About this tour
Spend eight hours exploring two of Tuscany's most photogenic hilltop towns in a private Mercedes with your own English-speaking driver. Travel from Florence to Montepulciano and Pienza at your own pace, calling in at a winery producing Vino Nobile and a cheese maker specialising in Pecorino. Your chauffeur provides local context as you wander medieval streets, taste regional specialities, and soak in Val d'Orcia views without the constraints of a group schedule.
Highlights
- Vino Nobile di Montepulciano tasting at a working estate
- Pecorino di Pienza cheese tasting and lunch
- Medieval Montepulciano and Pienza on foot
- Val d'Orcia countryside drive
- Private Mercedes with knowledgeable English-speaking driver
- Fully customisable stops and timing
- Door-to-door Florence pickup and drop-off
What to expect
Your driver collects you from your Florence accommodation and heads south towards the rolling clay hills of Tuscany. You'll spend a few hours exploring Montepulciano's steep, quiet streets and Renaissance piazzas before heading to a winery for a tasting. After, you continue through the Val d'Orcia landscape to Pienza, where you visit a cheese producer and enjoy lunch featuring local Pecorino. Throughout the day your driver shares stories and history, though the towns themselves are yours to discover at leisure. Roads are good but winding; bring water.
Good to know
Wine and cheese tastings, plus lunch, cost extra and must be arranged in advance. The driver is not a licensed tour guide, so expect local commentary rather than detailed historical narration. Both towns involve walking on uneven medieval cobblestones. Foldable wheelchairs only can be accommodated if you can independently enter and exit the vehicle.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.