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Italy, how to start, how to travel

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I have read a lot of postings, but still need help. I read 'trains are slow';' rental cars are OK outside of the big cities'; Maybe it is a combination of trains and cars (and planes?). We plan a trip (14-28 days?) next May/June (when do the schools let out?) and I am not sure where to start, nor how to travel. My wife and I (retired) enjoyed driving around (some highway, some back roads) the French Riviera, Monaco, Switzerland, but dumped the car when we arrived in Paris.
Any benefit to starting in the north and working south (flying in from the U.S.)? Venice, Tuscany, Italian Riviera, and Rome are our must sees; Reading the blogs makes me want to add hill towns, and the Amalfi coast. Then I saw the route from Palermo to Messina, which looked awfully inviting; Is it crazy to consider moving by car and train from Palermo thru Tuscany, to Venice? Also, we prefer a flexible agenda; will we have problems with same day reservations at 4* hotels this time of year?

Thanks for your help getting me started in the right direction.

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