stevelyon

For goodness sake don't do Pisa - in my opinion and experience it was a complete waste and such a let down.

kybourbon

This thread is from last Sept. and got topped by pearl1220.

ewhull

Consider Gargonza, a walled village/hotel near Monte san Savino (only if driving). Not far from Arezzo or Siena or any of the Chianti towns.

enzo64

I vote for Cortona, Pienza, Montalcino

Saraho

Thanks for more good ideas. We'll be in Italy in three months so it's time for me to make some more definite plans.

taconictraveler

I second the idea of the San Quirico area in the val d'Orcia. And then you can see the wonderful gardens of La Foce. Everything about those gardens and even the accommodations there, is just wonderful!