The fabric of the Roman empire was held together by a dense web of communications. Letters, often concerned with themes of connection and separation, played a significant role in the cultural construction of Roman imperial space. As material texts composed in one place and read in another perhaps far distant one, letters contributed to an understanding of imperial space articulated in terms of points on an itinerary, whose separation might be grasped in terms of time, as much as spatial distance. Strikingly ancient Roman letters almost never disclose an interest in the quality of places beyond Italy. Often letters work to efface the distance separating writer and addressee. In more formal letters little reference is made to distance, while letters between intimates frequently reflect on the capacity of this form of communication to transcend separation. What are the implications of this for conceptions of the empire’s space? Cicero’s letters are the primary focus of this discussion, which also touches on the letters of Seneca and Pliny and on Ovid’s exile poetry.