Day 60 IT

San Gimignano to Monteriggioni

Can’t stop thinking about last night’s meal! We dined with the three Italian ladies we’ve come to know along the trail and were joined by a young Italian cyclist making the incredible journey from Canterbury to Rome. The camaraderie was amazing—plenty of laughter, shared stories, and deep conversations. It left a real impression on me. We finished the night with generous pours of red wine, a velvety Chianti that seemed to embody the Tuscan landscape itself—rich, smooth, and full of life. A round of grappa followed, the fiery Italian digestivo that gave the evening a fittingly warm and spirited close.

I have to say, the place we stayed last night had the best atmosphere of the entire trip so far. It reminded me of how meaningful these connections can be when you’re far from home but united by purpose.

A simple but satisfying breakfast started the day—before heading out around 6:15 AM.

The early mist clinging to the Tuscan hills made for a surreal and almost cinematic departure. The views from the village were nothing short of spectacular—arguably the best we’ve had so far in Italy. It was an energizing start to what would be a long day on foot, covering about 22 miles. With several more long days ahead, we’re beginning to feel the gravity and rhythm of the pilgrimage. Just two more days to Siena—a big milestone.

Each morning I think, this must be the best view yet, and then somehow the next day tops it. Today was no exception.
As we inch closer to Rome, we’re seeing more and more signposts pointing the way. There’s something incredibly encouraging about physically seeing the distance close in.

Today’s hike was a true feast for the senses. We wound our way through sun-dappled olive groves, the dusty paths occasionally giving way to panoramic sweeping views of the Tuscan countryside. The landscape is timeless—cypress trees, golden fields, and remote farmhouses perched on hilltops.

We passed through the charming village of Colle di Val d’Elsa, a peaceful stop with cobbled streets and a slower pace. Just before reaching Colle, we crossed a river with water so turquoise and clear, it looked like it belonged in a postcard. I’m not sure what minerals (limestone??) are responsible for that stunning color, but it stopped us in our tracks.

Arriving in Monteriggioni felt like stepping into a living painting. A walled medieval town perched on a hill, its towers still intact, seemingly untouched by time. From a distance, it rises dramatically from the surrounding landscape with no visible roads, as if floating above the modern world. It’s an epic and surreal sight.

Walking through the gate into the town was like being transported back into the 13th century. The silence, the stone, the history—it’s all very tangible.

Monteriggioni is tiny, but what it lacks in size, it makes up for in atmosphere. You can’t help but imagine what it must have been like centuries ago when knights walked these walls.

In the evening, we sat at a rustic café in the town square and sipped on a glass of local red wine. It paired perfectly with the wild boar (yes I finally found some)! The wine here tells the story of the land, much like everything else—it’s full of character, depth, and history.

What a day. What a walk. What a gift this whole journey continues to be. The crew had a last picture together. What great people. In the morning we all head out at different times! Tomorrow, it’s Siena, and I must say, I’m really enjoying Italy. It’s truly a fantastic place.