Hey there Travel-G,
It´s good that you´re planning ahead of time, because time will fly and before you know it, you´re in Europe!
Shoes definetly need to be broken in well before you head out on your trip. Especially, if you´re breaking in thick leather.
We had a topic on this a while back that may answer some of your questions. Here's the link- shoes/boots for backpacking
Hope it helps! B)