Tuscany Dream – Worldwide Luxury Travel Agency

Small Group to Pienza and Montepulciano From Siena

A full day tour immersed in a picture-postcard paradise! Meander through the rolling clay hills of Crete Senesi and ascend through countryside villages, until we reach the peak of Pienza where you can stroll through morning-lit streets. Eat a customary Tuscan lunch on a farm and feast on the region’s well-known pecorino cheese. Later during the afternoon, visit statuesque churches, piazzas, palaces and marvel at the architecture of Montepulciano. Did you know that there are cellars underneath the city itself? The gathering place is at Siena’s Basilica of San Domenico at 9:30 a.m. which is a breeze to find if you are coming from another town or driving with your own vehicle. There are parking facilities available in the nearby area. Convene here with the driver guide who will accompany you for this tour. Let your eyes revel in one of the most beautiful routes in Tuscany as we leave Siena via the Crete Senesi’s moonscapes. We indulge you with short stops to allow for plenty of photos before we visit either a charming feudal hamlet which few tourists have seen, or a monastery of Benedictine monks. We then visit the Val d’Orcia, a UNESCO World Heritage site, where some of the views have been memorialised as Tuscan postcards. Onwards to the idyllic town of Pienza which is reminiscent of the Renaissance period. This town was among the first to be planned by the significant architects and artists of that period. They were solicited by Pope Pius II, a humanist, who wanted these progressive thinkers to assist him in renewing his home town and help him to revive it to new heights. Pienza is correctly viewed as the Renaissance masterpiece of the Val d’Orcia. Take the time to see the Romanesque Corsignano Church, or enjoy some retail therapy and take in the picturesque avenues of this tiny village. Leaving Pienza, we head to a regional dairy farm. There we will enjoy a nourishing and inspirational lunch which will consist of fresh farm produce. It is the perfect opportunity to learn about the cheese manufacturing process, animals on the farm and the local way of life. Should the weather allow it, we will dine and enjoy lunch on the terrace which provides stunning views. Occasionally, the farm is inaccessible on a particular day. For that reason, we will make the most of a customary Tuscan meal in a typical trattoria and then enjoy the famed pecorino cheeses at a different location. The large Tuscan town of Montepulciano is our next stop. First governed during the medieval times by Siena, followed by Florence during the Renaissance, the impacts of both these cities is evident in the town’s art and architecture. Montepulciano is situated on a precipitous hill which has unmatched vistas of the border of Tuscany and Umbria. We explore Piazza Grande, the town’s main square, and discover one of a myriad of old wine estates in a nearby area. Elegant and with a wealth of distinguished palaces, this town once teemed with nobility that resided in this region. The guide will lead you on a short tour of the town. Thereafter, you can enjoy some unescorted down time where you could try Montepulciano’s “Nobile”, enjoy some retail therapy, roam the streets, visit shops and churches, and get to know the town.

  • WHERE: In front of San Domenico Church in Siena
  • DURATION: 8 hours
  • STARTS • 09:30 AM


  • Let your eyes revel in one of the most beautiful scenery in Tuscany: the Crete Senesi’s moonscapes and the glorious Val D’Orcia
  • An explosion of taste: Nobile di Montepulciano wine, Pienza pecorino cheese and a delicious lunch served in a dairy farm


  • Journey by fully-fitted minibus
  • Professional driver/tour leader
  • Free time in Pienza and Montepulciano
  • Lunch served at a dairy farm
  • Cheese tasting in Pienza
  • Nobile di Montepulciano wine tasting
  • Visit to historical wine cellars

Notes and Advices

  • Occasionally, because of accessibility or a spur of the moment change of plans, the day’s agenda may differ slightly. If such a situation does arise, the excursion will be somewhat adjusted. Nevertheless, the tour will remain much the same, unchanged in timeframe and will include equivalent considerations
  • Comfortable shoes suggested
  • Please inform us of any food intolerance or allergy in advance