Isabella de’ Medici Orsini, daughter of Cosimo de Medici and Eleanor of Toledo, possessed beauty, charm and an engaging spirit. She was her father’s favorite child, well educated, and a lover of literature and music. She was a talented musician and was encouraged to master the skill of singing while accompanying herself on the lute. De’ Medici had a propensity for learning languages and knew Spanish, French, Latin and Greek, and was also proficient in speaking and writing in Tuscan. She married Paolo Giordano Orsini, an Italian nobleman from Rome, who chose to live his lavish lifestyle there, while she continued her Medici life in Florence. There, she had more freedom, culture, and protection from her family, particularly her father. De’ Medici staged entertainments, plays and musical events at the Palazzo Medici and Villa Baroncelli whether her husband was able to attend or not, indicating the depth of her freedom and desire to contribute individually to the cultural world in which she lived. De’ Medici sought the best performers for her court including female poets and singing groups that performed madrigals with the expressive emotions and suggestive nuance that was popular at the time.
Despite her independent and self-driven lifestyle, de’ Medici’s marriage suffered. In her 30s, she and Orsini had two children but once de' Medici's father died, she and Orsini entered extreme conflict about the well being of their children. Orsini, after all, was living an expensive lifestyle in Rome and was seeing other women instead of taking care of his family. De’ Medici also secretly spent time with a companion and lover, the handsome Troilo Orsini, her husband’s cousin, who visited Florence much more often than her husband did. Preferring to live in Florence, de’ Medici found countless reasons why she couldn’t join Paolo in Rome, including personal and family health issues. Eventually, Troilo was accused of murder and fled Florence for France. After his departure, Orsini’s power struggle came to an end when de’ Medici was instructed to join him on a hunting trip. With no more excuses to remain in Florence, she did as she was told and was murdered by her husband within days of her arrival.