Driving times

Viamichelin.com
Takes a bit to get used to how it is formatted, but is quite accurate, plus if you plug in car info you will get cost approximations for the trip.

Google maps will do this for you - simply choose a starting point and the click "Directions to". You can drag the resulting route to change it for options although that can sometimes give you strange results. You can also "Add Stop" for a third city along the way if you have a detour in mind.

You should take their drive times with a grain of salt - I'd add 10-20% for small, scenic roads like Tuscany and I'm not sure what "average speed" it uses for Italians on the freeway. But it is largely accurate and should give you a pretty good idea.

=Tod

Any website will do.

GoogleMaps, IMaps, Waze, ViaMichelin, etc.

I don't think one is better than the other and their estimates are comparable, give or take a few minutes up or down.

Just always add to the driving time the time it takes to find a parking place, figure out how to pay for parking, and then to walk (or sometimes also go by bus or elevator or funicular or whatever) to the part of town you are going to.