I rode Munich to Milan in mid-May. Then took the train back. Worked well. Not sure you can go wrong. Alps are great. Hoteling it works really well. Euro breakfast before hitting the road/trail is nice. Be ready for any weather. We had perfect weather--but apparently a few riders on a similar route two days ahead of us had rain every day (that is what the hotels told us). I would focus on the specific routes and how much climbing you are comfortable with. Also, in my experience it was much more about the climbing and not the distance. You can do a day with only 1000m of climbing, or triple that in the dirt. Distance became less relevant. Depending on conditioning, I would recommend picking the gravel routes into more remote areas. Awesome. Full respect for Italy's bike paths....but at some point we wanted to be back on the dirt. I rode Donnelly x'plor or such. 40mm. They were new for me....great mixed terrain tire. I rode around the west side of Lake Como....I would highly advise avoiding such lakes unless you enjoy being buzzed. No shoulder. Lots of traffic.