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19 Days/Night to spend in Italy - traveling by train

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Hi,

We are arriving in Frankfurt on Apr 24 and will be traveling by train (buying EuroRail pass) to Italy. We have about 19 days of vacation starting the 25th through May 13th 9allwoing Apr 24, May 14-15 for travel).

We have been to Rome and Venice on a previous trip and I am looking for suggestions on our itinerary. I am not sure of everything we will see and do at each place and am open to suggestions. We love to visit ruins, art museums, and enjoy good wine/food. We tend to walk a LOT on our trips and plan on fully using the local transportation and trains to get around. I was thinking of taking a cooking class in Southern Italy too as we love to cook!
Here is a list of the places we would like to go (probably too many)
Milan
Venice (loved Murano)
Florence
Pisa
Cinque Terre
Siena
Assisi
Rome
Naples
Pompeii
Sorrento
I am not sure if we can do all of this - I think we can if we do day trips.

Thanks in advance for any feedback/suggestions!

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