Embark on a breathtaking journey along one of Tuscany's most scenic routes, winding through the lunar-like landscape of the Crete Senesi. Our destination is the charming medieval hamlet of Pienza, nestled in the picturesque Val d'Orcia valley. This charming town was one of the first to be meticulously planned on paper by esteemed architects and artists of the time. Commissioned by Pope Pius II, the humanist pope, Pienza was transformed to restore its former glory. After working up an appetite, indulge in a delicious lunch featuring fresh local ingredients on a picturesque farm terrace (weather permitting). In the afternoon, we'll make our way to Montepulciano, one of Tuscany's largest hilltop towns. Having been under the influence of Siena during the Middle Ages and Florence during the Renaissance, Montepulciano is now famous for its exceptional wine. As we explore the historic center, perched on a steep hill, notice the architectural and artistic influences from both Siena and Florence. Visit the grand Piazza Grande, tour one of the many underground wine cellars, and discover the stately palaces of the noble families who once called this town home. Savor a taste of the esteemed Vino Nobile wine and then take some free time to wander the streets, palaces, and churches at your own pace. As we make our way down the hill, imagine the excitement of the "Bravio delle Botti" festival, where locals race wine barrels up the steep hill!