Lord Colliers Active Retirement Life

Monteriggioni to Siena

We left Monteriggioni on a cool, quiet morning. No coffee, no pastries—everyone seemed a bit off without the usual fuel—but the day ahead was short, and I was looking forward to Siena, a major milestone on the Via Francigena.

I said goodbye to the Italian ladies I’d been seeing along the way. The French pilgrims—who set off before me—are staying two nights in Siena, so this might be the last time our paths cross. Trail friendships are fleeting but meaningful.

The walk out of Monteriggioni was beautiful. Just before 7 AM, the sun was rising through the woods and the air was still cool. Birdsong followed me down gravel paths through vineyards and woods. I passed a few crumbling farmhouses and a new signpost with strange numbers—not marking the distance to Rome, so who knows what it meant.

This part of the Via Francigena feels different—warmer, more personal—than the early stages in France. The people, food, and landscapes all feel deeply Tuscan and deeply welcoming.

Along the way, I passed Castello della Chiocciola, a medieval watchtower known for its spiral staircase. Perched on a hill, it looks like something out of a fairytale. I didn’t go in, but just seeing it from the path was enough to spark the imagination.

Later, we stopped for a coffee at a small albergo and met a couple from Bristol who were finishing their walk to Siena and flying home that evening. They were well-traveled and full of great suggestions for walks along the South Coast of England and in the Scottish Highlands.

Approaching Siena, I entered through Porta Camollia and suddenly found myself surrounded by medieval stone buildings and narrow, winding streets. The city rises out of the hills like a fortress, and it feels like stepping back in time.

Siena itself is steeped in history. Once a powerful medieval city-state, it still holds that grandeur in its architecture and atmosphere. The Piazza del Campo is the heart of it all—broad, sloped, and full of life. The Duomo, with its striking black-and-white marble, is one of the most stunning cathedrals I’ve ever seen. I also stopped by Basilica of San Domenico, where relics of St. Catherine are kept, and admired the Torre del Mangia, which offers panoramic views of the surrounding countryside.

Siena feels like a living masterpiece, a place where time slows down and beauty takes center stage. What makes it even more special is the sense of anticipation it stirs—being here feels like an important step on the journey toward Rome. You can feel the momentum building, as if Siena is a checkpoint, preparing you for the grandeur that lies ahead.