First things first:

Please tell your daughter-in-law that many cheeses in that part of Tuscany are not pasteurized and should not be eaten by pregnant women. The word for cheese in Italian is "formaggio" and the word for no is NO (or "senza" which means without). It will be easier if she just doesn't eat cheese at all than if she tries to figure out which are safe and which are not. If no one in the party speaks Italian, it can be good to find someone who does who can write out for your daughter-in-law a card in Italian that can be handed to waiters saying that she cannot eat any cheese at all.

For the itinerary, I suggest that they consider extending their stay in Florence to visit Pisa and Arezzo by train from Florence. It will be much easier to visit these places by train and there will be no need to keep switching hotels. Save the car for scenic driving, not visiting big cities with lots of traffic and rules that are hard for non-Italians to figure out.

If they pick one location just south of Siena, they should be able to visit Siena, San Gimignano,& Volterra, and Montepulciano from that one location. Because your daughter-in-law will be 5 months pregnant, she might appreciate staying either on a farm or in the flat town of Buonconvento rather than in a hilltown (they can be very steep). From Florence, they can take a scenic drive through the Chianti to their lodgings south of Siena.


From just south of Siena, it is easy to drive to see Civita di Bagnoregio and then drive to Orvieto to drop off the car there and take a train to Rome, which is the easier than trying to drive to Rome.

I would recommend that they skip Cortona because it is quite like many of the other places they are visiting, but very crowded with tourists.

So I would say add time to Florence, and then spend 5 nights just south of Siena, and drop off the car in Orvieto.

These seems to be in all directions so staying in two locations really doesn't work well.

How many days do they have in Florence? What is their budget?

here are farms and villas around Buonconvento

http://www.tripadvisor.com/Hotels-g635876-c3-Buonconvento_Tuscany-Hotels.html

http://www.tripadvisor.com/VacationRentals-g635876-Reviews-Buonconvento_Tuscany-Vacation_Rentals.html

http://www.tripadvisor.com/Hotels-g635876-Buonconvento_Tuscany-Hotels.html

valtor

My apologies: I read too fast and though you wrote that your daughter-in-law was 5 months pregnant, not with a 5-months infant!

So sorry! She can eat all the cheese she likes.

But otherwise, I stick with my advice.

Add a few days in Florence (rent an apartment there with the baby). Then take the train one day to Pisa, and then on another day to Arezzo.

Then rent someplace near Buonconvento. Near Asciano is also a good location for traveling to San Gimignano, Volterra and Montepuliciano.

See Civita d'Bagnoregio before going to lunch in Orvieto. After lunch, drop off the rental car and take your luggage to the train station and go to Rome that way.

If they really want to see Cortona, then go from the villa to Cortona for lunch, see Civita d'Bagnoregio and Orvieto after lunch, and then drop off the car before taking the train. (But I would skip Cortona.)

Thanks for the advices.

My DIL speaks Italian (her father is born in Italy). They visited Florence in the past, now they will be there for 4 days (before starting the visit from there to Rome- about I asked her)e, because there is a family reunion and it is organised by an aunt of DIL, living in Florence.
After this reunion is finished, they will start their trip and about this I asked for your help.

I am not sure about traveling by train, they think that with a small child it will be easier by car.

Thanks for suggestions; please keep them coming!

If they pick up a car in Florence and head directly to Pisa to see the tower, then drive to a place somewhere near Certaldo, then from that place they will have less than a one hour drive to San Gimignano, Volterra and Siena.

If they then relocate to the hills near Cortona, than it is less than a hour's drive to Arezzo, Orvieto and Montepulciano but if they run into traffic it will be more than a hour.

They can see Civita di Bagnoregio before dropping off the car, either in Orvieto (my recommendation) or in Rome.

But just to be clear: I am not suggesting that they travel by train with luggage to Arezzo or Pisa. I was suggesting that they if they are willing to stay 2 extra nights in a hotel in Florence, and take the 5-month old baby for a train ride to Pisa and back, and take the baby for a train ride to Arezzo and back, then they will not need to move twice with all their luggage and the baby while they are in the Tuscan countryside. They can stay in one place for 6 days near Asciano or Buonconvento and see everything.

I'm not pushing one or idea or the other. Just want to make sure you understand my previous suggestion.