Our trip was absolutely amazing. In 50 days of travel spending 1-3 days in each city and we had zero problems, near perfect weather (it only rained ONE day!) and the most fantasic time of our lives.
Some notes to travelers who are planning such an adventure and looking for tips:
1. DON'T bother trying to do your laundry in your room (as some experts say). Find a laundromat. It will save you so much time and give you time to plan out your next few days.
2. There is a FABULOUS hotel chain called "IBIS" all over Europe. More often than not the hotel room with a bathroom was the same price as two beds and a shared bathroom in a hostel. We, on averaged, paid 40 Euro to 55 Euro a night for the Ibis rooms. They were clean and fantastic with all the amenties of U.S. hotels.
3. People all over Europe are nice. We never had any problems so don't be afraid and NO we don't speak any foriegn languages and NO we didn't claim to be Canadian. If you are nice they will be nice.
4. Our Garmin GPS system worked fantastically and "walking" mode got us all over the city centers.
5. Ladies, you really really can get by with just a carryon backpack of clothing. Plan for dressing in layers and doing laundry every 4 days.
6. Also to the ladies - they have all kinds of US products over there: Tampons, pads, shampoo, lotion, I was so concerned they werent going to have my necessities so I packed 50 days worth. How foolish because I saw them everywhere.
7. Plan ahead but leave yourself some "cushion" time. I left 4 days of cushion time throughout the trip. A good thing because I was ill one day and delayed us a bit. It also allowed us a few days of utter relaxation.
Enjoy your trip!
In Milan, do NOT miss the Duomo. Possibly the most incredible place I've seen in all of my Europe travels. Allow at least 2+ hours inside to do a quick once over....4+ hours to really look at stuff and take it all in.