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North from Tuscany, train or plane?

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Looking forward to input for some of our September planning, when we will be in the Cortona area of Tuscany for a week, then heading north to Switzerland. We leave our place in Tuscany on Saturday morning, Sept 19 and must be in Lausanne by Sunday evening for a 7am transfer to Basel Monday morning. We could probably go straight to Basel by late Sunday.
With such a brief window in mind, and that over a weekend, we welcome suggestions on how to do this. For example, can we take a train from Cortona, stop enroute somewhere (where??) for Saturday night and continue into Lausanne by Sunday evening? We would like the opportunity to see that area of northern Italy for the first time, vs flying over it. But perhaps it would be more ... practical as well as enjoyable to fly from Florence to Lausanne and invest a wee bit more time in Switzerland before catching a river cruise northward to Amsterdam? Or...?

Thank you for suggestions, and for your help. ��

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