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Need help with travel logistics Tuscany to Alsace, etc

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We are just starting to plan our 2-3 wk trip for sometime in May of 2014.

Right now, the logistics of getting from point “A” to “B” and lodging in Pienza is where I need assistance.

We want to start in Rome (4-5 nights) and end up in Paris (4-5 nights.)
We’ve been to Rome but not Paris.

Two stops in between would tentatively be Pienza (3-4 nights to see that area by doing day trips).

We’ve been to Umbria, so Tuscany this time.

I chose Pienza because I’ve read that it is reasonably flat and easy to walk around. I’d like to find a hotel that has free parking at the hotel or very nearby that doesn’t require long walks back & forth just to park the car.
We would like to walk to different restaurants nearby for dinner each evening but not have to climb a hill to get there!
The hotel must have an elevator & A/C. Now that we’re older it is harder for us to navigate stairs (esp. w/luggage) and longer distances to walk.

We would probably take the bus from Rome to Siena and pick up a rental car there. Is that the best way?

Next area of interest is Alsace (3-4 nights)…not sure of the logistics of getting there from Tuscany…any suggestions?
Maybe drive to Florence, drop off car and fly or train to somewhere in Alsace and pick up another car maybe in Colmar or Strasbourgh?

Then the final step will be getting to Paris from Alsace. We could probably drop car & take a train or?

I would appreciate your input. You were all very helpful the last time I planned a trip. In fact, if it hadn’t been for your help, I would have canceled the entire trip!

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