About this tour
Spend eight to ten hours driving through three of Tuscany's most celebrated hilltop towns: Montalcino, Pienza, and Montepulciano. Your private vehicle and English-speaking driver handle transport from your Florence or Siena accommodation, leaving you free to explore medieval architecture, rolling countryside, and local wineries and cheese makers at your own pace. Tastings and meals are arranged independently, giving you flexibility to choose producers that appeal to you.
Highlights
- Medieval town centres with Renaissance palaces and narrow cobbled streets
- Brunello di Montalcino and Vino Nobile di Montepulciano wine regions
- Pecorino Romano and aged Cacio di Pienza cheese producers
- Panoramic Val d'Orcia valley landscapes between towns
- Air-conditioned private vehicle with professional English-speaking driver
- Pick and choose wineries and cheese shops, or we'll suggest our favourites
What to expect
Your driver collects you early and handles the winding roads through Tuscany's southern valleys. You'll arrive in each town with several hours to wander, browse, and arrange your own tastings at local enotecas and caseifici. The pace is relaxed—there's no rushed group itinerary. Montalcino perches highest, offering sweeping views; Pienza was purpose-built as an ideal Renaissance town; Montepulciano tumbles down a ridge with wine shops at nearly every corner. You'll see grapes and olive groves, medieval gateways, and locals going about their day.
Good to know
Tastings and lunch cost extra and are paid on the spot directly to producers—this means you're not locked into pre-booked venues. Wear comfortable walking shoes; towns involve steep hills and uneven surfaces. The vehicle is fully air-conditioned. Request an infant seat when booking if needed. The tour is flexible and can be adjusted to suit your interests.
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.