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Following our day in Siena, we traveled 32 miles southeast to the Tuscan town of Pienza, our base for three nights. A UNESCO World Heritage Site, this quaint town of 3,500 residents is located on the crest of a hill overlooking the beautiful Val d’Orcia.


Established during the medieval period as Corsignano, the town was redesigned and renamed in the late 15th century by Pope Pius II. He enlisted the architect Bernardo Rossellino to transform the town to a blend of Renaissance and Gothic styles, and renamed it Pienza, which translates to “city of Pius.”
It was love at first sight! During our short orientation walking tour before dinner, Bruce and I were charmed by Pienza’s historic city center and were in awe of the breathtaking views of the valley below. We looked forward to exploring it further the following day, upon our return from Montepulciano.
Here is our first look at Pienza, the evening we arrived:


Several of us joined Ben on an optional walk after we returned from Montepulciano. The path we took bordered the town on the edge of the hill overlooking Val D’Orcia. The views were spectacular, and we came across an interesting cemetery along the way. I was intrigued by the effort loved ones made to keep each plot well-maintained and full of beautiful potted or planted flowers.
Following our group walk, Bruce and I continued to explore the historic city center on our own, walking literally every street within the walls. As Yogi Berra once said, “When you come to a fork in the road, take it.” And, that we did. Every. Single. One. So much pride and charm; from the doorsteps of homes to the adorable shops, it was quintessential Tuscany at its best!






Next up: MEDIEVAL MONTEPULCIANO