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Itinerary plus car and train info . Please help!

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So, as posted earlier, we have a companion ticket that expires April 6th. The only time the airlines had for us was March 16-April 2, flying in and out of the same city, Rome. We have taken to heart in the past the suggestions of this board to not backtrack, but we had no choice this time. This is the plan so far, please give feedback, thoughts?!?

March 17th: arrive in Rome around 1pm. We are planning on taking the train that day from Rome to Florence. I know it will be a difficult day, but I just don't want to stay a few days in Rome and then at the end, spend a night again in Rome to catch our flight that leaves around 10am. Train recommendations? Fastest way? I understand tickets go on sale 120 days before? Is this correct?

Florence March 17, leaving March 22. I know that 5 days is a lot, but the first day will be a total waste with traveling & I know we will take it slow the next cause we will still be getting over jet lag. So, really only 3 days.

Rent a car on March 22nd from the airport since it's Sunday and many car rental outlets in town seem to be closed.

Now, the question…..who to rent from? In France, we rented from AutoEurope. I thought Kemwell was the same as AutoEurope, but their cars are different. We can get a diesel from Kemwell, but not AutoEurope. Any other suggestions?

March 22-March 25 Castellina staying at Fattoria Tregole. Explore the area, wine tasting, cooking class.

March 25-28 Pienza staying at Terre di Nano at house Casetta. I know these 2 areas are close together, but if you look at the pics of Casetta, I had to go there. Plus, I thought it would be nice to have our own kitchen and take things really slow in order to gear up for Rome. Thoughts?

Drive the 28th to Rome & drop car off at airport. Which one?

That's pretty much it. What am I not taking into consideration? Thanks for any help. I am so jealous when I read trip reports that have a month to spend! I hope to do that someday.

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