Siena & San Gimignano Day Trip from Florence

San Gimignano rises from the countryside like a vision from the Middle Ages, its skyline defined by soaring stone towers that once proclaimed the wealth and power of rival families. During your guided visit, you explore the compact historic centre on foot, discovering how these towers functioned as private residences and status symbols in a fiercely competitive society. Though only 13 of the original 72 towers remain, they offer a vivid insight into medieval social hierarchies and daily life.

As you stroll through the town’s winding streets and piazzas, you’ll encounter art studios, wine bars, and traditional shops that echo San Gimignano’s long-standing commercial traditions. Your guide reveals how the town prospered thanks to its strategic position on the Via Francigena and its production of saffron, mulberries, and the celebrated Vernaccia wine. Away from the crowds, quieter alleyways and hidden corners reveal the intimate scale and enduring charm of this extraordinary hilltop settlement.

At the heart of San Gimignano lies Piazza del Duomo, the town’s medieval religious and political centre. Here you visit the Collegiata, whose interior is adorned with striking fresco cycles from the 12th to 14th centuries. Among the highlights is Taddeo di Bartolo’s dramatic Last Judgement, a powerful vision of salvation and damnation, alongside works by Bartolo di Fredi and Ghirlandaio that bring biblical stories vividly to life.

Nearby, Piazza della Cisterna takes its name from the ancient well at its centre and retains its distinctive triangular shape, framed by some of the town’s oldest buildings. Your visit continues to the Rocca, the fortress overlooking San Gimignano. From the top, you enjoy sweeping views across terracotta rooftops and the rolling Tuscan countryside beyond. These panoramic vistas offer not only beautiful photo opportunities, but also a deeper appreciation of the town’s strategic position and its enduring relationship with the surrounding landscape.

Siena unfolds as one of Italy’s most harmonious medieval cities, shaped by centuries of wealth, rivalry, and civic ambition. Your private tour begins at the remarkable Piazza del Campo, widely regarded as one of Europe’s greatest medieval squares. Its elegant shell-shaped form is surrounded by noble palazzi and dominated by the Palazzo Pubblico and the soaring Torre del Mangia, symbols of Siena’s once-independent government.

Here, your guide brings the square to life, explaining its role as the centre of political authority, commerce, and public ceremony. Siena’s prosperity was built on banking, wool production, and its position along the Via Francigena, allowing the city to flourish as a major cultural and economic power in the 13th and early 14th centuries. As you explore the surrounding streets and alleyways, you gain a sense of Siena’s unique identity, shaped by strong local traditions, neighbourhood rivalries, and a deep pride in its medieval heritage.