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What characterizes friendship between women in early modern Europe, especially for a female ruler? Loyalty, fidelity, commitment, diplomacy, empathy, trust, bonds of reciprocity, of affection, of kinship? How does female friendship or collaboration impact on patronage and the arts, or on international diplomacy? This paper will explore these questions through an examination of the friendships and cultural collaborations that Maria Vittoria Leonora Feltria della Rovere (1622-1694), Princess of Urbino and Grand Duchess of Tuscany, developed with women at her court in Medicean Florence. The grand duchess also developed strong friendships and extensive networks with women throughout Italy and the Continent, from her ladies-in-waiting and nuns to noblewomen and royalty. With many of these, Vittoria maintained life-long relationships, deploying them as agents in her many cultural and diplomatic endeavors: as personal secretary, administrator and ambassador, as a purchaser of portraits from Rome or Turin, as buyer of clothing and luxury goods from France, and as chaperone for her ladies-in-waiting on their journeys to other cities or countries in pursuit of their own creative endeavors. Indeed, much of Vittoria’s life can be defined by her relationships with women, from her widowed mother, grandmothers, her aunt and future mother-in-law, to the sisters, novices, students, and other female members of the Medici family at La Crocetta, the convent where the young girl resided in Florence. Once grand duchess, Vittoria proved to be a generous benefactor, protecting women from abusive husbands and relatives, educating them in female colleges and convents, or promoting them as writers, singers, and artists at her own gynocentric court.