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Rome-Ancona-Florence in November: Train or Auto?

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This year's trip has a lot more challenges than those I've previously planned! I'm hoping for some recommendations or cautions to my work-in-progress.

-We will be four adults and a 2-year old, in Rome, over Thanksgiving: 6 nights
-After Rome, we will visit relatives, south of Ancona: 2 nights.
-Then, head west again, with Siena and Florence on the agenda: 5 nights.

I'm thinking we will fly into Rome, and depart from Florence or Pisa.
It's the 7 nights after leaving Rome, that are giving me problems:

a) We could take trains from Rome to Ancona; back to Florence; then day trip to Siena from Florence. (The 2-year old would be free, and some of the trains have "family" areas, with Legos and activities.) Would point-to-point trains be best, or a rail pass?

b) OR, we could rent a car leaving Rome, and drive to Marche; then spend a night or two in Siena and visit a hill town, or two; and drop the car upon arrival in Florence. This would give us more flexibility, but with 4 people and a car-seat, plus luggage, we'd need a full sized car, which could be more of a challenge to park, and navigate through narrow streets .

Anything, in particular, that I should be stressing about? I haven't checked the terrain across that area of Italy, but mountains and early snow would definitely be a vote against driving!

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