Travel along the clay hills of the Crete Senesi and into the val d’Orcia. Walk the streets of Renaissance Pienza and enjoy the famous pecorino sheep cheese of the area with a Tuscan farm-to-table lunch. In the afternoon, visit the town of Montepulciano with its elegant churches, squares, palazzi and high walls and visit cellars hewn out from the ground beneath the city. Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity. Arrive at Pienza, one of the first towns to be entirely planned out on paper by important architects of the timeand spend your leisure time exploring the Romanesque church of Corsignano or the ideal, Renaissance Cathedral and walk along the scenic route overlooking the valleys and hills beyond.Visit 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 pecorino sheep cheese making processes, visit the farm animals and learn about the lifestyle of the area. Weather permitting, lunch will be served on a panoramic terrace, overlooking the valley below. In the afternoon, visit one of the biggest and proudest of the Tuscan hill towns, Montepulciano. This town was first under the dominance of medieval Siena and then became an ally to renaissance Florence. Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city, and taste the Vino Nobile. After a short walk around town with your guide, enjoy some free time on a second tasting of the Nobile wine or visit the town’s many stores, palaces, churches and streets. As you follow the main road down the hill, imagine 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, all the way to the top.