This book combines the history of charitable institutions with the study of power in urban and rural spaces from the late medieval to the early modern era. Focusing on the Ospedale di Santa Maria della Scala in Siena, the book goes beyond examining hospitals in an urban context to also consider the significant impact of charitable institutions in rural spaces. Case studies of Santa Maria della Scala's farms allow an investigation of the relationship between urban institutions and their rural properties, while looking at subject hospitals outside the Sienese state offers a glimpse into the competition for power with non-Sienese entities. As Siena's politics shifted in the sixteenth century, Santa Maria della Scala and its rural spaces became sites where power was negotiated. The book thus demonstrates how geographies of power affected the practice of charity for both urban hospitals and the rural communities they influenced.