Itinerant rule, a form of rule that is exercised through travelling the states’ territory, was a common pre-modern form of governance under the condition of weak centralized administration. Yet, not much is known about the characteristics and determinants of rulers’ itineraries. We argue that rulers maximize the payoff of their travelling by targeting areas lacking trustworthy agents that could substitute for the ruler’s physical presence. We test this argument focusing on the emperors of the Holy Roman Empire between AD 751–1519. We reconstruct emperors’ itineraries through information on ca. 145’000 documented, dated, and geolocated activities they engaged in. We geographically locate emperors’ closest agents by recurring to their immediate family members (uncles, aunts, siblings, and children) via their (time-variant) titles. Taken together, these data allow us to estimate the effect of the geographical spread of an emperor’s agents on his travels, both within and across reigns. Variation in the natural death of family members and emperors allows for causal identification within and across reigns, respectively. The results of our analysis will shed light on an understudied pre-modern political phenomenon that leaves its trace in the travels of statesmen and -women today.