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Italy: Critique my Trip & Florence thoughts

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Headed to Italy September 19, 2012. This will be our third trip but we are bringing 3 couples: 1 is a veteran and 2 are newbies. Please critque trip.

Fly to Naples from US (2 veteran couples):
3 nights in Sorrento;
3 nights Rome; (the 2 newbies start their trip in Rome and stay 4 nights in Rome)
2 nights Florence;
4 nights Sienna (jumping off spot for Tuscan day trips);
2 nights Cinque Terra (yes we hav heard of flood damage);
2 nights Lake Orta
1 night Milan and fly out next morning

1) Comments?
2) Thoughts about where to stay in C.T. with this itinerary (we will have 2 cars & 3 couples at this point) and recent floods?
3) Thoughts about staying 6 nights in Sienna and just driving or taking bus to Florence? This was a comment on Trip Advisor.
4) Other recommendations?
5) Suggestions for hotel near Malpensa airport for early flights back to US?

Grazie

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