There are so many adorable, small Tuscan hill towns worth exploring — San Gimignano, Montepulciano, Volterra, Monteriggioni, and my personal favorite, Pienza.
Pienza is the perfect Renaissance town planned and built by Pope Pius II. It was originally a medieval town called Corsignano, but when Pius II became Pope in 1458 he decided to use his humanist education and immense resources to build an ideal city and a retreat from Rome.
Today Pienza retains its renaissance beauty and, although small, is a wonderful day trip from Florence. It so beautiful in fact that it was declared a UNESCO world heritage site. The city also sits on the edge of another UNESCO site, the stunning Val d’Orcia. This is the famous Tuscan valley used in many movies.
The city is also famous for its delicious pecorino cheese, which as you can see was the centerpiece for our picnic in Pienza. For a day of eating my way through Pienza I wore this wrap button up and my favorite denim skirt, which has been on repeat all summer long. I also wore these adorable, and perfect for Italy, espadrilles and this functional Mar Y Sole straw tote c/o Ship Chic.