Montalcino & Pienza

What about…



In general, we suggest a a full day tour (8-9 hours).


Suggested itinerary (full day tour)

The order of visit of the towns will depend on the geographical position of your accommodation.

At a first glance, this tour could be easily labelled as the perfect tour for food and wine lovers. Indeed, this excursion should be seen as the consequent and natural extension of the Chianti tour.

In this tour, one genuine Brunello winery will be recommended along the way. Winemakers will give you detailed information about Brunello wine, leading you around their estate and down to the cellars. Reservation in the wineries is always required.



Built on top of a hill as a military outpost, Montalcino is blessed with an incredible view over the quiet Val d’Orcia. Gently resting on a hilltop 564 meters above sea level, the town was the major market place of the Middle Ages in the southern area of Siena. Today, it still preserves this commercial feature thanks to the production and marketing of its unique wine, the Brunello, a worldwide famous red wine of excellent quality.

In order to visit Montalcino from its origin, we will first take you to the Fortress, on top of the hill. Shaped like an irregular pentagon, its tall walls are punctuated by five towers overlooking the entire valley; one of the tower is actually today occupied by a peculiar winery.

After the Fortress, the visit proceeds in the historical centre. A labyrinth of medieval streets, the winding alleys of the town can be avoided in favor of the more accessible via Giacomo Matteotti, full of local shops and eating places. Proceeding straight ahead, you will soon encounter the Palazzo Comunale, with its characteristic, slender tower topped by the “Campanone”,  and the Gothic Loggia of Piazza del Popolo.

Keep strolling along the medieval alley; at the end of it, you will find us waiting for you. And if you still feel like visiting more churches, a short ride in the car will give you the chance to see also the Cathedral, the Church of Sant’Agostino and the Church of Sant’Egidio.

Only Driver - Montalcino Tour




First example of Renaissance town planning, the small village of Pienza is called after the name of its founder, Pope Pius II, who explicitly commissioned a Florentine architect to build the ideal city in the site of his native village, previously called Corsignano.

Since Pienza is entirely a pedestrian area, we will drop you off at the gate of the town and wait for your return here. Following Corso Rossellino, you will soon encounter the key buildings of Pius II’s project: the Cathedral in the middle of the square, and then clockwise, the Palazzo Piccolomini, the Palazzo Comunale, the Palazzo Vescovile and the Palazzo dei Canonici.

Taking the path between the Cathedral and the Palazzo dei Canonici, a natural terrace overlooking the Val d’Orcia offers you the perfect panoramic spot over the quiet valley. In good weather conditions, the shape of the Mount Amiata can be spotted in the background, together with the Rocca di Radicofani on the left, and Montalcino on the right.

Before heading back to the car, take a stroll along the two main streets and look for a cheese tasting place: the Pecorino di Pienza, a unique sheep’s milk cheese, is considered the best pecorino produced in the Crete Senesi, and perfectly matches the chestnut honey from Montalcino and the wines of the region, from Chianti to Brunello.


Only Driver - Pienza Tour


Please note that meals, tastings tours, entrance tickets to museums or churches, and tip to the driver are not included in the price we quote.