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Assistance Needed in Itinerary for Fall 2015

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We are going to fly in and out of Milan in late September/early October. I love a mixture of touring small towns and large cities. We will be spending 10 nights amongst a few towns/cities. Below are a couple of itineraries I have come up with. But I think I am being overly ambitious to include so many stops for 10 nights. We enjoy some time to relax as well.
Itinerary #1
Arrive in Milan
Go directly to Lake Como area for 2 nights
Travel to Turin for 2 nights
Travel to Nice for 2 nights
Travel to Florence for 2 nights
Travel to Milan for 2 nights
Then fly home

Itinerary #2
Arrive in Milan
Go directly to Turin, Italy
Then to Aix-en-Provence
Option #1 - drive up coast and then back to Milan for 1 or 2 nights
Option #2 After Aix-en-Provence to back Lake Como and finish trip in Milan

Suggestions on my itineraries please! Also would you drive or travel by train to all destinations. Once I get the itinerary finalized I'll be back to ask about suggested hotels but if you wish to provide those now for the cities I am considering visiting that would be great too! My price range on hotels is $100 - $150 with 3-4 stars. If my price point is way off let me know! Looking for any advice! Thanks all!

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