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First Trip to Italy

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I would appreciate suggestions. I have a 2 week trip planned for October 2012. It MUST include Ascoli-Pisceno in Le Marche (my dad was born there). I was thinking Rome, a week in Umbria with day trips including one to Ascoli (is that feasible?), then Florence/Venice. Is a week in Umbria too long? I really want more than just a tourist view of Italy and do not want to be in a new hotel every day or two. Any suggestions would be greatly appreciated.

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