I am planning a trip to Northern Italy in which I arrive in Milan at 8 AM on 4/30 and depart for home at 10 AM on 5/12. Normally I do open jaw flights with two locations, but RT this time seemed to be the best option, geographically and economically as well. I want to see Milan (in particular the Last Supper) on either front or back end of the trip, and in order, Venice, Florence and the Cinque Terre and back to Milan, all by train. I have driven in Scotland and France so renting a car is not a problem for me if there is something off the beaten path to see. I've never been to Milan or Venice so I'm open to anything there. I'm returning to Florence and the CT to see and do things I was not able to do on family trip there. In Florence, for example, we missed the Baptistry, the Duomo Museum and the Monastery of San Marco, and I want to see David again. In the CT I want to hike some of the trails and just relax. I've planned four other trips with wife and her mother using the Travel Forum and hope I can get some help from you on this, my first ever solo trip out of the US. Do you think my proposed itinerary is workable and if so, can I plan this trip in such a short time period? My other questions:
1) How much time should I allow in each place?
2) What are your "must sees"?
3) Can you please recommend hotels or B&Bs? Cost not a problem but I like simplicity.
4) Is working in Switzerland or Lake Como possible?
5) Rail pass or point to point tickets which I've never done? On other trips I've gotten a first class rail pass because of my mother-in-law who was in her late 80s.
Many thanks,
Jim