Decisions! Graduation trip with/for my foodie, history buff son for our first trip to Italy

For sure you will get the annoying crowds with summer heat in Florence and Siena;
so if it is some quiet slow time you want to experience, maybe daytrip to those towns from an Tuscan agritourism.
It is good to be tall; but if not, what kind of experience do you think you would get going to see a horse race hyped to the whole traveling world in Siena in the summer?

After 3 nights (do stay 3, BTW) in Venice, how about 5 nights in a Tuscan or Umbrian agriturismo? You'd have to rent a car, but you could take the train to a city near the agriturismo, rent a car there, tour, a return it before you take a train to Rome for your last 4 nights. The country experience of an agriturismo is right up a foodie's alley if you select one carefully. You can visit smaller towns during the days. Maybe take a cooking class at an agriturismo like Poggio Etrusco.

Me, I would love to go to the horse race! It is not just the race, but all the festivities leading up to it. You can stay in an agriturismo, and day trip to Siena. Even day trip to Florence if you want. Or rent a car and visit the countryside and small towns.

A second thought, being a foodie, he may like Bologna. It has it's history, is a university town, and the food in Emilia Romagna is different from other parts of Italy. From there, you can day trip to Parma, take food tours of The Parmagiano cheese, Parma ham, and Balsamic vinegar factories.

And, lastly, definitely stay in Venice 3 nights. Your first night you will be tired and jetlagged. Venice is best in early morning and later in the evening when the day trippers have gone.

Foodie = Bologna We loved our visit last September. We spent two days there...mostly eating.

Florence doesn't have to be crowded - select a location across the Arno away from the center and it can be quite pleasant.

I love the Lakes too but I think June and July could be crowded.

Siena - I love at night

How about some off the beaten path towns like Mantua or Chioggia - tourist there but mostly Italian tourist

Florence is fantastic, especially for a history buff. But off the beaten path, you might try Parma. My husband and I went and did a food tour, we were able to see parmiggiano cheese, prosciutto de Parma and balsamic vinegars were made. The old town was small and fun to explore and there was a nice art museum. Id love to go back!