Siena

https://www.ricksteves.com/europe/italy/siena

Thank you for your response. I had checked this out previously. Wasn't sure if people on the forum had their own insight. Appreciate this though.

Your teenagers might enjoy Lorenzetti's Allegory of Good and Bad Government, perhaps after watching a video lecture about it that explains what the Latin labels on the various figures mean --- here's one video by Rocky Ruggiero: https://www.youtube.com/watch?v=kmX_i_u0FGY

They won't get to see the Palio, of course, but seeing a video of that makes the Campo even more interesting than it is. Here's Rocky again: https://www.youtube.com/watch?v=nq-WHl0VBPg

I've never done it (because 400 steps) but they could climb the Torre del Mangia for a great view of Siena.

The tower is well worth the effort it takes to climb it. The views from the top really help a visitor to appreciate the town and surrounding countryside. The added perspective (I think) helps to plan out where to go so I would do this early in the day.
If you take in the highlights, enjoy a nice lunch, have an espresso or gelato (both) one day is about right even without a hotel to retreat to.

Thanks! These are great ideas! I added to my list Basilica di Santa Maria dei Servi. I read that this was a beautiful view of the city; any first hand accounts? I also thought about tasking each kid to pick their "favorite" Contrade symbol and then walking to that district to take a picture of them with the flag and i believe maybe there is a fountain in each district that represents their symbol? Any idea if this is accurate? Thought it might be fun (if I didn't make it up : ) Again, thanks for your ideas!

Basilica di Santa Maria dei Servi is one of my favorite places. Yes, the city view is nice, but what I enjoy is that usually no one is ever there. It is very peaceful! As for the fountains I am not sure if every contrada has a fountain, but most do. They all have a museum, and some provide tours. If that is of interest the Civetta (Owl) contrada is a very good one to visit. I think your idea of having your teens locate the fountains (or the placques on the walls of the buildings that show the symbol for the contrada) is a great idea. You can buy a post-card or a small map of the city that will show the location of the various contrade.

The Facciatone is a decent climb (not as many steps as the Torre del Mangia) and has fabulous views. Very interesting climb too.

St. Catherine of Siena. Her head and thumb are on display at St. Dominic cathedral.

Thanks for all the info. I wonder if you can advise about something else. We plan to buy the tickets to the duomo complex, but wondered a few things. We have 2 days set aside for day trips from florence and wondered if the weather was yucky is Siena still a worthy visit? If we buy the tickets early, it gives us no flexibility to choose which day to go Siena. On the other hand, if we wait until we are in europe, tickets may be gone. Our other day is to go to Castiglioncello to go to the beach (this would be bad on a rainy day too) but we probably could just choose Siena over the beach, as we aren't buying train tickets until we are in Florence. The last time we were in florence it rained for 3 days, but in florence we just pushed through saw so much in the rain and then loved it on the 4th day when the sun came out : ) (this was long ago over thanksgiving). Wonder if Siena could be seen in the same way despite the rain? Any thoughts?

I would suggest taking a tour in Siena - if budget allows a private guide for 3 hours would be great.
They can give you a great overview, walk you around the city, etc . They can also take you in to a contrada museum for a real lesson about the Palio
If you get a guide, make sure they are from Siena!

You don't mention when you will be in Italy but it is often rainy from the Fall through the Spring but it does not typically rain all day. I would not let that get in the way of your sightseeing. Just push through and enjoy the beautiful town of Siena! BTW, you do not need to buy the tickets for the Duomo complex well in advance. You can usually buy them on the same day or wait until the day before you plan to go there.

Florence in the rain.....been there, done that. Sooooo dreary and with so many places requiring advance planning for access, not many good options to escape. Sienna is not as bad in lousy weather. There are enough things that you can do on the (relative) spur of the moment.

I too would suggest taking a tour in Siena. Look up Tours by Roberto. We had visited Siena on our own twice before we spent the day with Roberto. He was one of the best tour guides we have ever ever had.

Take the 151R bus there, drops you off in the top of town. Take the train back it runs much later than the bus.

So very helpful everyone. We plan to go early on the 131R and stay late. I do have another question that maybe someone may know. We are planning to also see a winery nearby midday and need to take a taxi there (apparently it is not a problem as it is only 10 minute drive). Has anyone gotten a taxi in Siena before? This is the only part of the day that has me a bit worried. If you have any advice, we would appreciate it. Thanks so much for all your wonderful guidance.

The nearest designated taxi stand near the Campo (historic center) is at Piazza Independenza. It is common to catch a taxi here for quick trips to the train station or elsewhere outside the city walls.

I’d check to see about the return taxi.

Such a big help to know that! I belive they will arrange a taxi for us, but will certainly check. Thanks so much!

Not to worry about finding a taxi in Siena. There are three main taxi "stands" that usually have taxis waiting for new customers. One is near the bus stop for the 131R bus. It is located in Piazza Matteotti, across the piazza from the post office. The other locations are Piazza Indipendenza and Piazza Duomo.

That is perfect! We will be at the Duomo in the morning and then catch a taxi for our adventure. Thanks everyone!

We visited Siena Sept 2022. We enjoyed walking around. The city has the well-defined neighborhoods.

We went to a specific restaurant, La Sosta di Violante, to have the Bistecca ala Firenze. Near it there is a small alley which leads uphill to Basilica di San Clemente. This has a fabulous view of the valley in the city. We saw young boys practicing the flag tossing ritual. We went to 6 PM mass, and were the only ones in the mass.