Traveling by private car and in the company of a local expert in history, art, and culture, this full day tour covers both the artistic and gastronomic highlights of the area. Tour Medieval and Renaissance hill towns and a Brunello di Montalcino winery, taste locally produced cheeses, all while enjoying spectacular panoramas along the way.

NOTE: This tour includes a car service that will pick you up at your accommodation.  Please tell us your hotel or apartment address in the 'additional details' box when adding the tour to your shopping cart.

Starting from Siena (or your accommodation in the surrounding countryside) we will travel together by private van to get off the beaten path and into the heart of one of the most scenic areas of central Italy. On our drive, we will learn about the origins of the region - a UNESCO world heritage site since 2004 - and the nearby Via Francigena.

We will stop and visit Pienza, a renaissance gem of urban planning and city design whose classical origins inspired the template of cities all over Italy and, by extension, the world. We will sample locally produced sheep's-milk or pecorino cheeses while exploring the town.  

Afterward, we will travel through the stunning countryside to Montalcino, a medieval village of ancient origins. Surrounded by fortified walls, this tiny stronghold was once a leather-making center of Tuscany and is now most famous for the vineyards beyond its borders. After a walk around the town center, we will sit down for a local lunch in a trattoria with our guide.  

After lunch, we will make our way to the Abbey of Sant’Antimo, a twelfth century benedictine monastery with eighth century roots - it is believed that Charlemagne founded the original church on this site outside of Montalcino. In the peaceful surrounds of the Tuscan hills, our guide will unfold this chapter of Italian history for us.  

We will complete our day with a visit to a local winery to see the operation and have a tasting while learning about the classification of Italian wines and understand the climatic conditions necessary to produce the Sangiovese grapes integral to Brunello wines.

The tour ends either back in Siena city center or at your accommodation.

For other historical and artistic explorations in Siena, we recommend our Introduction to Siena and Siena Palio tours. To continue exploring outside of Siena, we recommend taking a gander at our Introduction to Lucca and Introduction to Pisa tours.

We meet at your accommodation in Siena (or the surrounding area) at the beginning of the tour and drop you off at your accommodation at the end of the tour.  

Are the lunch and tastings fees included in the price of the tour? 

In order to maintain a degree of flexibility in choosing which shops and wineries we will visit, a tasting fee is not included. You will be responsible for the cost of any applicable tasting fees (wine tastings or cheese tastings), which are approximately €25/30 per person depending on your interests.  Lunch is not included in the cost of the tour, this will be at your own expense.

The tour is priced for departure from Siena or nearby. If you’re staying in Florence, please take a look at Day in Val D’Orcia (from Florence).