Pienza and Montepulciano by Tuscan Hills from Rome Private Tour

About this tour

A 10-hour private drive from Rome into the rolling hills of Val d'Orcia, visiting two handsome Tuscan hilltop towns. You'll spend time wandering Pienza's Renaissance streets and Montepulciano's medieval lanes, with tastings of local cheese and wine woven through the day. The landscape itself—vineyards, cypress-lined roads, stone farmhouses—is the real draw here. Your English-speaking driver handles all the navigation while you take in one of Italy's most photogenic corners.

Highlights

• Val d'Orcia UNESCO landscape, cypress avenues and rolling wheat fields
• Pienza: Renaissance piazza and travertine architecture
• Montepulciano: steep cobbled streets, Renaissance palaces
• Local cheese tasting from regional producers
• Wine tasting paired with the countryside
• Air-conditioned vehicle with WiFi and bottled water
• Professional English-speaking driver, no self-driving required

What to expect

You'll be collected from your Rome accommodation and driven south into Tuscany for roughly three hours. Once in Val d'Orcia, the landscape opens up—golden wheat, dark cypress, stone villages on the horizon. Pienza comes first: a compact, walkable town built around a papal vision, with a harmonious main square and cream-coloured buildings. You'll have time to wander. Then Montepulciano, perched higher, with narrower streets and views across the valleys. Between or after visits, you'll stop for cheese and wine tastings—genuinely local stuff, not tourist versions. Lunch isn't included, so choose a trattoria along the way or bring supplies. The drive home is the same scenic route in reverse.

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