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Where to be on my birthday...Florence or hilltown...itinerary help!

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My DH & I are planning our first trip to Italy for October 2011. Our first trip will consist of Cinque Terre, Florence & Tuscan hilltowns. I need some advice/opinions/suggestions on how to arrange my itinerary.

*OPTION 1:
Thursday September 29- fly to Italy from Austin, TX
Friday September 30- arrive in Pisa, Italy; take train to Cinque Terre (La Mala in Vernazza to be exact) and I'm counting this as <Cinque Terre DAY 1>
Saturday October 1- Cinque Terre DAY 2
Sunday October 2- Cinque Terre DAY 3
Monday October 3- train to Florence and I'm counting this as <Florence DAY 1>
Tuesday October 4- Florence DAY 2 & my birthday!
Wednesday October 5- Florence DAY 3
Thursday October 6- rental car to Montepulciano (Locanda San Francesco)
Friday October 7- Tuscan hilltown
Saturday October 8- Tuscan hilltown
Sunday October 9-Tuscan hilltown
Monday October 10- fly home

*Between option one & two the change will be flipping Florence & Tuscan hilltowns

*OPTION 2:
Thursday September 29- fly to Italy from Austin, TX
Friday September 30- arrive in Pisa, Italy; take the train to Cinque Terre and this will be <Cinque Terre DAY 1>
Saturday October 1- Cinque Terre DAY 2
Sunday October 2- Cinque Terre DAY 3
Monday October 3- train to Pisa; pickup rental car then drive to Montepulciano
Tuesday October 4- Tuscan hilltown & my birthday
Wednesday October 5- Tuscan hilltown
Thursday October 6- Tuscan hilltown
Friday October 7- drive to Florence; return rental car; Florence DAY 1
Saturday October 8- Florence DAY 2
Sunday October 9- Florence DAY 3
Monday October 10- fly home

*QUESTIONS:
1) If we choose option 2, what will the drive be like from Pisa to Montepulciano?
Such as: distance, driving in Tuscany & is it too much.
2) If it were your trip, would you rather be in Florence or a Tuscan hilltown for your birthday?
3) Which itinerary seems to flow more smoothly?
4) Will it be a lot more expensive to pick up a rental car in Pisa and return to Florence?

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