Day trips from Rome

Tuscany Wine & Cheese Tour in Pienza | Private

Taste your way through the jewels in Tuscany's crown - Montepulciano or Montalcino and Pienza.

  • Availability

    On Request

  • Duration

    Full Day

  • Start time

    On Request

  • Private tour

    On Request


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Why Choose it?

  • Discover Pienza: a stunning 15th century town and the capital of pecorino cheese.
  • Explore Montalcino or Montepulciano - two towns that have aged as well as their wines.
  • Journey through the Tuscan countryside in private luxury with an expert guide and driver.

Tour description

Indulge your palate in some of the low-hanging fruits of Pienza, Montalcino or Montepulciano. This full-day private tour from Rome or Florence transports you deep into the Tuscan countryside for a culinary and cultural adventure around Italy’s most viticulturally renowned region.

Driving through Tuscany is an experience in itself. As you cruise along in your air-conditioned car, your journey leads you through a landscape of rolling hills, wild olive groves, and bursting vineyards. But it’s what awaits you that makes the journey really worthwhile.

Discover the 15th century town of Pienza

We first reach the town of Pienza which, thanks to the generous patronage of Pope Pius II, is one of the most authentically Renaissance towns in Italy. We visit the main square, home to some of the towns most evocative buildings: the Duomo, the Palazzo Comunale,the Palazzo Borgia, and the Piccolomini.

We then soak in the stunning panoramic views over the beautiful Val d'Orcia and indulge in a lunch involving some delicious 'pecorino' (cheese made with sheep's milk) - Pienza's globally beloved local product.

Marvel at the wonders of Montalcino

Just an hour south of Siena, across folding hills and winding rivers, stands the medieval hill-town of Montalcino. It’s an affluent town, sustained by the trickling effects of world-renowned viticulture and a steady stream of local and international tourism. Yet it’s also unspoilt - a true Tuscan treasure dotted with enoteche wine bars and quaint delicatessens.

Montalcino’s most famous export is its Brunello di Montalcino. Made from 100% sangiovese grapes, this DOCG wine (Denomination of Controlled and Guaranteed Origin), which boasts considerable longevity, is enjoyed throughout the world. Taste it here at the source, accompanied by a special pairing of cured meats and select local cheeses.

Or lose yourself among the magnificence of Montepulciano

Instead of Montalcino, your private tour can stop by the town of Montepulciano. Best known for its eponymous wine, this medieval walled city is just as ripe in Renaissance architecture. Climbing one of its vantage points for a breathtaking panoramic over Chianti is truly an unforgettable experience.

The vineyards surrounding Montepulciano’s walled centre produce some of the best wine in Italy. Indulge to your hearts content with as you pair these wines with a range of select regional delicacies before we make our scenic journey back to the Eternal City.


Car/van/limo with English-speaking guide & driver


  • Pienza
  • Montalcino or Montepulciano
  • Cheese and Wine Degustation

Wheelchair accessible:

Yes. (Itinerary may differ).

meeting point:

At your hotel

see on map

excellent guides

Our guides are fluent in English and have a contagious passion for the inspiring cultural heritage of our Italian cities. Experts in their fields, they will immerse you in the hidden histories and intriguing lives of history's great protagonists. So much to see, so easy to miss out: with the help of our guides, visit the most absorbing sites and uncover the stories that have changed the world. Don't miss this fascinating journey!