Your meeting point is at the Basilica of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town or with your own car as there is parking in the vicinity. Here you will meet the driver guide for the start of the tour. We head out of town on one of the most panoramic roads of Tuscany through the characteristic moonscapes of the Crete Senesi. Brief stops on the way for photo opportunities before visiting a quaint non touristic small medieval hamlet or a Benedictine monastery. Then enter the UNESCO heritage site of the Val D’orcia valley where you come across some of Tuscany’s most famous postcard pictures. Arrive to the beautiful utopian renaissance town of Pienza, one of the first towns to be entirely planned out on paper, by important architects and artists of the time, called upon by Pope Pius II the humanist pope, to help him in renovating his native town and bringing it to new splendor. Pienza is rightly considered the gem of the renaissance in the Val d’Orcia. You will also have the opportunity of viewing the Romanesque church of Corsignano or spend your time shopping and enjoying the pretty alleys of this little town. After Pienza we make our way to a local dairy farm for a wholesome and refreshing lunch based mainly on the fresh ingredients produced on the farm. Here you can learn about the cheese making processes, visit the farms animals and learn about the lifestyle of the area. Lunch will be served on a panoramic terrace, weather permitting. It could occur that the farm for some reason is unavailable on the day. In this case we will enjoy our traditional Tuscan meal in a characteristic trattoria and then try the famous pecorino cheeses separately. In the afternoon we visit one of the biggest of the Tuscan hill towns, Montepulciano. This town was at first under the dominance of the medieval Siena and then under the renaissance Florence, here you can recognize the influences of both towns in its architecture and art. The town is located on a steep hill overlooking the amazing views of the Tuscany - Umbria border. Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city. This noble town is rich with many important palaces owned by the noble families that lived here. After a short walk around town with your guide you have free time for tasting the "Nobile" of Montepulciano or passing time visiting the town and its many stores, palaces, churches and streets. As you follow the main road downhill you can try to think of how hard the “Bravio delle Botti” town festival must be, a competition between the neighborhoods of the town that race wine barrels from the bottom of the hill to the top.
On some occasions, due to availability or last minute changes, the itinerary might vary a little. In this case the tour could be modified slightly. However the day will maintain a similar general imprint, same duration and have all the same inclusions.