Pickup directly from your accommodation or preferred location in Florence. Meet your English-speaking chauffeur, who will be at your disposal for the full day in a luxury Mercedes-Benz sedan or van. During the drive, your chauffeur will share historical context, local traditions, and insights into the Tuscan countryside you’ll be crossing.

Arrive in Montepulciano, a stunning hilltop town known for its Renaissance palaces, stone streets, and sweeping views over the Val d’Orcia. You’ll have time to stroll through the historic center, explore small shops, and enjoy the atmosphere of one of Tuscany’s most elegant wine towns. Highlights you may see include : Piazza Grande, Historic palazzos and noble residences, Panoramic viewpoints over the countryside

After the town visit, meet your driver and continue to a local winery just outside Montepulciano. Here you’ll enjoy a tasting of the area’s most famous wines, including Vino Nobile di Montepulciano, produced from Prugnolo Gentile grapes and known for its structure, elegance, and aging potential. The tasting is typically accompanied by local products such as olive oil or light Tuscan appetizers. Note : Wine tasting is not included and is paid directly at the winery. We reserve the visit in advance.

Continue through the rolling hills of the Val d’Orcia to the Pienza countryside, where you’ll stop at a traditional local cheese factory. Here you can enjoy a tasting and lunch centered around Pecorino di Pienza, one of Tuscany’s most celebrated sheep’s-milk cheeses, often paired with honey, jams, cured meats, and local wine. Pienza is known all over the world for its production of 'pecorino cheese' and for its traditional Tuscan cuisine. Note : Tasting and lunch are not included and are paid directly on site. Reservations are arranged in advance.

In the afternoon, your chauffeur will take you into Pienza itself, a UNESCO World Heritage town designed during the Renaissance as an “ideal city.” Enjoy free time to stroll through its elegant streets, artisan shops, and scenic terraces overlooking the Val d’Orcia. Highlights you may see include : Piazza Pio II, Pienza Cathedral, Panoramic viewpoints over the Val d’Orcia

Relax during the scenic drive back to Florence, with drop-off at any location of your choice.