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FIRST ITALY (and Europe) Trip

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I posted an earlier post a few days ago about taking our (my wife and I) first Europe Trip: Paris - Venice - Florence - Rome. But we're moving more toward scrapping Paris (my wife is not super keen about that) and doing a 2 week Italy trip.
Our budget is around $3000 to $4000 (not including airfare), we would like to stay in hotels rather than hostels or dorms, we LOVE great authentic food and would like to visit all the main tourist spots (a few museums, and heritage sites, cultural stuff).

So, here are my questions for you :)

1. Your top 5 place to visit in Italy in order of importance if you had 2 full weeks (not including travel days)
2. Traveling to cities via train, car, or flight?
3. Affordable hotel recommendations?
4. Any tips/ideas?

Thanks!

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