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Italy, Milan, Venice, Florence, Rome--frist time traveler needs help!

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Hello Everyone,
I have an opportunity to travel to Milan for 10 days with a friend third week of April. I would love any suggestions for day trips, may one or two night stays to perhaps Switzerland, Lake Como, any other suggestions. Someone mentioned Turin. Has anyone visited there recently. How would we get there (definitely don't want to drive). How much $ would traveling from Milan to these areas cost? What are sties we should definitely not miss while in Milan. Friend wants to see Last Supper, otherwise no other set plans. We're also trying to spend wisely and on a little bit of a tight budget.

Then DH will be meeting me in Italy for another two weeks. Would love to visit Rome, Venice, Florence and we need help with planning to make the best of our first visit to Italy. He would like to see Pompeii and we were thinking of skipping Pisa, should we? Any suggestions and tips are very much needed and appreciated. We like 4-5* hotels but to me as long as its clean, comfortable bed, safe and good location. Would it still be too cold to go the Amalfi Coast, Cinque Terre. I would like to get away to some romantic area and not so touristy for part of trip.

Also, any suggestions on planning where to met up as I would be traveling by myself via train I guess and then what city to start and end with return flight to Florida.

Thank you in advance. Ciao!

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