I've started to map the route. I did this in a few stages, firstly looking at spots where family are, secondly looking at spots where awesome things are (UNESCO world heritage sites for example), and thirdly by looking at flickr and looking at other awesome looking places.
Then I tried to see how whatroute could take me through all these awesome places without doubling the distance. Here is a link to my effort so far (it is incomplete as of posting). It has so many markers that you have to click across at the bottom to actually see all the points (and the route). So far it goes from Rome to about Besancon in South East France.
You may also note that it goes over about twice as many Alps as is really necessary... this is entirely because I want to go to Chur, to see this awesome railway:
Big thanks also to Andrew Sykes whose research and planning formed the basis of my route!