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Small town between Rome and Tirano

I just spontaneously bought an open jaw ticket RDU- Rome and CDG- RDU for last 2 weeks in April for amazing price of $625 on Iceland Air. After 2 nights in Rome would like to stay in a big village-small city that’s reachable by train where I can stay for 3-4 nights before I head to Tirano to catch the Bernina Express.
Only prerequisites are scenic locale, inland (not interested in coast although lakeside would work), some good restaurants in the town, and nice walking in area would be a bonus.
As a double bonus, the town or even region would have potential as a spot, perhaps a few years from now, for me to rent a small house or apartment for a 3-month period.
All ideas welcome, thank you!

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Your train journey to Tirano will start in Milan, so anyplace on, or close to, the train line between Roma and Milan would be easiest. Bologna is a major hub on that train line, ut is probably larger than you want. Nearby options would include Ferrara, Modena, and Parma.

We have not been to the latter two but really enjoyed a stay in Ferrara recently, in part because we loved this hotel:

https://www.annunziata.it/en/

It sits right on a little square across from the town castle, and adjacent to the main piazza and pedestrian zone in town. Lots of nice walking, including a long circuit around on the city walls.