand Duke Cosimo I de’ Medici decided to rebuild it. From here along the bank of the Usciana canal you cross an ancient swamp now reclaimed and climb towards the beautiful historic center of Fucecchio, characterized by a rich architectural heritage. After crossing the Arno, you quickly reach San Miniato, a charming village famous for white truffles and its history, represented by Frederick II’s Fortress and Matilde’s Tower.
From San Miniato begins a splendid but challenging stage that marks the passage from Pisan to Florentine territory. About 24 kilometers long, it ends at the Church of Cristo Re in Gambassi Terme. Having left the village of San Miniato, after an hour of walking on asphalt, you take an extraordinarily beautiful section along the hill ridges of Val d’Elsa, characterized by the presence of castles, fortresses, hospices and abbeys. Along the route you encounter two Submansiones: the Parish Church of Saints Peter and Paul in Coiano, a beautiful Romanesque style building made of sandstone and brick; and the Parish Church of Santa Maria Assunta in Chianni, which represents one of the greatest examples of late Romanesque architecture in Tuscany. The latter is located just a few minutes’ walk from the stage point in Gambassi Terme, a charming town that takes its name from its beneficial waters.
From Gambassi Terme begins a short transfer stage (just over 13 kilometers long), still interesting for the beauty of the panoramas that surround it. Nature is the protagonist until about halfway through the route, when you encounter the Sanctuary of Maria Santissima Madre della Divina Provvidenza in Pancole, inside which precious works of art are preserved. From the sanctuary you continue towards the characteristic hamlet of Collemucioli, with sections of ancient medieval paving, and then to the splendid Parish Church of Santa Maria Assunta in Cellole, considered one of the most important Romanesque parish churches dating back to the 12th century existing in the Val d’Elsa territory. The stage ends in Piazza della Cisterna in San Gimignano, a picturesque town famous for its soaring towers that earned it the nickname “Manhattan of the Middle Ages.”
This is one of the most evocative stages of the Via Francigena. It winds for over 30 kilometers through hills, knolls and groves that punctuate the most beautiful Tuscan countryside with biodiversity and rural landscapes. Having left San Gimignano, after an up-and-down section, you reach the vicinity of Molino d’Aiano. Continuing you intercept the beautiful town of Colle Val d’Elsa, known as the “Bohemia of Italy” for its long and renowned tradition in crystal production. Having departed from Colle Val d’Elsa you immerse yourself in the “Sentierelsa” river park, then reach the charming hamlet of Strove, with its beautiful Romanesque parish church, and the monumental complex of Abbadia a Isola. The stage ends in Piazza Roma in Monteriggioni, one of the most beautiful and famous medieval fortified villages in Italy. In the Middle Ages the supreme poet Dante Alighieri was so struck by it that he compared his vision to that of the giants placed in Hell.
The stage, about 18 kilometers long, is relatively easy. Having left Monteriggioni, you travel the white roads of the Montagnola Senese towards the ancient medieval village of Cerbaia. Then you continue in the woodland to the castles of Chiocciola and Villa, before descending into the reclaimed riverbed of Pian del Lago. Then you cross the Renai forest and reach Siena from Porta Camollia, one of the oldest Sienese gates. The stage ends in Piazza del Campo, one of the most beautiful squares in the world, famous for its shell shape as well as for being the place where the Palio di Siena takes place twice a year.
These five stages of the Via Francigena represent an extraordinary journey through the heart of Tuscany, where every step tells centuries of history, faith and tradition. From the medieval charm of San Gimignano to the fortified walls of Monteriggioni, up to the majestic Piazza del Campo in Siena, each stage offers unique emotions and unforgettable panoramas.
Staying in our villa with pool around Certaldo, you can easily reach these sections of the Via Francigena and live an authentic experience between spirituality and nature. Whether you are modern pilgrims or simply lovers of trekking and history, these ancient paths will give you moments of pure Tuscan magic, alternating walking with well-deserved relaxation in your holiday home.












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• The best rate guaranteed
• A bottle of Paluffo’s natural, organic red wine
• Honesty Bar with tea, coffee and still water (available 24/7)
• Private tour of the estate when you arrive
You’ll only receive these benefits if you book directly through our website.
