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Help! 2 week Italy trip (South>Central>North)

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I am an American English teacher currently living in Verona, Italy and I am trying to plan a two week trip for my mother to come visit me. The goal of the trip is to see the south (Sicily) and central (Tuscany) for a week before finishing in the North, where I live, for a week. The rough draft of the trip is:

Begin in Catania for approximately 3 days.

Fly into Pisa and rent a car to stay in an agriturismo in Tuscany for approx 4 days.

Take the train to Verona and stay for one week with day trips to Venice and Garda.

I'm not worried about the North/Veneto, but I need help with the South/Central regions! Specifically info about:

- Catania airport and inexpensive places to stay (B&Bs, etc).
- Getting from Catania to Tuscany
- Where to stay in Tuscany to see countryside (have been recommended Chianti, Montepulcino, S. Gimignano, etc.) Looking for close to Pisa/Siena and beautiful, of course.
- Recommended car rental options (is it true that manual is that much cheaper than automatic?)

My mother is about 60 and we are looking to keep this as simple and nice as possible. The main goals are good food, good wine, beautiful scenery, and a nice time. We don't want to stress ourselves out with details but we do want to see some of the great parts of Italy (she has never been). I am trying to extensively plan now to keep it easy later.

Any info on the above topics would be HUGELY appreciated!!!

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