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Ideas for 3 weeks in Italy

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We know almost nothing about Italy but are just beginning to explore in preparation for a trip next year (spring 2016), so we'll start with asking you.

Our travelling style / interests:

On 4 past trips to EU (UK, Germany, Switzerland, Alsace-Loraine) we tended to go to lots of places, staying 3 or more nights in each, driving between them, split between magnet cities and small country towns. Interests: art, architecture, history, meeting people, and observing the culture of every-day life. The 3 of us are in our early 70's ... 2 of us are very active (ski, hike, walk a lot), one a bit less so.

This trip:

3 weeks. We're beginning to consider plopping down in 3 places and staying about a week in each and doing day trips from them -- perhaps we'd spend one or two nights at another location between the 3 bases.

Questions (yup, they're intentionally open-ended):

1. What 3 places would you recommend as 1-week bases?
2. I'm used to driving a lot (including in EU) ... we're debating on this trip whether to drive or use the train. In the places you recommend, would it be possible to easily do side trips by train, or would driving be more useful?
3. What months would you recommend?

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