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Train Travel through Italy & Switzerland - Review This Itinerary?

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Traveling through Rome & Switzerland for the first time in early July. Putting the final touches on our train travel, and since this will be our first time, could really use some input on our train travel through Italy & Switzerland, as there seems to be quite a few quirks with the Italian train website..

- First major train trip is from Rome to Cinque de Terre. Plan is to leave Rome Termini via La Spezia to Monterosso. When I pull it up on the Trenitalia website for our July travel dates, it only provides an IC train option - this is because the full trip isn't bookable this far in advance, correct? But I should be able to book the Rome to La Spezia on the Frecca train right now, and then just purchase the regional train from La Spezia to Monterosso when we get there?

Here are the major legs of the trip:
Italy -
Rome to La Spezia - book now
La Spezia to Monteresso - regional, buy at station
Monterosso to Milan - IC, buy 30 days out
Milan to Tirano - regional, buy at station (30 min enough time to make the change in Milan?)
Tirano to Chur - Bernina Express, book now & reserve seats

Switzerland -
Chur to Lucerne - IR, book whenever, no advantage to pre-booking
Lucerne to Basel - IR, book whenever, no advantage to pre-booking
Basel to Paris - TGV, reserve now

How does this look? Any major flaws in the itinerary or understanding of the rules / best practices on either Italian or Swiss trains?

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