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Would like feedback on our planned Italy Itinerary please?

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We have five weeks to spend in Italy this September and I would really appreciate any comments from you seasoned travelers and experts on the following itinerary. All travel will be on trains or ferries. Since we are seniors schlepping luggage, we thought we would stay put in several centralized locations and take side trips. Here goes:

Arrive in Florence via overnight train from Paris on 8/25 and attend a cooking/language school in Montevarchi - Chianti (Toscana Mia) for the next five days.
On the 30th we are going to Cortona for 4 nights. While in Cortona, is it possible to day-trip to Assisi or other cities? (We have already been to Siena, Montepulciano, etc.)
The next stop is Sorrento - haven't made train reservations yet - what is the best, quickest way to get there?
We will be in Sorrento for 5 nights, during which time we plan to day-trip to Naples, Capri, Positano and Amalfi coast - but I'm wondering if we should do Ischia (just read the trip report here and it sounds great) - is that a day trip? Would it be worth while to spend a night on the Amalfi coast before heading south to Sicily - can we get to Sicily from there, or do we have to go back to Naples.
From Sorrento we are going to Taormina, with day trips to Palermo, etc. Should we take a train from Naples? or is a ferry better.
After 5 days in Sicily, we need to get back to Rome where we are staying for 5 days before going to Sardinia to sail. Again, what is the best and fastest way to get from Taormina to Rome. It's a long way. Overnight ferry?

Thanks so much for any input. I know it's a lot, (and believe, me I know how fortunate we are to be able to do this!!) But, hopefully it is not as complicated as I think. Taking trains will be a whole new experience for us.

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