A few additional recommendations, albeit from someone with less direct experience than some posters here.
1)
www.mapmyride.com - you can sketch out your route and check the elevations. The elevations aren't completely accurate, but you can get a general idea of where you're headed.
2)
http://www.germany-tourism.de/cyclin...ermany_map.htm is an interactive map of various cycling routes in Germany. It's not specifically made for point-to-point but may give you some good ideas about specific routes.
My feeling is that you can very likely accomplish this, even solo, as long as you are prepared, pick a good route and keep your wits about you.
Originally Posted by Der Evan
As for training I think I'm in the green, back home in Arizona I was biking 35km a day with ease plus school and work. Now I'm looking at some routs through the alps but not sure where to start since I have no real touring expierence nor any with climbing hills. I have a Surly LHT stock with rear panniers packed with no more that 15-17kg.
With that much commuting you have a good base. However I highly recommend that you do some longer rides -- at least 50, possibly 70 if you think you can do it. Basically, this will get you mentally ready for some of the challenges on the tour.
By the way, while everyone varies, I've found that I tend to cover about 16km per hour when on tour. What you might want to do, if you have time, is do a weekend tour. That will give you a good idea of what gear and skills you need; what kind of things you can leave behind; give you an idea of how much ground you cover in an hour; indicate how many hours a day you want to ride.
Originally Posted by
scthomson
Having spent almost 10 years studying minority cultures in Northern Italy, Austria and Slovenija, I have to ask you what you motivation for this trip is.....
Seems pretty clear that he has two motivations: 1) get to Milan by bike and 2) tourism.
Immersion is great, for those who have the time; but it sounds like Evan has that one covered by his plan to spend 4 months farming in Italy.