Private Day Trip to Val d'Orcia from Florence – Tuscany Hills

Val d'Orcia Private Tour: Montalcino, Pienza and Montepulciano

Rolling hills, Renaissance villages, and world-class wines — all from the comfort of a private vehicle.

This Val d'Orcia private tour from Florence takes you through one of Tuscany's most celebrated UNESCO-listed landscapes, visiting the hilltop towns of Montalcino, Pienza, and Montepulciano over a full ten-hour day. A dedicated chauffeur handles all logistics, allowing you to focus entirely on the scenery, architecture, and local wine.

The Val d'Orcia is a valley in southern Tuscany defined by its undulating terrain, cypress-lined roads, and a concentration of medieval and Renaissance settlements that have remained largely unchanged for centuries. Travelling between these towns by private vehicle means you experience the countryside as it was meant to be seen — slowly, and without the constraints of group schedules.

Each stop offers something distinct: Montalcino is the heartland of Brunello di Montalcino, one of Italy's most prestigious red wines; Pienza was redesigned in the fifteenth century as a model Renaissance city; and Montepulciano crowns its hilltop with noble palaces, imposing churches, and cellars producing the celebrated Vino Nobile.

Because the tour is entirely private, the pace is yours to set. Linger over a wine tasting in Montalcino, pause for photographs along a cypress-lined lane, or spend extra time exploring Pienza's cathedral square — the itinerary adapts to your interests throughout the day.