This chapter addresses the question of hospitality as it arises in A Month in Siena, Hisham Matar’s memoir of his sojourn in the historic Tuscan city. Grounding a reading of the memoir in philosopher Massimo Cacciari’s question—what do we ask of the city?—Norbert Bugeja opens up the aesthetic and political dialectics that shape the affinity between the city and its memorial subject in Matar’s book. The hospitable character of the Italian city and its famed works of art does not emerge from an expectation that it could hold forth some defined schema of closure for Matar, who walks into the city in the wake of a previous memoir (The Return, 2016) that portrayed his tortuous quest for answers about his father’s disappearance. Here, instead, Siena’s hospitality makes itself felt in the manner in which the city—at once socius and realm of art—is seen to partake, to a heightened extent, of that which has already suffered brutal estrangement within the memorial subject’s own story, and his thwarted consciousness: the hope for good government, for the triumph of justice, for the demise of obscurantism. The aesthetic of empathy that is intrinsic to Siena as a complex cultural polity is what ultimately enables the city to morph, pace Cacciari, into a civitas augescens: a city that, by virtue of the ability to delve into and trace within its cultural self the conditions that gave rise to the estrangement of those knocking at its doors, “is always growing,” expanding its self-definition to include a legitimation of strangership as a mode of affiliation across times, spaces, and contexts.