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2 weeks + in Italy - Starting in Milan

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We will fly either from Tampa or Orlando to Milan - roundtrip - we hope to fly Delta as we are Silver Medallian members - and would prefer Premium Economy which Delta doesn't really have - airline suggestions welcome and thoughts on flying economy..
also not sure which airport in Milan is more desirable - We will meet 4 other friends in Milan.

Thinking of renting a van to travel around Italy or should we use train system?
This is a very rough draft of our itinerary.

We plan to leave Milan for the Piedmont Area - Alba, Barbaresco, Barollo, etc 3 nights
Drive to Cinque Terre - 2 nights
Drive to Tuscany - need a suggestion for a place to settle to drive around Tuscany - 5 nights
We are being hosted in the Val D' Orcia area at several wineries

Drive to Rome with a stop in Orvieto - 4 nighs
Then either drive back to Milan or take a train to fly back home.

We were originally planning to stay 21 days and go to the Amalfi Coast but thinking that may be too much to try and see in one trip traveling with 6 people.

Would love any suggestions on our itinerary or method of travel. We are all novices about Italy and ages 66-74 but all in good physical condition.

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