I'm having a difficult time narrowing down the location i'd like to spend a 2 day trip between Florence and Rome.

I'm leaning toward Siena as a very centrally located city

but i'm still considering the Chianti's - Radda or Castellina in Chianti.

I'm departing from Florence, so perhaps

Day 1 I spend a day in the Chianti towns and then head to Sienna to sleep.

Day 2 Tour Sienna and San Gimignano - head back to Sienna to sleep

Day 3 visit Montepulciano and Montalcino - then drive on to Rome

Is this too eager?

So Chianti or Sienna?