Tuscan Horizons: From San Gimignano to Siena

A journey through history, Tuscan landscapes, and dreamy villages. This section of the Via Francigena, connecting San Gimignano to Siena, is among the most fascinating of the entire route. It is designed for those who wish to savor every kilometer with calm and wonder: we have enriched the path with scenic variants and shorter stages, alternating with comfortable transfers, to offer you maximum pleasure — without haste.
It begins in San Gimignano, with its famous towers soaring above the hills like an ancient mirage. From here, the path winds through a succession of vineyards, stone farmhouses, cypresses, and rolling hills. The journey continues along river parks, country paths, and timeless small villages until reaching Monteriggioni, a perfectly preserved fortified castle that looks like something out of a fairy tale.
The arrival in Siena, with its unmistakable Piazza del Campo, is an emotional milestone. Among the city's districts (contrade), where the Palio is held every year, you will find the ideal place to celebrate the end of this unforgettable journey.
⏳ Recommended Duration: 2 days; 1 night
🚴‍♂️ Distance: 51 km
Tuscan Horizons: From San Gimignano to Siena

Da San Gimignano a Siena

1
An epic finale toward Siena – 51 km of history, nature, and pure beauty. The final stage of the journey is a crescendo of emotions: an itinerary that combines timeless villages, picture-perfect landscapes, and silent spirituality. Leaving the San Gimignano skyline behind, the path winds through harmonious hills and golden fields until reaching Colle Val d’Elsa, a village where time seems to have stood still. Its stone walls, narrow alleys, and the quiet of the historic center welcome you like an embrace.
From here, you enter one of the most intense stretches of the Via Francigena. Stop at the Pieve di Strove, a small church that invites contemplation, before reaching Abbadia a Isola, an ancient monastic complex that seems to merge with the landscape. Then, like a dream, Monteriggioni appears on the horizon: a perfect circle of walls dominating the Tuscan countryside. Climb the ramparts to enjoy a view that rewards every kilometer traveled.
The final stretch accompanies you to Siena, where entering through Porta Camollia marks the triumph of your journey. Now you can lose yourself in the charm of the contrade, sit in Piazza del Campo with a plate of pici all’aglione, and celebrate with a slice of panforte. It’s the perfect way to say: I made it. And every pedal stroke was worth it.

Siena

2
An extra day to experience Siena through art, flavors, and relaxation. After your triumphant arrival in Piazza del Campo, our advice is simple: dedicate at least one extra day to Siena. After so many emotions and kilometers traveled, this city deserves to be discovered slowly, savoring every moment. Siena is not just the final destination; it is an open-air masterpiece that invites you to slow down.
You can wander through the historic alleys of the contrade, admire the exquisite details of the Cathedral (Duomo), or climb the Facciatone for a sweeping view from the city rooftops to the surrounding hills. Treat yourself to the pleasure of "piazza life": a glass of Chianti Classico at sunset, the authentic flavors of cinta senese, or a plate of pici cacio e pepe in a historic tavern. A platter of pecorino cheese and honey is the perfect companion for a moment of pure relaxation. Staying an extra day isn't just an addition to the schedule; it’s the best way to end your journey by recharging body and mind with the very best of Tuscany.
Cookies preferences
0