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First Trip to Italy-2 weeks

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We are planning our first trip to Italy for June 2017 (first 2 weeks) for our 25th anniv. Here is what our itinerary looks like so far (early planning):
Fly out of Montreal-Thursday night
Arrive in Rome-Friday morning
Saturday-Rome (realizing this is not much time)
Sunday- train from Rome to Pompeii then Sorrento?? (thinking this may be a good place to stay for 1 night?)
Monday-4 nights Positano (day trips to Amalfi, Ravello, Path of Gods, boating)
Friday-Head to Tuscany (Bucine Agriturismo)
6 nights Tuscany - (rent a car for day trips to small towns, relax, wine tours)
Thursday-Florence for 3 nights (2 days)
Sunday-fly out of Florence to Montreal

I realize the first half is pretty ambitious. Unsure if we should train or drive from Rome to Pompeii/Sorrento/Positano. DH is very comfortable driving and hotel has parking fairly reasonable. Have heard mixed reviews on driving Amalfi Coast. Thoughts?

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