Good to hear you enjoyed reading this anyways! :) The big picture in summary is, that we traveled around Italy and worked through Workaway (you guessed right! Or did I write it there, can't remember anymore and I'm too lazy to check?). Our first job was in Montefiascone and really was an educative experience in many ways (culture-wise aswell). Some cities we just visited during our freetime and after we finished working with them.
I can highly recommend trying workaway or some similar organization (btw there's also some sites for house sitting)! It's much easier to find a job through some of these organizations as a foreigner. Especially if you don't know the language or don't have any contacts with locals at first.