Siena or Orvieto (1 day)

Both are well worth a visit but Siena hands down if you only get one. The Cathedral is one of the most impressive in Italy. Climbing the Torre Mangia a wonderful experience for a fabulous view. The Campo is arguably the most attractive town square and the Contradi are fun to wander searching out their totem fountains and symbols.

I am not a fan of Civita di Bagnareggio and can't imagine taking a child there. I visited on a Rick Steves tour and the walk from the bus parking lot to the causeway/bridge/walkway out to it was fairly long, then the walkway itself was a trek to get over to a crumbling village where almost no one lives any more. Most of the inhabitants seemed to be of the feline variety. Others love it, though.

I did Siena as a day trip and was able to stay 2 nights in Orvieto. They have a much different feel to me. Siena is bigger and seemed more touristed. I enjoyed Orvieto more. It is an uphill walk from the funicular station in Orvieto to the cathedral though.

OK, another view. Certainly both towns are wonderful, but here are a few reasons to choose Orvieto, assuming that you are correct and the time to drive to either city is the same: (1) your other experiences will be in Tuscany, Orvieto is in Umbria and will give you a chance to also experience that area. (2) my experience in Siena, echoed by others on this forum, was that when I arrived during the day I found Siena very crowded and not so special; it was only in the very late afternoon and evening, when the crowds of visitors and local workers thinned out and the lights illuminated the public buildings, that Siena turned magical; but it seems you will miss that if you want to be back to your lodging before dark; (3) there's a lot to see and do in Orvieto: an underground tour your daughter might like; also a beautiful Duomo with a gorgeous facade and the Signorelli Chapel inside, almost a smaller version of the Sistine Chapel, I believe I remember that it was an inspiration for Michelangelo; be sure to see and photograph the facade in the mid-to-late afternoon when the low sun is shining on it, just wonderful; also, there is a Duomo Museum with several buildings, I remember that in the building sort of a little behind the Duomo and to the right if you face the Duomo, there is a section where you are really eyeball-to-eyeball with some ancient mosaics and can really, really appreciate the intricate tile work; (4) lots of ancient little stone lanes with interesting craft shops, wine shops and restaurants, up near the Duomo; and (5) a visit to Civita would be interesting and different, if you can fit it into the day, even though no natives actually live in Civita anymore, the last elderly lady passed away a couple of years ago; however, it will take you about 30 minutes each way to drive Orvieto to Civita, then maybe 15 minutes each way to park and walk the pedestrian bridge to the town, and maybe an hour to walk through the town and have a cafe or gelato. The funicular is unusual and neat too, and I believe the funicular ticket includes a ride on the bus that goes from there uphill to the Piazza del Duomo. Happy choosing, there is no bad answer here!

Could you include a stop in Orvieto en route to Rome, if that is part of your larger plans?

Another vote for Orvieto. You could easily occupy a day or more there. In addition to the reasons specified by you and other responders, an advantage of visiting Orvieto with a young child is that it's pretty flat; I'm not sure I'd want to be hauling a three-year-old up and down the hills of Siena. And while you describe Siena has a larger city, I didn't find the modern part of the city particularly attractive or interesting – I didn't see it as a plus.

Also, I find the cathedral in Orvieto far more beautiful – both inside and outside. The major interior feature that I think about in the Siena Cathedral is the floor, but it's largely covered during most of the year. The Signorelli frescoes at Orvieto cathedral are stunning.

I've been to both, with Couchsurfing hosts each time.

I found Siena crowded, with tourists who seemed to be following the herd. I thought Orvieto was better - quieter, interesting things to stumble upon, and we crashed an art gallery party and made friends who invited us to dinner! So maybe my memories are tainted, but...... ;-) Orvieto was wonderful!

Enjoy!

Thank you everyone for the many replies and many compelling reasons for both towns
Just to clear up some questions
Civita I could do without, I was thinking it was close enough to make it worth taking a photo from the bridge if going to orvieto before or after. Not something required seemed like a nice photo opportunity only without having to drive too much further
I also thought it was another 15 minutes not 30 each way so may shelf that
Headed to San Marino after so don't have other opportunities to work them both in and all hotels are booked so cannot rework plans at this time
That said this decision could be a last minute one
If weather is inclimate would one be better for that?
If we are sick of crowds after cinque terre and elsewhere in Tuscany that may be a reason to choose Orvieto ; or of mobility issues are causing concern and delays with our daughter
On the other hand if we find less crowds than expected then Siena would likely be a better choice
One person's crowded could be quite different than another person's crowded

Chiming in late but I would suggest Orvieto for the Umbria connection. I love both cities, but I keep returning to Orvieto more often than to Siena. If you do go to Orvieto, go to the museum across the piazza from the façade of the Duomo. It's a nice museum, but for me the best part is the upper floor windows, which look out across the piazza to the mosaics on the Duomo façade, much closer view than you get from the ground in the piazza.

