Northern Italy

You might want a car in Orsago if "root hunting" is on the agenda, even though Orsago does have a train station. Driving from there to Tuscany is certainly a possibility, just be sure to read up on the ins and outs of driving in Italy.

1. Autostrada has tolls, they can add up.
2. Speeding is enforced by robocams. You won't know you got a ticket until 6 months after you get home and your credit card is charged the equivalent of 50 EUR by the rental agency. That is just their fee for giving the authorities your contact information. The actual ticket arrives 6 months later by registered mail.
3. ZTL's, forbidden zones in central cities where you must have a permit to enter, again enforced by robocams and the result is the same as the speeding tickets.

Just be forewarned. Hate to see you post back a year from now screaming "Scam! Ripoff!" The clueless have racked up as many a dozen tickets on their Italian vacations. The bridge from the mainland to Venice is famous. People get 2 tickets when they drive across, triggering the camera on both ends for exceeding the limit by 5 kph. The city of Florence sends unpaid ZTL violations to international collection agencies.

Oh, and get an International Drivers Permit to go with your license.

Two nights in quite a short visit to Venice. That gives you a bit less time in Venice than in Verona, and I'm totally discounting your arrival day in Verona since you're likely to be jetlagged and sleep-deprived.

Thank you Sam I have read the theory on driving in big cities in Italy and saw it’s in-depth road rules just thought if someone who has been there from a practical side could say it was doable without too much stress

Thanks acraven is venice worth the 3 nights and Verona 2?

Venice is without a doubt worth three nights. I think that's the bare minimum. I haven't been to Verona, so it would be foolish of me to comment about it.

Ok great acraven I’ll do some juggling
Apart from Tuscan region do you think travel by car or train. Thoughts??

I don't know Orsago at all, but trains are really convenient between the major cities and typically much, much faster than driving. Plus no parking issues and no risk of receiving the all-too-common traffic tickets in the mail 6 to 12 months later (plus administrative fees charged by the rental-car company for telling Italian law enforcement where to send the fines).

For bouncing between small towns in Tuscany, or elsewhere, a car is really advantageous. You have to weigh the hassles of picking on up and returning it (plus the traffic-ticket risk) against the time you will save (compared to buses) and the ability to see more of the countryside, faster. It's a question that's a lot easier to answer when you have a list of small towns you hope to see and know how many days you'll have to see them.