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NEW TRIP Switzerland and North Italy--help in planning!

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Hi! My wife and I are planning a trip to Europe early October 2014. I am just beginning to plan it. I am not concerned with which hotels to stay in at this point, and I have done a lot of travel in the past. My main concern right now is planning and coordinating travel between points. Please supply what help you can. Budget is not a big issue, we want to use trains as much as possible (other than flying in from Charlotte of course!).
We want to take the Bernina Express and start in Switzerland (Zurich?) and fly out of Italy (Florence?).
Although I have been to Italy, my wife has not so we are not interested this time in villas, staying in the countryside, etc. This is largely a tourist trip. Maybe next time...
We want to go to Cinque Terre.
We want to go to Florence.
We have 10-12 days.

So the Bernina Express goes out of Chur and into Tirano. Fly into Zurich and take a train to Chur? Is Zurich worth a night--assuming we will arrive in the morning? Is Chur? I know nothing about Chur and Tirano. Would we be better off spending a night in Chur or Tirano or both? Can we stop in St. Moritz on the way or is it a true Express? Is a night in St. Moritz worth it?

How to get from Tirano to Cinque Terre?
And from Cinque Terre to Florence?

This is the backbone of the trip. Any suggestions helping to connect these spots and fleshing the trip out would be greatly appreciated! Or pertinent suggestions about alternatives, within reason. But the Express, Cinque Terre, and Florence are not changable. Thanks!!!!!!

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