Montalcino, Montepulciano, San Quirico or Monticchiello

Montalcino

I wouldn’t say they are all similar but they are all real towns
If only one I’d visit Montepulciano

If any are more geared to tourism that would be San Gimignano

Should we consider two separate day trips to the region?

You can make a loop from San Gimignano to Montalcino, San Quirico d’Orcia, Pienza, and Montepulciano then back to San Gimignano in less than 4 hours, not including stops and time spent in the towns. Expect beautiful views on the drive as well as from the towns. Maybe visit the Abbey of Sant’Antimo near Montalcino (closed midday so time it accordingly) and/or the Abbey of Monte Olivieto Maggiore which is between Montepulciano and San Gimignano.

What Laurel said

Thanks Laurel,

Part of the reason I am asking is that there are several stops I am hoping to make and our host suggested we break it up into two days.

Even then, her opinion was that San Quirico d’Orcia, Montepulciano, Montalcino and Monticchiello were all very similar and in order to not feel overly rushed, we should choose two of those four if we plan two day visits.

On one visit, I was thinking of leaving San G in the morning and visiting the following;

Cypresses of San Quirico d’Orcia
San Quirico d’Orcia
Cappella Madonna di Vitaleta
Pienza
Gladiator Avenue
Cypress Avenue Poggio Covili
The Abbey of Sant' Antimo
Montalcino

Then maybe plan a second day visiting Montalcino or Montepulciano ??

I wouldn’t miss Pienza, so add that one to the mix. Monticchiello can be visited in 20 minutes.
You can probably see all of them in one shot if you come from San Gimignano. It’s not that far.

SG itself is probably aimed more towards tourists than the other villages mentioned. We stayed in Montepulciano twice (which our celebrated advisor appears to have popularised) and visited most of your list. Two days is a more relaxed plan. Sticking to side roads will take longer but the driving is more enjoyable.

The villages are not overly similar and some may suprise you one way or the other. My top three visits would be Montepulciano, Pienza and Monte Olivetto Maggiore. We had lunch at the latter, before touring the abbey, grounds and wine cellar. About eight hours in Pienza, including a very long lunch, a couple of walkarounds, a beer in the aftenoon along the south wall, a walkaround the newer streets, watched an early evening amateur football game played on the lushest of fields.

Interesting aside. I think it was Livy who established that Spartacus lived at 221B Gladiator Avenue. During a different time, Commodus had a holiday cottage close by: as we all know, he wasn't very popular with his neighbours.