In wargaming there tends to be a payoff between terrain which is attractive and that which is practical for the moving of based figures acoss it. I try to reach a happy medium though this can take a bit of trial and error. Some of my hills are far too steep and troops slide down them like sinners into the inferno :)
I like to try to use some terrain features which are distinctive for an area. This is often the style of building being used. A certain amount of licence can be necessary since manufacturers do not necessarily make houses which exactly match a particular region or time period. Chimneys and windows can often show a building to be from a later period, but beggars can't be choosers.
For Italy I initially went for 10mm Timecast buildings. They are nicely made and based on real examples. I used 10mm because terrain scale is so far out of figure scale that accurately sized buildings for 15mm can be very big, especially churches. 10mm gives a good compromise, allowing a size which isn't too far away from figure scale but which lets you put enough buildings on the table to look like a small built up area.
A common feature of Tuscany and surroundinga areas is the hill top settlement. This shows my attempt at one