Help needed in planning and insight on driving in Italy.

Cinque Terra, Florence, Tucany, Sienna and Venice

and

9 days

5 places (counting "Tuscany" as a singularity, which it isn't). 9 days. Hmmm. You're probably not flying in to Cinque Terre, so it's probably 6 places. Do the math.

To put it bluntly: you don't have enough days for all the places you want to visit - whether you drive, take the train or a private helicopter. Each time you pick up and move to a new place, that consumes most or all of a day - more time than you think. So 6-places-in-9-days trip leaves you with not a single place where you actually have an entire day there.

Driving in Italy can be a delight (in the countryside), it can also be a nightmare (in the center of old cities and towns). But that's a secondary concern. Biggest issue I see is you have twice as many places as you have time for.

Picking a central location as a base for day trips would certainly help. But then you spend twice as much time driving (going someplace, then going back), and it's not like you have extra time to burn.

Depending what you mean by 'Tuscany", all the places you list are probably better without a car.

Just how many places are you trying to get to in 9 days ( nights?)

For the time you have, a car would be of no use. For the CT, Florence, Sienna, and Venice, that leaves no more than 2 nights per, not including Tuscany(well Florence and Sienna are Tuscany). Added to that, in the CT, Florence, and Venice; a car is a liability. At the very most, maybe you can find a place outside of Florence to rent a car for a day, or two, to explore Tuscany, but you likely will need to limit something else.

Do some research on ZTL's, that could cost you $100's if you drive, but you can easily fill your time without a car.

Here’s a start with the easiest logistics:

Day 1-2: Cinque Terre (not sure how you are starting here. Flying into Pisa?)
Day 3-7: Train to Florence. Day 4: take a day trip to Siena (easy by bus); Day 6: take a small group wine tour - many options from Florence.
Day 8-9: 2 hr. Train to Venice
Day 10: Fly home

Look at the RS Italy book regarding reservations at the major art museums in Florence, so you’re not wasting time in long lines.

Where are you flying into?
To get to the Cinque Terre, most would come in from the south changing to a slow local train at La Spezia. On the return, you'd usually go back to Florence most often through Pisa.
The best way to see Siena is by bus from the side of the Florence train station as the bus takes you into the city center in about an hour. It's a good day trip.
Depending on the time you have, you could possibly rent a car in Florence suburbs and head south to the hilltowns for a day.
If you're really short of time to see the region, the C/T would be the first place to eliminate from your itinerary.

Thanks for the responses. As you can tell I am just starting the planning process. What would you suggest for a 9 day stay between Florence, Venice with possible 2 night stay near Siena? Should I just stay in one 1 hotel and day trip to Siena? Also can anyone recommend a great cooking class, motorized bike tour? I aslo want to go to the stained glass place in Tuscany Rick Steves talks about but don't know the name. Thanks again for your input