We are headed to Tuscany in September. We plan to stay in Siena and then tour all the neighboring towns for 6 nights. We have been playing with the idea of staying near Pienza or Montepulciano for 2 nights. Should we?

We stayed in the town of Trequanda which is between Siena and Pienza and found it to be a most convenient location. Let me know if you want information on a place to stay.

I was in Tuscany cycling last Spet-Oct 2004. It is very easy to take the bus from Siena to any of the nearby small towns and the scenery is beautiful. I enjoyed the bus travel in Tuscany more than the train travel. Remember to buy your ticket at the tobacco store across from the square where the buses depart in Siena. Sometimes the schedules are a bit delayed, don't panic. I stayed in Siena and day tripped to San Gimignano. I think 3 nights in Siena is enough, so I would recommend staying elsewhere for your other 3 nights, or splitting 2/2/2 - remember traveling between the towns is easy.

Which other towns did you bus to from Siena, mountaincyclist?

Tad, with a car I would split it 3-3 and stay rural in south Tuscany. Look at www.letraverse.it near Pienza.