Lord Colliers Active Retirement Life

Gambassi Terme to San Gimignano

I woke to the sound of light rain, lingering from overnight showers. The air felt incredibly fresh—a crisp, cool start to what turned out to be a short but scenic walk. Today’s destination: San Gimignano, the famed “Town of Fine Towers,” known for its remarkable skyline of medieval towers once built as symbols of wealth and power among rival families.

Unfortunately, the morning started with a bit of unease. I received an alert from my home security system—someone had been in the backyard last night. It was disturbing at first, but after some calls, I found out it was my kind friends checking in to ensure everything was okay. 

I’m deeply grateful for the friends and family back home (USA/UK) looking out for me. Without their support / encouragement, this journey wouldn’t be possible. Cheers!

This stretch of the Via Francigena is about 13 km (8 miles) and is considered an easy to moderate walk. It winds through picturesque farmland, olive groves, and vineyards. The route includes gentle hills, dirt paths, and some paved stretches. It’s one of the most scenic days so far—classic Tuscan countryside at its best. Wildflowers and birdsong accompany you as you crest each ridge with panoramic views.

On the trail, we kept bumping into familiar faces—fellow hikers and pilgrims on the same path. It’s comforting to see the same characters each day; we share stories, trade photos, and enjoy each other’s company. It reminds me of the camaraderie found on the Camino.

One standout today was a fellow named Max who owns a large B&B and is originally from Bath, England. He splits his time between Tuscany and Hong Kong. He spoke passionately about the lifestyle here—making his own wine, enjoying the peace of the hills. Hearing stories like his makes you reflect on how different paths can lead to such contentment.

The morning hike was stunning. Though the sky remained overcast, the rolling Tuscan hills, vineyards, and ancient cypress-lined roads were absolutely breathtaking. It was the kind of walk that lifts your spirits, especially after last night’s anxiety.

We passed countless wineries today, each offering something unique. The variety of grapes and winemaking styles here is incredible. It’s no surprise that this region is so renowned for its wine culture—Chianti, Vernaccia, and beyond.

Since today’s stage was relatively short, we arrived in San Gimignano around 11 a.m. Approaching San Gimignano, the sight of its towers rising in the distance is truly iconic.

San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany. It’s best known for its dozen surviving tower houses, which give it a distinctive skyline. In the 14th century, there were as many as 72 towers—symbols of wealth and power built by feuding noble families. Today, 14 remain, most notably the Torre Grossa, which you can climb for panoramic views of the town and surrounding countryside.

The town is also famous for its Vernaccia di San Gimignano, a crisp white wine with a history dating back to the Renaissance. Its historic center is a UNESCO World Heritage Site, with cobbled streets, well-preserved architecture, and a sense of timeless beauty.

After arriving, I explored the town, grabbed a bite to eat, and treated myself to gelato from one of the famous local Gelateria’s—truly the perfect way to integrate into a new town! 

Tonight, we stayed at a local hostel (seven of us) and had dinner together. It was lively evening with stories, laughter, and maybe a little wine. These shared moments make the journey so much richer. Great people!