Uguccione V, the second son of Ruggero Ranieri di Sorbello (1864-1946) and Romeyne Roberts (1878-1951), was born in Florence, Italy on 22 February 1906. He spent most of his childhood traveling back and forth between Rome and his family’s estate in Perugia, Italy. His schooling began with private lessons in Perugia and sometimes attended classes with other local children at the Pischiello school on Lake Trasimeno. Around age nine, Uguccione had his first taste of formal schooling at De Merode School in Rome. Uguccione spoke English at home with his British nannies and American mother. His schooling in Rome refined his knowledge of multiple languages, which would benefit him later in life when he traveled to the United States.
In 1922, when he was sixteen-years-old, Uguccione took some time away from school due to a “weakness of the eyes” and accompanied his Grandmother Charlotte to the United States. As a scholar and student, Uguccione had already been to many places throughout Europe, but he described his first trip to America as “truly like visiting another world.” In his short autobiographical piece I Start Remembering, Uguccione described his experiences abroad:
New York was a wondrous town to my eyes of sixteen. Its buildings were already so much taller than anything I knew in Europe — and I don’t mean the sky-scrapers but just the ordinary apartment building which bordered lower Park Avenue (and which have now been replaced by glass office buildings). Even at that time the city gave me that feeling of infinity which it still does. And New York is a wonderful town to be young in!
During this trip he attended parties in New York, visited cousins in Philadelphia, and saw world-class eye specialists in Washington D.C. and Baltimore. After an enjoyable summer, Uguccione and his grandmother went on to England in October. During his first trip Uguccione had already fallen in love with America.