Two of Tuscany’s most atmospheric hill towns sit just half an hour apart, and both are within easy reach of Casole d’Elsa — San Gimignano, famous for its medieval towers, and Volterra, older and higher, built on Etruscan foundations. Together they make a gentle, cultural day that suits mixed groups and families.

San Gimignano: the medieval Manhattan

San Gimignano’s skyline of stone towers is unmistakable, and it is barely thirty minutes from my door. Get there before the coaches and you can walk the town while it is still calm. It is also the home of Vernaccia di San Gimignano, Tuscany’s noble white wine — worth a glass in a quiet enoteca before the crowds build.

Volterra: Etruscan and Roman

After lunch, Volterra feels like another world — higher, greyer, and far older. Its walls sit on Etruscan foundations, a Roman theatre lies below the town, and the alabaster workshops have been carving the local stone for centuries. It is quieter than San Gimignano and all the better for it.

An easy day, gentle on children

Because the two towns are so close, this is one of the least rushed days in the region — no long transfers, plenty of time to wander. It pairs a wine town with a history town without either feeling like a whistle-stop. See the San Gimignano & Volterra day.

Two walled towns, a glass of Vernaccia, a Roman theatre and an alabaster workshop — and never more than half an hour in the car.

When to go

Spring and autumn are ideal. In summer, aim to be in San Gimignano early and Volterra in the cooler afternoon. For more nearby ideas, see things to do near Casole d’Elsa.

Plan your day

Send me your dates and group size and I’ll set the pace to suit you — including extra time for wine or for the workshops. Quoted on request — one price for the whole van.