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travel from Rome to Zurich over the Alps by train

We have 2 days at the end of a visit to Italy and want to travel by train through Swiss Alps and fly out of Zurich. We are considering the following: May 6 through 8, 2012 by train: Rome (via Milano) to Tirano in morning; arrive Tirano for late aft stroll, dinner, overnight stay (May 6) Tirano to Pontresina (or St Moritz?) via Berina Express: Morning train Lunch/Walk around Pontresina for a few hours Train to Zurich via Chur (afternoon-early eve) Stay in Zurich hotel close to airport (May 7) May 8: 1 pm flight home to Hawaii (23 hours) Sound do-able, enjoyable? alternate suggestions? Is Pontresina a good town to spend a few hours in? Leads on (moderately priced) places to stay in Tirano? Zurich? Is it necessary, recommended to make reservations on any/all of these trains in advance?
if this looks familiar, we got some good advice earlier, but had to shorten travel time. thoughts?

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