This chapter will introduce Vittoria della Rovere at the Medici court, during the first period of female regency in Medici history. Her biography will be followed by an examination of her education by the Medici Grand Duchesses, her grandmother and aunt, her learning and erudition as evidenced through her private library and her own role as an educator of her children and grandchildren. Her governance at court will also be addressed. I will argue that a matrilineal model of education and governance operated at the Medici court from the 1620s on, and that the Grand Duchess was a significant exponent of this gendered dynasty of ruling women.