Can anyone tell me how long a drive it is from Venice to Sienna?
About four hours.
Has anyone done this drive?
Is it an easy/pretty drive?
We drove from Florence to Venice (missed our train, long story) and thought it was easy, interesting. Basically all highway, but hey, highway in Italy! Sunflower groves, interesting architecture spotted along the way but also the usual industrial areas. I bet coming from the south (Sienna) through Chianti region would be more beautiful. We did not find it hard to drive at all from Rome to Adriatic coast, through Abruzzo, up to Florence and over to Lucca, Pisa, and finally Florence to Venice. Very easy car drop off in Venice and then walk, or boat to hotel. If we can do it, I know anyone can!! We like public transportation, but were so glad to have car in Italy for some of trip.
We drove from Venice to Florence (about 50 miles shy of your drive) last year and thought the drive was very scenic and the roads were easy to navigate. The only problem we had was getting stuck in rush hour traffic going through Bologna (which added a good 30 minutes to the trip), but I'd take rush hour in Bologna over Chicago anyday. Have fun!