A one-day itinerary between San Gimignano and San Galgano, designed for those who want to discover two very different yet complementary sides of Tuscany: on one hand, the lively medieval charm of a village renowned worldwide; on the other, the timeless silence of one of Europe’s most evocative abbeys.
It’s a journey that alternates stone and sky, history and legend, rolling hills and places of meditation—perfect for those who love to travel unhurriedly and let themselves be surprised.

The day begins in San Gimignano, which can already be seen from afar with the unmistakable silhouette of its towers rising from the hills like stone sentinels.
Entering the village, you immediately feel as though you’ve stepped back in time. Strolling along Via San Giovanni and Via San Matteo, among artisan shops and historic buildings, you naturally arrive at the two symbolic squares of the town:
Piazza della Cisterna, elegant and harmonious, and Piazza del Duomo, more intimate and solemn. The visit to the Collegiata of Santa Maria Assunta is one of the most moving moments of the morning: the frescoes covering the walls tell biblical stories with colors and details that are surprisingly vivid.
Those who wish can climb the Torre Grossa to admire from above the mosaic of hills, vineyards, and white roads surrounding the village. Before leaving San Gimignano, a pause is a must: a glass of Vernaccia wine or an artisanal gelato enjoyed while strolling is the best way to savor the atmosphere of the place.
Lunch can be enjoyed without haste, choosing a trattoria in the historic center or just outside the walls. The cuisine is simple and authentic: handmade pasta, local cured meats, and traditional peasant dishes that tell the story of the land as much as its monuments.
In the early afternoon, you leave San Gimignano and head towards San Galgano, crossing a wilder and less touristy part of Tuscany. The landscape slowly changes: villages become sparse, hills grow wider, and the silence deepens.
Arriving at the Abbey of San Galgano is always a striking moment. The large Gothic church, roofless, opens to the sky, creating a continuous dialogue between architecture and nature. Here, time seems to stand still: you move slowly, watch the light filtering through the arches, and listen to the wind.
Just a few minutes’ walk away lies the Hermitage of Montesiepi, an intimate and spiritual place that houses the famous Sword in the Stone, a symbol of Saint Galgano’s renunciation of worldly life. The legend, combined with the atmosphere of the site, makes the visit particularly evocative.
