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
The tower was scratchbuilt using textured card from Slaters. The roof was made by texturing some milliput - this took ages!
The hill was made from extruded polystyrene. This is much tougher than the white expanded polystyrene and carves well.
I may well make another at some point, with one side vertical to allow the hill to be placed against the table edge as a part of a larger city. This will also allow a larger area on top for the placement of more buildings with even more levels.
I'm still not sure I like the green building, though I based the colour on a 14th century picture by Fra Angelico.
One reason I'd like to have more area for buildings is that I bought quite a few JR Miniatures buildings from Magister Militum . These are 15mm but, as with many ranges of buildings, they are slightly underscale - especially when most '15mm' figures are now larger.
They fit in very well with the 10mm Timecast buildings:
Another key feature of this landscape is the olive grove. I bought some trees from Realistic Modelling Services.
As with the buildings, I bought ones which are underscale. This emphasises the difference in height between the olive trees and ones in woods - like most people I use trees which are substantially undersized at perhaps 5 time the height of a figure rather than a more realistic 10 or 20 times taller. I have some poplar trees too, from the model tree shop though I haven't yet based these.
I scratchbuilt some vines.
These are based on 'tongue depressor' style sticks. I drilled a number of holes along the length and put in some thick wire uprights. Wooden poles would have worked too but I wanted something fairly thin and strong. I then used some Woodland Scenics Fine Leaf Foliage. This comes on twiggy material which can be selected for the most vine like strands. A couple of pieces of this placed horizontally give good cover. I made half a dozen or so of these in about an hour and had loads of the foliage left over. I put them on a piece of painted and textured MDF to show the extent of the vineyard. Sometime I may make some hills with terraces onto which I can put some narrower versions of these strips.