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very confused. HELP!

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I'm planning out trip to Italy in June.
We're staying in Rome for 5 days. From there we wanT to go to Assisi and travel the Tuscan region. For me it's very confusing to plan this part!!!! WHERE DO I START??? If I leave from Assisi, where do I go FIRST??? Shall I choose one place in the "middle" of the region and travel to the other towns from there??? I want to go to cinque terre too, may be that would be my last destination.
Do you recommend DRIVING from town to town in the Tuscan region or going in tours??
(I want this trip not to be stressul for mu husband)
PLEASE HELP!

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