I’ll take you to discover the Val d’Elsa among medieval villages and postcard views of the Tuscan hills along the Via Francigena

There are places that seem to have come out of a painting, territories where every bend in the road offers rows of cypress trees, soft hills and stone villages suspended in time. My journey to Val d’Elsa began like this, crossing a Tuscany different from the chaotic one of the art cities, slower, quieter and incredibly authentic.

Between Florence and Siena, along the historical route of the Via Francigena, I discovered an area made up of medieval castles, artisan workshops, scenic squares and panoramas that seem to have been built specifically to stop and look at them. Each village had a precise identity: some guarded ancient towers, some the scent of truffles, some centuries-old traditions linked to crystal.

Certaldo, the red village of Boccaccio

The first stop was Certaldo, one of the villages that struck me most for its intimate and almost cinematic atmosphere. We left the camper in the lower part and went up towards Certaldo Alto, the medieval heart of the town, thanks to the funicular.

Here everything speaks of Giovanni Boccaccio. His house-museum dominates the village and tells of the deep bond between the writer and this corner of Tuscany. Walking along Via Boccaccio I had the feeling of being in a suspended dimension, far from the frenetic tourism of other more famous locations.

The Palazzo Pretorio is also beautiful, with its façade decorated with ancient coats of arms and the rooms that tell of centuries of Florentine history. But the real surprise was simply walking aimlessly within the walls, stopping to observe panoramic terraces, medieval arches and small taverns where you could taste the typical local dishes.

San Miniato, the kingdom of the white truffle

Of all the towns visited, San Miniato is the one that best combines medieval elegance and gastronomic tradition. Arriving from afar you immediately notice the profile of the village perched on the hill, dominated by the famous Rocca di Federico II. The climb towards the historic center offers spectacular views of the Tuscan countryside. Once at the top, the sensation is that of entering a noble, refined city, rich in history and surprising architectural details.

The Piazza del Duomo is one of the most beautiful corners of the village, but what makes San Miniato truly special is its link with the white truffle, the absolute protagonist of the local tradition. Everywhere you can breathe gastronomic culture: restaurants, shops and small trattorias offer simple but incredibly intense dishes. Climbing up to the Rocca tower was one of the most evocative experiences of the trip. From up there the view over the Val d’Elsa seems infinite.

Casole d’Elsa, the quietest village on the trip

If I had to choose the most relaxing place of the entire itinerary I would undoubtedly say Casole d’Elsa. It is less touristy than other Tuscan villages, but precisely for this reason it retains a genuine charm. Walking in the historic center I found an intimate Tuscany, made up of small squares, stone houses and open views of the Sienese hills.

The Rocca Senese dominates the village and tells the story of the medieval past of the town, while the Palazzo Pretorio still preserves perfectly visible coats of arms and historical details. We stopped for a long time near the panoramic terrace overlooking the countryside: one of those places where time seems to really slow down.

Colle di Val d’Elsa, the city of crystal

Before arriving there I only knew Colle di Val d’Elsa for its fame linked to crystal, but visiting it in person was a constant surprise. The upper part of the village, called Colle Alta, is a mix of medieval streets, historic buildings and spectacular panoramic points.

The tradition of artisanal crystal is perceived everywhere. In the shops you can still see handmade workmanship and objects that look like works of art. The Ponte del Campana is also beautiful, one of the most photographed corners of the village.

Monteriggioni, the perfect castle in Tuscany

The last stop of the journey was probably the most iconic: Monteriggioni. Seeing it appear among the hills is impressive. Its circular walls and medieval towers look like something straight out of a historical film. Entering the village through one of the ancient gates really gives the sensation of crossing a temporal border. Inside the walls everything is gathered around the main square, dominated by the Romanesque church and perfectly preserved historic buildings.

The walk along the wall walkways was one of the most beautiful moments of the entire trip. From up there you can observe vineyards, olive groves and the Sienese countryside which extends as far as the eye can see. Monteriggioni is small, but has an incredible scenic power. It is one of those places that remain imprinted in the memory much longer than one expects and it is not for nothing that it is one of the most scenic arrivals of the Via Francigena with many walkers who crowd it.

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