No, the phrase “itinerant preacher” has a derogatory ring to it as some aimless wonderer.
Maybe to you. That Jesus WAS, in fact, a "street preacher" who spoke to crowds where ever and whenever he could and he was NOT a specific pastor of a specific church, then he WAS an itinerant preacher like his cousin, John the Baptizer as well as Peter, Paul, Andrew, Thomas, etc.. It didn't make any of them "aimless wanderers". They each had a God-ordained mission that took them many places and they fulfilled their roles.
Oh my friend, how utterly wrong you are. Some of the sweetest, saintliest men of God that ever lived were itinerant preachers. Circuit riders, often called, because being itinerant just means having somewhere to go, by careful planning, and regularity, just like Jesus and Paul, only with horses, and not your supposed aimless wandering, which is nothing but a fiction. Some of our American circuit riders were instruments of God in the Second Great Awakening, among whom I can count one of my great great grandfathers. Godly men whose sincere and powerful preaching of the word by the Spirit of God brought the light of the Gospel to rich and poor, in the cities and the mountains, famous generals, humble shopkeepers, wherever they were needed, men who were twice as poor as average poor preachers, having no steady place to call home and care for a family of their own. But they cared for the family of God, and they will have their reward accordingly.
Peace,
SR