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Hi my fellow Italy lovers, Italians and world travelers,

I am traveling to Italy with my wife, mother and 1 year old daughter who walks like a champ already and has been traveling since she is 4 months, in mid September for 21 days. I wanted to share a rough Itinerary and wanted to get some suggestions on places to stay, eat and sights to see. Let me start of by saying we have been to Italy individually many times already and I even have some distant family in Viareggio. I am mentioning this because we are NOT first time tourists trying to pack all important sights into one trip. We are big time into food, wine, architecture and the Italian life in general. Ok here it goes and thanks for the feedback in advance.

Day 1: Arriving around lunch time in Rome (we are visiting family in Germany so this is the closest airport we can fly into and we really love Rome)We'll spend the rest of the day in Rome and we really enjoyed our stay at the Hotel San Anselmo (but open to other?) Nice dinner recommendation?
Day 2: Rome (not here to see the major sights just want to soak in the roman life, have some great lunch and dinner (love Trastevere!) I will check out the best 100 Gelato places and see whats good in Rome.
Day 3:We will now rent a big car and leave early morning and drive to the Tuscan countryside ideally in the Val d'Orcia, still looking for a great Agriturismo (Lupaia is sold out, Fontana would be amazing but it is just a little to far from where we want to be (closer to Montalcino) Why am I saying that? because ideally we use this place as a base to explore Tuscany especially the routes driving trough Valcd"Orcia and do day trips (Montelpulciano, Sienna and San Gimignano , Grosetto area Castiglione della Pescaia, 1 day we will 100% drive down to the Saturnia Thermal Baths as that was highly recommended for relaxing, open to other places) I just think its easier not to constantly unpack and with the kid and so if we want to relax one day at the pool or walk trough the vineyards, take on a cooking class, we can do that here. So that would mean 8 days in Tuscany countryside.
Day 11: early morning drive to Florence and basically do the same as in Rome, spend the rest of the day in Florence ( any recommendations for nice hotels and great food?) but not trying to pack all sights in as we have been to Florence before
Day 12: leave early morning and now this is the part of the trip we are not clear on at all; Originally our goal was to get to Reggio-Emilia/Parma/Modena because we love food. We wanted to do this by taking 2 days and driving trough Pisa/Viareggio (spend a night or 2) and get there via Cinque Terre which we have all never been to. Now my Italian friends are telling me it is not worth it and we should go from Florence to the Romagna area on the coast ( I think they referred to the Ravenna and the little coastal towns maybe?) and I believe the reason was it was so beautiful there and they have the best food. Then we should go to Verona and hang out on the Piazza della Erbe and explore Verona for the day and then instead of Modena we should go to Mantova (Mantua in English), and finally to Parma. Please share your thoughts on both options. Thank you.

Our end goal is to spend 5 days near Alba because by then it is truffle and wine seasons and there is a lot of nostalgic reasoning (many trips to Barolo area as a kid). Please suggest a nice Agriturismo and some restaurants. So that would mean Days 16-20 in Piemonte and then driving to Milan from where we will catch the flight.

Very much looking forward to your thoughts and suggestions!

Chris