Montepulciano to San Gimignano
 

I’m traveling around Tuscany from Aug. 13-17 and I need help finding the easiest way from Montepulciano to San Gimignano for two people. I’m assuming it is by bus, since we will not have a car. I find the sita bus website confusing when trying to look at schedules and time tables. Can anyone who is experienced traveling this area be of assistance?

It's not easy by bus. You would have to bus to Chianciano/Chiusi, catch a train to Siena or Florence, then a bus to San G (will have probably have to change buses in Poggibonsi). Another option, is to try to bus from Montepulciano to Siena (bus 112 I think) and then catch the bus to San G (might require a change in Poggibonsi too). Don't attempt this on a Sunday as there is little to no bus connections.

It seems you have a choice of taking the 112 or the 139 bus to Siena. I would choose whichever has the convenient time. From Siena you would switch to the 130. Here's the bus map. You may have to zoom in a few times to see these.

http://www.sienamobilita.it/mappe/Mappa_EXT.pdf

Some of the buses will depart from the auto station in Montepulciano (at the base of the hill town) although there may a be a pickup somewhere up in the hill town, but most depart from the station. You will have to check at the tourist office to see about other possible stops at the top. You can buy tickets at the station.

You may be dropped at the train station in Siena so you may have to ask about that also as the 130 may depart from Piazza Gramsci instead of the train station. If so, you can get there from the train station by exiting out front, crossing towards the mall where you will find steps outside going underground to the parking garage(there was a big remodel going on here last year so there may be an underground passage open now). You go down in the mall parking a couple of levels and the local bus to Siena's Piazza Gramsci (a big bus hub) runs through there. You can buy a ticket for the local bus underground from a machine (1€) or there was a ticket machine in the Siena train station where you exit to the outside. There are other ticket machines (one going into the bar), but they are not the machines you want. You may be able to buy a ticket also from the souvenier shop or the bar. There is an elevator down to the bus area if you don't want to drag luggage down the stairs (look for a place to go inside near the stairs and you will find it).

If you weren't able to buy your ticket for the 130 in Montepulciano in advance, you can buy it at Piazza Gramsci. It's underground also.

Is Montepulciano the closest place you'll stay to San Gim?

Here's the timetables, but you will need to check they are accurate after arrival as they don't always keep the websites up to date.
http://www.trainspa.it/train04/extraurbano.pdf

If you take the 112R, make sure you choose one that goes at least to Siena FS which is the train station (ditto the 139R). IMO, the 112 will be a more scenic ride.

You will notice on the 130A, some only go to Poggibonsi. I would choose one that goes all the way to San G. You'll notice these pick up at via Tozzi (Piazza Gramsci bus hub is on via Tozzi). There are lots of stores around the Piazza so you can grab some snacks/drinks. You should be able to buy your ticket at one of them also without going underground. If you want to visit Siena for a few hours enroute, the historic center is a couple of minutes walk from Piazza Gramsci. There is luggage storage underground (check hours and last bus to San G.)

Pay attention to the symbols at the top.
Crossed hammers (work days - Mon-Sat)
Cross (Sunday)
Circled A (weekdays except Sat)
SAB (Saturday only)
Estivo (summer)
Invernale (winter)

This was extremely informative. Thank you so much for this detailed response.