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Assisi, Chianti & Inqie Terre-2 wks.

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We are just starting to plan a 2wk. trip to Italy (2017) in celebration of our 35th anniversary. The towns that we definitely want to visit are Assisi, the 5 Towns of Chianti (+Sienna & San Gimignano or others?) and Cinque Terre. We're looking for suggestions as to:

1. Which airports to fly in/out of in Italy? (Home airport is SF.)
2. In what sequence should we visit these towns? (One thought - Fly into Rome/train to Assisi, drive through Chianti/train to Cinque Terre/Train to Florence or Milan to Depart for Home.)
3. Best dates? (We would like to be in Chianti for the peak of grape picking/crush.)
4. Any suggestions for accommodations? (Could we stay in one location in Chianti as a home base to visit the other towns?)
5. Any suggestions for restaurants?
6. Any "must do/see" wineries, castles, churches, farms, abbeys, festivals, tours,etc.?

We don't expect anyone to answer all of our questions. But we're hoping to gather enough suggestions from multiple travelers to compile an itinerary.

Thank you for any contributions that anyone can make!
:)

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