Which Tuscan village?

Lucca is flat with a wonderful wall that is wide and has grassy areas; it's great for bicycling. Several shops rent bicycles. The town should be easy for your child, but can be crowded. In the CT, Monterosso is fairly flat compared to the other 4 towns and more walkable for short legs. There is a sandy beach there, too. Ferries to the other towns are available.

Will you have a car rental or rely on public transportation?

If Public Transportation I would stay in Siena as you have more buses to hill towns. Siena is a beautiful city to explore. There are direct buses to San Gimigano while you need a connection to reach Montalcino. I would also recomeend Tours by Roberto from Rick's book and tv show for a nice day in tuscany. I did a couple days with Roberto and the places we stopped were amazing.

If you will have a car I would say stay someplace between Siena and Pienza and you have easy access to Siena, Montalcino and also Monteplucliano in southern tuscany.

Try this for lodging, views and vino. http://www.collelungo.com/EN/index.html

They will direct you to some excellent wineries.

I would try to stay someplace other than Sienna with your car. Parking can be difficult. There are lots of other villages or agriturismos to stay in that would be easier with the car. I would definitely keep a car with a child... they don't always want to be on a train or bus schedule. The car might be an issue in CT... also difficult to park, etc. You could drop the car in LaSpezia and take the train for the rest of the trip.

Thank you so much for the feedback. We will rent a car when we leave Florence and have it until we get to the Malpensa airport.

After hearing about Lucca and looking at pics, I definitely want to do a day trip to Lucca. Since we have a car, and as suggested above, will probably stay 3 nights in montapulciano or pienza. Would that be too far? Hubby loves driving and kiddo is ok with car rides too.

Yes, monteresso it is for 5T given we have a car.

i am torn between how much time to spend in Tuscany (3 nights) and cinque Terre (2 nights). Need to definitely get back closer to MXP which is why we are spending the night at Stresa on the last night.

Should I leave it as is and probably get to Conque Terre early in the day (not stopping anywhere when we leave Tuscany), maybe even doing Pisa, Lucca and San Gimignano on one day while we stay in The Tuscan village.

I know it's rushed but not sure when we would be back :-)

Thoughts?

This is very rushed and you will spent so much time on logistics and so little time enjoying these places. I'd drop the CT and spend a couple more nights in Tuscany and would base in a hill town like Montpulciano at a hotel with parking

I would spend a long day in Lucca and if possible overnight (or 2) there. In addition to walking the walls, there are several park-like areas along the path where kiddo can run around a bit. Lots of people use the wall as a biking/walking/jogging path, or as a setting for a picnic. There are some great restaurants in Lucca as well.

Next on my list would be Montalcino or Arezzo, both are hill towns but Arezzo is quite a bit larger with more to do.