Questions about Tuscany

Personally I don't think you can spend too much time in Tuscany. I've spent a total of 13 nights there over 3 trips and would still go back for more. However I will say that if this is your first time to Rome, you might be shortchanging it with only 3 nights. Just a personal observation.

I totally agree with Nancy. We have spent a total of nine nights in Rome over two trips and still haven't seen all we want to see. We are going back this May for four nights and I know that we will want to return again. Take maybe two nights off of Tuscany and add to Rome.

Just curious...are you staying at Villa di Sotto in Villa a Sesta? If so, are you taking your cooking class there? My daughter and I took their cooking class in March 2018 and had the best time! Paola, her husband, and daughter are lovely to work with.

Villa a Sesta has several excellent restaurants for such a tiny town. We always stay in an independent villa a few miles away from Villa a Sesta, but we always eat at least one dinner or lunch at Villa di Sotto...the food is excellent. Two other excellent restaurants there are Osteria alla Villa (very small restaurant with excellent food) and La Bottega del 30. L'Asinello Is also reputed to be excellent...for some reason, we have never eaten there but we may try it on our visit to the area this October.
I think your plans sound great, although I agree that 3 nights in Rome might be too short...maybe take a night away from the Val d’Orcia, although I love that area of southern Tuscany too. When we stay near Villa a Sesta for a week, we usually take a day trip to Florence, a day trip to Siena, a day trip to Pienza, and then visit other lovely nearby hillside towns.

We're spending 10 nights in Montichiello this Fall as well as 7 nights in Florence. Is "too much" even an option in this area?? Can't wait!!!

Other than the time in Florence, I see 8 nights in Tuscany. Florence is a city, albeit a small one. It is dense and highly art-centric. In 3 nights (2.5 days?) you will just scratch the surface.
One of the attractions of the rest of Tuscany is the large number of small towns, each with its own special attractions. The landscape is also extremely attractive. It wouldn’t be a bad plan to stay 4 nights in the north and 4 in the south. The distances appear small, but the roads are narrow, hilly and winding. Driving them gets old fast.

I think your length of stay in Venice is perfect. Without knowing what your goals for this trip are, it's hard to advise. Having said that, I think 3 nights for Roma is way too short. I would consider combining you time in Tuscany to one central location (perhaps in the vicinity of Sienna, perhaps at an agritourismo) for about 7 days. A rental car would be very helpful to visit the smaller towns, such as Montepulciano and Pienza.

I'm heading to Italy in 2 days, it will be my third trip, but first time with the whole family, so we are spending 3 nights in Roma and the rest at an agritourismo outside of Pienza (giving the kids a taste of both sides of the Italian experience).

I would increase a night to Rome. Also I don’t think I would bother to change accommodations in the Siena area. From Villa a Sesta to Montepulciano it’s only about 45-50 min drive. My daily one way commute is longer than that with traffic. Choose one place and stay put.

I agree that 3 nights in Rome is too short. It actually wasn’t in the original plan (I’ve been there before) but was added because we decided to fly home from there. I have considered adding a night there, but wasn’t sure if I should maybe drop one night in Montepulciano. Staying there was just to experience staying in a hill town.
Roberto and Todd, you both are suggesting one home base near Siena for all the days which I will definitely consider. I will say that the Siena area choice of base was between Raffaella’s del Chianti air BnB, which we are leaning toward, and Agriturismo Marciano which is closer to Siena as you probably know. It was a toss up. Thoughts?
Thank everyone for all your suggestions. It is very helpful.

Kathy, I was not familiar with Agriturismo Marciano, but after going to their website, it looks awesome, and walking distance to Sienna is a major plus. It's all about personal preferences, but if it were me, I'd go the agritourismo route.