Level: HardTravel until you acquire the Traveler trait. The Wanderer track is easily leveled by travelling a lot. The Seasoned track requires encountering Danger events while traveling, so ensure your Caravan Master and travel options do not make travel Safety too high, and then plan travels which make detours through provinces with appreciable Danger. It's possible to modify the route while the travel is ongoing to make further detours towards short-lived dangers like battles and sieges. Choosing the safest options in Danger events may lead to reduced or zero Seasoned experience.
Credit to
Bayek von Kuwaq on Steam for his
guide.