About this tour
Spend a full day touring Southern Tuscany's three signature towns, tasting what makes the region distinctive. Begin in Montepulciano at a working winery sampling local reds, move through Pienza's hilltop centre to a sheep-dairy farm for pecorino cheese, then finish at a family olive mill near Chianciano pressing and tasting extra virgin oil. Hotel pickup and dropoff from Rome included; choose between private groups or shared transport.
Highlights
- Montepulciano winery visit with wine tasting and producer insight
- Pecorino cheese made fresh at Pienza farm, farmyard-to-table
- Chianciano olive mill: watch pressing, taste oils of different ages
- Three medieval hilltop towns in one loop
- Air-conditioned vehicle with English-speaking driver throughout
- Hotel collection and return to Rome included
- Flexible private or shared group options
What to expect
Your driver collects you early from your Rome hotel and heads south into rolling Tuscan farmland. In Montepulciano, a licensed guide walks you through a working winery, explaining how local grapes become the wine in your glass—you'll taste several vintages. Next, you'll drive to Pienza, a compact Renaissance town perched above the Val d'Orcia. A farm visit focuses on pecorino production; you'll see the curds and ageing caves, then taste wheels at different stages. The final stop is an olive mill near Chianciano, where you'll observe crushing and pressing before sampling oils—often weeks, months, or years old. The pace is leisurely; expect roughly 2–3 hours at each location with town-wandering time between.
Good to know
Book the private option if you want route flexibility or speak to staff about customising stops. Shared tours run fixed itineraries with up to 8 people. Wine tastings require proof of 18+ years; under-18s receive soft drinks instead. Infant car seats available on request. Tipping is not mandatory but welcomed. The drive is comfortable and air-conditioned.
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.