The Val d'Orcia, the timing and the hilltop towns worth the drive, with the villas that put you in the middle of it all.
May 2026 · 1 min read
Tuscany rewards those who slow down. The light softens in the late afternoon, the cypress avenues throw long shadows, and the hilltop towns empty of day visitors just as the evening passeggiata begins. Knowing when to arrive matters as much as knowing where.
The Val d'Orcia
South of Siena, the Val d'Orcia is the Tuscany of the imagination: wheat fields, lone farmhouses and the spa town of Bagno Vignoni, where the piazza is a steaming pool. Base yourself here and Pienza, Montalcino and Montepulciano are each a short, beautiful drive away.
Arrive at a hill town for dinner, not for lunch. The crowds leave with the heat.
A Rouchelli specialist
Chianti, for the first time
Further north, the Chianti hills trade drama for intimacy: smaller vineyards, family trattorie and roads that wind between stone villages. It is the easier introduction, and closer to Florence for a day among the galleries.
Wherever you land, keep one day entirely free. The best afternoons in Tuscany are the unplanned ones: a roadside enoteca, a long lunch that becomes dinner, a town you stop in only because the bell tower caught your eye.
More from this region: Discover Tuscany
