The earliest directional map I know of is the famous “Peutinger Table.” In the late first century B.C., Marcus Vipsanius Agrippa produced a road survey and map of the world for Emperor Augustus. None of the original maps has survived, but a later version was found near the end of the fifteenth century and eventually found its way into the library of Konrad Peutinger (fl. 1508-47). Though that map is now lost, copies of various cartographers and modern facsimiles have been made.
The Peutinger Tables consist of eight sections depicting the world along the primary roads of the Roman Empire. The area shown extends from the southeast corner of England—part of the first section showing the rest of Britain having been lost—to Ceylon, the eastern edge of the known world. Reflecting its source in Agrippa’s road survey, the map is drawn around the roads, which are laid out in a schematic fashion—not dissimilar to the way the lines are laid out on the famous tube map of London—though here the roads are put down mostly in a horizontal direction, creating a map that is essentially a long, narrow strip. The Roman roads are given in detail, each notched to indicate a day’s march, with the places and camps one would come to if traveling on those roads. Really, very similar in intent and execution to a triptik.
Another place one finds itinerary maps is from explorers, who would make maps they surveyed along their routes. These surveys would often be amalgamated into area maps, but they also were sometimes issued as itinerary maps. James Hervey Simpson mapped a route from Fort Smith, Arkansas to Santa Fe, producing a map in 1849 which was intended as a wagon road itinerary map for emigrants and traders.
Another example of that is the seven sheet map drawn by Charles Preuss based on the surveys and notes made during John Frémont’s expedition along the Oregon Trail in 1842-43. These maps were combined into the Preuss/Frémont map of 1845, but the seven sheets were very much in the tradition of an itinerary map intended for use by the many emigrants along the Oregon Trail, as well as 49’s heading off to the gold fields of California.