Here is a simple one:
Joining the V/F/R tour in a few weeks.
I'm making my wife nuts, as I am anxious about pick pockets, but all of our friends who have traveled to Italy have not had an issue.
I've over-analyzed the different front pocket wallets, that wallet that flips into your pants, and the money belt that is under your shirt.
I'll have a backpack that I'll have a simple lock on as a deterrent.
Here is the question: when heading out for the tour, do you carry your passport, or is there a hotel safe? If I need to carry the passport, then that changes everything... if don't need to carry it, then keeping some cash and a card in the backpack, and then some in front pocket... might be ok
Or is it safe to have the passport in my backpack? ugh.
I've lost it. :)