San Giminiano or Orvieto.... which would you pick?

I would choose Orvieto over San G as there were fewer tourists and, IMO, it was more interesting. It would be hard to dislike Orvieto and it is not that I dislike San G but I don't feel a need to return.

I think you will love Siena, especially in the evenings.

Both San Giminiano and Orvieto are well worth seeing. We visited both in October and we preferred San Giminiano -- it wasn't packed and Orvieto seemed rather abandoned. Judging from what the others say, it must be the difference in the time of year.

If you can only see one it seems you should pick a more classic hill town. I would probably pick San Gimignano. It's a classic medieval hill town with great towers. We really liked it.

The great thing about Orvieto is it's different than most other hill towns. It's on cliffs rather than a hill. It has a major cathedral plus tunnels under ground that date back to the Etruscans. We really liked Orvieto too.

I assume you are driving. San Gimignano is closer to Siena and would be a nice half-day excursion. For me, it was a lot more touristy with many pottery and souvenir shops. Having my guys with me and on a hot day, we didn't see much else. Orvieto was more quaint, with a few shops and an amazing Duomo. It is further from Siena, but as the previous poster said, it is a true hilltown. It really is a toss up.

Orvieto also has a nice underground tour of the tunnels under the city. If you buy the city pass, which is purchased in the tourist info shop right at the main parking lot at the base of the funicular, your transportation on the funicular and little shuttle bus up into town (be sure to take this rather than walk), plus the cost of the tour, is included in the pass. It's a good deal. Make sure to get to the tour office first so that you can sign up right away for the English tour (or maybe French?). The one we took I "think" was at either 11 or noon. There might have been another one around 2 or 3. I also recommend eating at the Rick Steves recommended restaurant, Trattoria del Moro Aronne Nidi! Lovely little place, delicious food, good service. BUT, San G is closer to you and maybe that will be nice. We elected not to go there because it sounded touristy. Still, I'm sure it is very nice.

We didn't like San Gimignano because it was just so absolutely touristy. Most all of the structures are in tip-top recently refurbished state...it almost looked brand new. All of the shops were just over priced tourist stores. You know, I really like to see authentic architecture and they way that the structures have weathered the centuries. San Gimignano is not like that at all.

San G is easier to get to from Siena, but has more day-trippers. It's less crowded in the early evening. Both towns are must-sees. The facade of the Orvieto Duomo literally takes your breath away. It is massive and just incredible.

It's so subjective. If you are the type of person who doesn't mind visiting a VERY touristy Italian town that almost feels like you are visiting Disney Land than maybe San G is for you. I personally did not like it for those reasons. I tend to prefer less touristy and seemingly more authentic sites when I visit Europe.

Hey, I just realized that you will be in Sienna ( I love it!), all hotels have brochures for day trips from Sienna. I think that the tour that I was on went to San G and Orvieto all in the same day. Plus a wine tasting. You really don't need to spend more than a hour or two at some of those cities and a guided tour is well worth it. It's a great deal.

Both in the same day! Brilliant! will check that option out for sure!!!

I have another idea just to really confuse things. Given 3 full days in Siena, I would spend 1 full day in Siena, 1 full day in Orvieto and your final day in Volterra/San Gimignano. They are fairly close in distance and I would spend most of the day in Volterra and then a few hours in San Gimignano at the end of the day. We visited both Volterra and San Gimignano in the same day last September and it worked out well. I found that a few hours was enough for me in San Gimi. I think San Gimi is a bit overrated and too touristy but I loved Volterra and there is a lot to see there. Hope I'm not throwing a wrench into your plans. Just food for thought. Have a great trip.