My husband and I will be staying in an agriturismo near Montepulciano in May for 5 days. We are looking for the most scenic and beautiful Tuscany towns to visit. I hope to narrow our search!
The RS guide to Italy does a pretty good job of prioritizing Tuscan towns. Will you have a rental car, or are you looking to get around by public transportation? Do you want to visit the most famous towns, or do you prefer places your friends may not know about?
Plan a visit to the gardens at La Foce
https://janettravels.wordpress.com/2011/09/19/la-foce-in-the-heart-of-the-val-dorcia-2/
And a visit to Mont Oliveto Maggiore -- the abbey is lovely but the views on the way there are even lovelier.
Here are a few:
Pienza, Montalcino, San Quirico, Monticchiello, Siena, San Gimingano, Volterra, Monteriggioni, Florence, Arezzo, Cortona, Pisa, Lucca, Anghiari, Greve in Chianti
I thought countryside scenery wise the few mile area around San Quirico ; mostly in between Pienza/Monticchiello/San Quirico to be the best and most famous sites.