We are spending 3 nights in Rome and 5 nights in Florence, but have 2 nights before we get to Florence and would like to stay in the Tuscany area. I had a friend stay in Perugia and loved it. I am trying to decide if it is better to stay in Siena or rent a car for the couple of days before Florence and stay in Assisi or Perugia. Any suggestions on the best area to stay in. We will be going to Pisa from Florence so don't want to stay there. Appreciate any advice.
Both Assisi and Perugia are in Umbria, the region next to Tuscany. Either makes a good stopover, Perugia has better transportation connections.
Rent a car in Chiusi and visit Montepulciano and Pienza area, which would be far to visit from Florence by bus.
I agree with Roberto, rent a car and visit the hill towns of Tuscany. I would also recommend stay in an agriturismo. This would give you a nice mix of big city experience as well as the countryside, which is the point of Tuscany. Montalcino, Pienza, Montepulciano, Panzano etc are all wonderful hill towns to visit. If you go to tripadvisor and look up each of these towns and then got the the "other accommodations" you will get to see agriturismo reviews and pictures.