Concerning weather and wearing, I suppose we should keep in mind that you are Canadian. What we call "cold" shouldn't impress you so much. In practice, temperature seldom falls below 0 degrees both in Florence and Venice, unless you are unlucky. In Venice it could be windy, and surely wet.
The most visited cities, like Florence, Venice and Rome, are so used to guest tourists that there is no way to escape: you
will be a tourist, even if you come from 50 km away, simply because of your "I'm on holiday" face

. So, be an honest tourist - and enjoy it. Your look doesn't matter: remember that we have seen something worst anyway

Especially in Florence, be prepared: there is not a single church, museum, whatever for which you will not be asked to pay a ticket. Last autumn we (two) had to pay 45 euros in two days just for that .