We 2 older adults are visiting Siena in September for 9 days and want to visit some hill towns via bus or train. It appears that those under 2 hours from Siena, ordered by length of travel time, are Colle di Val D'Elsa (30 min.), Buonconvento (35 min. + optional 10 min. taxi to Monte Oliveto Maggiore), Castellina in Chianti (35 min.), Radda in Chianti (1 hr), and Montalcino via Buonconvento (each leg a 35 min. ride + wait time between train and bus). Pienze might also squeak onto the list. I haven't put San Gimignano (1-1.3 hrs) on the list because RS calls it a tourist trap, but the last bus back to Siena is 7:40 pm, so maybe I should reconsider. We'd rather not take taxis, but don't completely rule it out.
If you were going to advise us which three towns to visit this way which would it be? Why?
We like meandering in town, short walks (30-45 min.) in the country (especially with vistas), people watching, art, market browsing, eating, quirky local history, cooking, folk and classical music (but not opera)... and we're not into wine but want to sample the local specialties. We probably will take a guided tour or two from Siena to places inconvenient by public transit, e.g., Montepulciano.