Rolling hills, cypress-lined roads, and a landscape so beautiful it became the definition of pastoral.
Tuscany is the landscape that taught the world what countryside should look like. The Val d’Orcia — a UNESCO World Heritage site south of Siena — rolls in waves of green and gold, punctuated by cypress trees, stone farmhouses, and hilltop towns that seem to float above the morning mist. It is almost absurdly beautiful, and it has been this way for centuries.
Siena is the great rival to Florence: a medieval city built around the shell-shaped Piazza del Campo, where the Palio horse race has been run since the 1600s. San Gimignano bristles with medieval towers on the skyline. Montepulciano and Montalcino produce two of Italy’s greatest wines — Vino Nobile and Brunello — and the tasting rooms here offer views as intoxicating as the vintages. Between the towns, the agriturismo tradition means you can sleep on working farms, eat food grown in the fields around you, and wake to a silence that cities have forgotten.
When to go: May through June for green hills and wildflowers. September through October for the grape harvest and golden light.
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