San Gimignano or Orvieto?

In my opinion, Orvieto, hands down. It is far more interesting than San G. The duomo, both inside and out, is stunning. In a country filled with beautiful churches, this one stands out. There's a small museum with Etruscan finds also on the main piazza. We've not been there; but, I believe, there's a very old (Renaissance?) underground well system that can be visited. Plenty of atmospheric medieval streets, good restaurants, and yummy gelato - - the last being a very important consideration!

San Gimignano, hands down.
I'm Tuscan so I have to root for my region.
You can actually visit both as San Gimignano takes only a couple of hours to see. Orvieto half a day. Just leave early.

Orvieto, hands and feet down. (The well mentioned above is the Pozzo di San Patrizio, an engineering first and reminiscent of an Escher drawing.) The duomo facade is generally considered the most beautiful in Italy, which is definitely saying something. The chapel inside with the Signorelli fresco is jaw-dropping. Excellent food, stunning views from the walls and it's not as overrun by tourists as San Gim. Throw in the Etruscan museum and the underground labyrinth.
http://www.orvietounderground.it/index.php/en/

Thanks for that link Michael. The underground looks intriguing. Roberto, Tuscany vs Umbria eh?

Jim, I've visited and stayed a couple nights in each, and both are lovely. If forced to choose, I would pick Orvieto, a wonderful, ancient small city. The Duomo is magnificent, especially the facade when the sun shines directly on it late in the afternoon. Interesting museum just beside/behind the Duomo, where you can go eyeball-to-eyeball with some ancient mosaics. Also other interesting sites both above and below ground. Very nice shops, some excellent restaurants and wine. San Gimignano is smaller, more a hilltown than a small city, more heavily touristy and geared toward tourists, especially mid-morning to late-afternoon. It is easy to stay "on the beaten path" which is mostly one uphill street going up from the main gate up to the main square, the Piazza della Cisterna, with two great gelaterias, among other things. If you go further, beyond the beaten path, things are quieter, less touristy and more small town. I sent some friends an email from San Gimignano, and they responded "ah, the Manhattan of Tuscany!", referring to the skyline of many towers the town is known for, once 75 now down to 14 I believe. You really can't go wrong, just get an early start out of Rome, and enjoy the day!

Another vote for Orvieto - more to see and less packed with tourists.

Orvieto. Will this be a day stop or an overnight? Either way, your funivia ticket is also valid for the bus up to the Piazza del Duomo. I would not try to park in the upper town, but that's a personal choice.

Orvieto if only for the exterior of the cathedral. Don't forget the funicolare across the railway station to take you up to the town.
But if you should prefer San G., the under-visited San Agostino had nice frescoes in the apse.

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Orvieto is the vote by far. Not a overnight Zoe

Another Orvieto vote! I have been to both. I did the underground tour, Etruscan ruins. Very cool!

Put me in for Orvieto. It's right on the toll road north of Rome. We also like San Gimignano--for about an hour at 4:00 p.m. after all the tour buses have left.

eh, I can do both in one day. 4 hours in Ovieto and a couple in San Gimignano. Enough.

I'd also do both. I'd head to Orvieto early in the morning. Spend a few hours there and eat lunch there. Somtime in the afternoon head over to San G. Stay awhile and even have dinner in San. G. Then head out at night to Florence.

Yet another vote for Orvieto.

Of course both are great and worthwhile.
I think San Gimignano is perhaps a one trick pony - that being the towers.
Orvieto offers a more encompassing expreience.

Well I only visited Orvieto, spent so much time there, that not enough was left for San G. Loved it. Beautiful town, very few tourists. The Duomo Di Orvieto was incredible. Of course this being Italy in October, there was scaffolding all over the front ... bummer