We are traveling from Rome to Venice and have one night to plan in between. We will be there on July 3rd so I'm worried about Siena being a mess after Palio. Any suggestions? Something that will make it easy to continue on to Venice.
The "easiest" cities between Rome and Venice are Florence and Bologna.
If you want to stay in a quiet, quaint, small hilltown, then take a one hour train ride from Rome to Orvieto. Take the funicular from the train station up to the town. Stroll around the town and admire the architecture of the buildings, the beautiful facade and interior of the Duomo, and buy a bottle of Orvieto Classico. Read Rick Steves' Italy tour book to get more info on this charming town.
I would choose Verona or Bologna.
Ovieto will be much different from Rome. Peacefull and beautiful at night. I loved it. Bologna is about 1/2 or more between the 2 and is a great choice also. Both have differnt things to offer.
I absolutely love Orvieto, but it doesn't fit your criterion for being easy to continue on to Venice. From Orvieto you'll have to change trains in either Florence or Bologna. That said, it really is a great town. Here are some pictures from our trip to Orvieto in May 2011, in case you're interested. Happy travels.
Does anyone have any experience with Siena the day "after" Palio? Is it a mess? Should we avoid it? How hard is it to get to Venice from Siena?