When we leave Cortona, we will go south along the Val di Chiana to reach Montepulciano, hometown of humanist poet Angelo Ambrogini (1454-1494), known as "Poliziano"; the town is a true 16th century jewel, and you will be really amazed, while strolling along the Corso in the most typical Italian way, at the sight of the Renaissance Palaces and churches, rising to the top of the citadel, where the piazza Grande will surprise you with the "Pozzo dei Grifi e dei Leoni", the work of Antonio da Sangallo il Vecchio, a symbol of the alliance with Florence (the Lions).
A nice souvenir from here will certainly be a couple of bottles of the Nobile di Montepulciano wine, which is a typical Tuscan variety, along with the Chianti and Brunello. It might be good at this point of the itinerary to stop for the night or also a couple of days, and Chianciano Terme will welcome and spoil you with the healthy waters of its spas and mineral waters, famous since Etruscan times.
The itinerary will then proceed to the Val d'Orcia where the "ideal Renaissance urban design" of Pienza, on a hill with the background of the Amiata massif, the town transformed by Pope Pius II into a gem of rational urban planning. UNESCO declared the town a World Heritage Site, and the entire valley was included on the list of UNESCO's World Cultural Landscapes. Pienza was built on a village called Corsignano, which was the birthplace (1405) of Aeneas Silvius Piccolomini, a Renaissance Humanist born into an exiled Sienese family, who later became Pope Pius II. Piccolomini had the entire village rebuilt as an ideal Renaissance town, which became a model for other Italian towns and cities and eventually spread to other European centers.
After leaving Pienza, we can proceed then across the border with Umbria, where Castiglione del Lago rises on a cliff over Lake Trasimeno, the largest in the Italian peninsula, all surrounded by plantations of olive trees and vineyards. And inside Castiglione, you'll find traditional "trattorie" or open-air pubs, for a dinner in the breezy spring air.