I am planning a trip (2nd time) to italy starting 2nd week october for 19 days. We are starting in Zurich (free tickets) and plan to go from there down to Como. I am torn between going from there to the Piedmont or to Garfagnana, on the way to Chianti. From Chianti we will loop back up north, going to Venice(2 nights) before heading back towards zurich. So what should it be, Piedmont or Garfagnana?

Well, it should be up to you to decide, according to your interests and desires. Personally, I wouls do both and skip Chianti, though.