Val D’orcia, Pienza and Montepulciano Tour

Visit the hidden gems of Pienza, Montepulciano and the Val D’Orcia in this full day excursion in Tuscany with an Italy’s Best driver.


  • Private guided day trip to two of Tuscany’s hidden gems, Montepulciano and Pienza, from Siena
  • Spectacular drive through the magical “lunar” landscape of the Crete Senesi
  • Discover the stunning Val d’Orcia, a UNESCO World Heritage Site and Tuscany’s most fertile valley
  • Typically Tuscan lunch and a tasting of Pecorino cheese, Pienza’s pride and best known product, at an organic dairy farm that, in addition to delicious cheese, boasts spectacular views of the valley below (optional)


Full Day in Tuscany

Pienza, a UNESCO World Heritage site, is rarely frequented by tourists, and you with experience this hidden Tuscan gem on your Pienza tour. Florentine Renaissance architect Bernardo Rossellino created Pienza for Pope Pius II, and the stunning architecture evokes a movie set. Filmmakers seem to agree as Pienza served as a location for “The English Patient” and “Romeo & Juliet.” Visit the Museo Diocesano and the Duomo for fine Sienese art then see Palazzo Piccolimini the Pope’s family palace with a design inspired by that of Alberti’s for Florence’s Palazzo Ruccellai. You’ll notice the distinct smell of pecorino, or sheep’s milk cheese, as you make your way around town. The cheese is produced nearby and sold in Pienza’s many artisan food shops.

Montepulciano Tour

For years, the Florentines and Sienese fought over Montepulciano, the capital of the Val d’Orcia region and perched atop a narrow ridge of limestone, sitting close to 2000 feet above sea level. Montepulciano eventually went to the Florentines and their influences are found in the stately Renaissance architecture that lines the streets. Your private guide from Italy’s Best will lead the way showing you the Michelozzo designed town hall, reminiscent of Florence’s Palazzo Vecchio as well as explaining the crucial role wine-making has played in Montepulciano’s history as its known for Vino Nobile di Montepulciano, a great Tuscan red produced nearby. Feel free to pick up a bottle or two in of the towns many wine shops that dot the streets before meeting your driver to return to your accomodations.

This is just an example of our Val D’Orcia, Pienza and Montepulciano tour. For different pick up/ drop off locations or customized itineraries we invite you to contact one of our tour coordinators to help you design your own tour.