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First trip to Italy questions

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Hello all,

I have always appreciated the great advice I get from the Fodor's forums so I am hopeful that I can get some suggestions for our first trip to Italy.

Basic information about us: Good health, adventurous (but not adrenaline junkies), very interested in art, architecture, quiet nights, and good food. Total full days available: 12 (not counting arrival and departure dates). The budget is mid-range, about $200 per night hotel, leaving plenty left over for museums, etc. Travel in mid-October 2016.

Itinerary plans: Land in Rome, (5-6 days), train to Florence (3 days), rental car to drive through Tuscany back towards Rome, perhaps find a relaxing place to stay for a few days (suggestions)? Return car, stay one night in Rome before flying out.

I am hoping for recommendations for the following:

1. Is it worth the risk of bad weather to wait a few weeks and travel in November for cheaper prices? I don't want to save a few hundred only to be cold and rainy.

2. Flying from the east coast, I have many options such as Boston, NYC, Washington...any suggestions for the best airlines/flights? I definitely want premium economy.

3. Itinerary thoughts: We would like the restful part of the vacation to come at the end, hence the idea of a country villa in Tuscany. Does my Rome-Florence-Rome plan sound like the best idea? All suggestions welcome.

4. We want to maximize our time for as few stops (and unpacking) as possible, and are trying not to "stuff" the vacation with too many destinations but Rome and Florence are musts.

5. We prefer a VRBO type stay versus a hotel in both destinations, any recommendations are appreciated - in Rome, Camp di fiorni or Navano area.

Thanks for all and any help!

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