I have visited this pearl many,many times, and I will return: Pienza, south of Siena in Tuscany, is a small village, but has everything an Italian village should have: History, romantic streets, art, small shops, enotecas, good restaurants.... and a fantastic view over the Val d'Orcia. Both Pienza and Val d'Orcia are on the UNESCO's World Heritage List. Pienza is very small, so you can reach everything without getting tired.
Pope Pio II (Aeneas Silvio Piccolomini) decided to reorganize this village,called Corsignano, in which he had grown up, and engaged the architect Rosselino to construct a town built after the ideal principles of the renaissance. This was in 1449, 9 years before the pope was elected. Today you can visit Palazzo Piccolomini, the Duomo, and other historic buildings. But walking slowly in the narrow streets, where every buildings have flowers outside, and the names of the streets are so romantic and special, is probably the best for me. And buy some of the famous Pienza peccorino cheese, local salumi, wines from the area,- the brunellos, the vino nobiles, the chianti classicos...and just enjoy a nice meal at one of the restaurants, it is the good life!