Where the Road Rises: Hill Towns from Villa Cetinale
Walking
Surrounding Villa Cetinale, the hills rise into a quiet rhythm of medieval towns - Monteriggioni, Volterra, Radda in Chianti, Colle Val d’Elsa. Each offers its own mix of stone streets, small piazzas, and panoramic views. Whether you come for a walk, a local market, or simply a slower afternoon, these towns invite you to linger rather than pass through.
Small in scale, but never in character - Tuscany’s hill towns offer their own sense of perspective. Monteriggioni appears like something drawn from memory: a perfect circle of walls, towers rising in even intervals, the stone weathered to a warm grey. Its piazza, framed by simple façades and a Romanesque church, is a natural place to stop. The rhythm here is slower. A short walk around the walls, a glass of Vernaccia, a plate of pecorino, and the day starts to take shape.
Volterra is different - higher, older, more complex. Known for alabaster and Etruscan origins, it holds a kind of quiet self-assurance. You come not for a list of things to see, but for its atmosphere: the way it opens gradually, through long views and narrow alleys. The food here feels rooted in place - earthy, local, well-matched to the surroundings.
Colle Val d’Elsa has a different tone again - a split-level town that feels half-finished and all the more interesting for it. Walk the upper town in the morning light, stop for lunch on the terrace below. In Radda, in the heart of Chianti, the wine lists read like maps and the views run uninterrupted for miles. Massa Marittima, slightly farther west, is worth the extra drive: an elegant hill town with a central piazza that feels almost too grand for its size - a cathedral, a fountain, and cafés spaced just enough apart.
You don’t need to choose one. These towns are close enough to see in pairs, to discover between meals, to return to without rush. From Villa Cetinale, the distances are short, but the sense of place is lasting.
DISTANCE FROM VILLA CETINALE
30 mins – 1 hr by car
WALKING DIFFICULTY
Low to moderate; hilly terrain but mostly paved
WALKABLE ROUTES
Monteriggioni, Volterra, Colle Val d’Elsa, Radda in Chianti, Massa Marittima, Monteriggioni to Colle Val d’Elsa via the Via Francigena.
For those curious to explore, the house manager at Villa Cetinale - can help shape the day. Whether it’s a scenic walking route between hilltowns, a table with a view, or the best time to visit when the crowds are few, she’s an invaluable guide to keeping things simple and well-paced.
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