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Italy - Tour or Independent Travel

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I am trying to plan a June trip to Italy and would like to fly in to Rome and out of Milan visiting places in between - Siena, Pisa, Florence, Venice. The trip will be for me and my two kids who are in their late teens. A tour will be between $2,500 & $3,000 per person without airfare. Just wondering how this would compare to independent travel using trains to go between the various cities and probably renting a car out of Siena to do some exploring. Sort of like the idea of having things "taken care of" by a tour, but worry about being herded like cattle and possibly rushed. Would anyone recommend a private guide, in Rome for instance, if we go the independent route? I have never traveled outside of the US, so this will be a very new experience. I have enjoyed reading the other posts on this forum; they are very helpful.

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