Something else I just thought of/ discovered

If opting for Siena it appears there is a decent option of giving the car a rest and taking the bus for this day trip
Given the amount of driving for much of this trip that could be a factor
Adds the hassle of a schedule and the bus times are not that frequent but an option that only works with Siena

I have been to both and I would chose Siena. The Duomo was amazing. In the month of September, they remove the floor coverings and expose the inlaid marble floors. I think it is one of the most beautiful churches I have seen.

Re bus to Siena -- this is an easy day trip from Florence. 2 or 3 buses travel there an hour; some are express and some stop a few times but even the non-express bus is a quick trip - about an hour. The bus leaves you at the edge of the historic center and you can note the return times on the schedule at the bus stop. We always note when the second to last bus leaves, so we don't risk missing the last one. But you can head back whenever you like. I would not drive if in Florence.

We have driven to Siena from a base in Tuscany and Siena itself is a big city (although the historic center you want to visit is tiny) so you drive through a bit of city before getting to your destination. There are parking garages ringing the old walls and signs directing you to parking. If you do that be sure to note your streets as you walk into the Campo from there as the place is basically round and it is fairly easy to lose track of your route and which parking garage to head to. We particularly note street names where we turn to head into the Campo. Not a bad idea to write them and a few landmarks down.

Have lunch on the Campo at one of the sidewalk cafes; food is not hideously expensive nor fabulous but is fine and it is just a lovely place. Climb the Torre Mangia: https://janettravels.wordpress.com/2011/09/18/climbing-the-torre-mangia-at-67/ If you can't handle that, you can get another bird's eye view of the town from the museum. You can walk out onto the old unfinished wall of the Cathedral for a great vantage point with just a few stairs. The Cathedral was to be enlarged to more than double its size during the middle ages but bad architecture and the plague intervened and there is this one chunk of unfinished wall that afford a nice view over the very picturesque town. With a 3 year old you won't want to make the Torre Mangia climb.

Thanks Jane.,
Just to confirm would not be doing this day trip from Florence (Pienza to Siena or Pienza to Orvieto)
Your day plan still works the same just wanted to avoid any confusion. Bus from Pienza is not as frequent as Florence but still offered.
I enjoyed reading your blog and great shots from the tower.
The hike up the tower looks fantastic and while I would do it, looks like too much for our young daughter.
I think there are other areas we could ascend easier even if the views are not as great and don't reach the same heights?

With many folks on each side of the fence, I think I will ultimately decide to let this be a last minute decision and let it be dictated by our general mood the day before (mainly to judge if I feel like I want a rest from driving ; my wife will not want to drive so I will be doing all of the driving)
My general thought is if I want a rest from driving would be best to take the bus and do the day in Siena
If I don't and fine with driving more, then leaning Orvieto
Even thought the entire trip is a surprise for her I may ask her to choose between the 2 towns if she has a preference after we get to Pienza.

As I noted, there is an easy birds eye view of Siena from the Cathedral wall ruin accessed through the Museum. While you would of course keep a close hand on a toddler, it could be done with one. Just a few stairs here and there.

Siena is my favorite town in Italy -- still remember that first jaw dropping entry to the Cathedral 30 years ago - and every time we have visited there have been medieval pageants of some sort -- selecting the Palio entries, a pilgrimage to honor St. Katharine, boys practicing flag tossing in the side streets. Love the place.

If you do go to Orvieto, be sure to do the underground tour.

Siena. One of my favorite cities in Italy. Nothing like it.

Two things!

1) you mention hotels are hard to come by -- have you tried AirBNB.com? VERY common in Europe - i've been using it for years, so have many friends. Give it a look!

2) and somewhat unrelated -- if anyone reading this is considering the Cinque Terre region in their travels be aware!! The government of Italy announced htis week a ticket system is being instituted. Articles in Wall Street Journal, NYTimes, The Guardian and more... this is big news!

Enjoy!

Susan in Ireland

Susan
Not sure your reply is toward me?
I have hotels booked and not worries about the ct issue until more is known

Right now all is rumor only so no need to scare anyone