We are staying in Castellina in Chianti for a few days and have a pretty full calendar during our time there. We do have an afternoon that is still free and thinking of a short car ride to some other town in Tuscany to walk around and enjoy and would like your recommendations from the following spots we have interest in: San Gimignano Poggibonsi Monteriggioni or another of your choice thanks in advance,
Stop in Pistoia for NO tourists.
Cetaldo Alto, charming hill town not too far from you. google for photos and info.
I loved Montalcino, Montepulciano and Pienza...Edit: We saw very few, if any, tourists in these towns in July '08.
I really liked San Gimignano because it's so medieval, expect a lot of tourists year-round.
I loved San Gimignano, but stayed there 2 nights so got to enjoy the local feel when most tourists left. I also found Pienze beautiful. I'm not sure what there is to do in Monteriggioni because we didn't have enough time to go into the town, but the walls look amazing. Not in Tuscany strictly speaking, but close enough is Orvieto which is on a hill. The piazza by the Duomo is a lovely place to sit and have a glass of wine.
Panzano, 15 to 20 minutes away. Eat at Dario's meat market, either the lunch, or pick from one of the dinner options. A meat lovers heaven that will provide you with stories to regale your frinds with for years to come!
Panzano and Greve. You can do both in the afternoon from Castellina in Chianti. Have lunch in either.
We always love San Gimignano and have found it to be quieter in the afternoons. Monteriggioni is a charming pocket-sized hill town that is well preserved and has a couple of good restaurants. We were there once when the town having a festival, which was fun, but usually it is quiet and worth a stop.
On a recent RS Village Italy tour, we visited both Certaldo and Monteriggioni. Certaldo has an overlook of San Gimignano, so you might be able to do a little at both places. We were there for 1 - 2 hours. We also stopped at Monteriggioni for about 1 hour 15 min. Most people on tour I believe (including myself) felt that this was a little too long in this particular town. You can climb the wall but it isn't "complete" around. That is, you climb up the stairs and can walk to the left or right for 20- 30 feet, then you walk back down the stairs. Then, you can go to another section of the wall and do the same thing. I do think there was a small museum there that some tour members enjoyed but I didn't go there. Hope this helps. :) By the way our tour stayed in Castellina in Chianti at the Hotel Belvedere/San Leonino. If you're staying there, you will LOVE it. Try their eggplant parmesan. Yum!