Abstract: Before the advent of formal cartography, with its emphasis on observation and accuracy and its reliance on global standards, the itinerary was the height of geographic knowledge. These lists of cities and their relative distances, represented by many national “miles” or the location of postal waystations, opened European travel to a broad readership. This article traces the repetition and modification of route headings across a newly comprehensive bibliography of eighty-five itinerary books printed from the sixteenth through the eighteenth century. The application of Social Network Analysis (SNA) models the organizing logic of the itinerary genre and hierarchization of regions, cities, and routes. Digital methods prove to be key for moving between scales of consideration, from following the fate of one city, to many linked cities, to entire regions or the network as a whole. While the pilgrimage path of St. James and transalpine commercial routes were widely republished, dynamic networks based on the dates of first and last publication indicate the influence of new postal hubs, sea travel, and borders on early modern conceptions of a connected Europe. Instead of a sharp break brought by the Thirty Years’ War (1618–48), the 1620s saw the extension and diversification of routes, while the 1680s marked their curtailment. State-patronized cartography reshaped the genre, as authors and publishers increasingly incorporated maps into itinerary book production.