Ok. So my husband and I have a wonderful Italian getaway planned for our 20 anniversary. We have never been before and are planning to take the train from Florence to Siena as we have an overnight stay and winery tour scheduled there . The following morning we will have car/ driver to get us to Rome. We can take our time as our only plans for that day are to get from Siena to Rome. I would love some thoughts on possible stops along the way. We have looked at maybe doing Montepulciano and Orvieto. That looks reasonable on a map, but is there something else we should do instead? We also considered going to Tivoli ( it appears to be kind of on the way.) Any great suggestions on stops, food, etc would be appreciated.

You should take the bus from Florence to Siena if you are staying in the historic part of Siena. The bus drops you right at the edge. The train station is a distance away and you would have to get transport to the center. The bus is also faster if you take the rapid bus.

From Siena to Rome, I would head towards Pienza first. You can wander Pienza (it's very small/compact - can be easily done in 30 minutes), get some pics and cheese before heading to Montepulciano. Have lunch in Montepulciano, sample some wine (lots of wine shops) and head towards Orvieto if still have time. If you have the driver the entire day, I would visit Orvieto, tour the Duomo and do the underground tour before leaving for Rome. I think Tivoli is too far out of the way.

If San Gimignano is not part of your plans, it should be. I also agree strongly that Pienza is worth a visit.

Orvieto is fabulous. I would at least try to tour its Duomo with the amazing Signorelli fresco series. The underground tour (Etruscan layer of the city) is very interesting and the office is right on the Duomo piazza, but if you are short on time, I'd see the Duomo.

From Siena---and with a private driver---I would head south on S-2 and stop first in Montalcino for wine tasing and more.
Then, onward to Orvieto via a quick stop in Bagno Vignoni, and have the driver drop you at the train station to stow your luggage in Orvieto. Send the driver home at this point and save your self probably 150E---you can easily train into Rome from here and taxi to your hotel. Have fun !

Kybourbon- thanks for the heads up on the bus/ train. I didn't realize the train station was out of the way. We are both wine and cheese lovers. Can one exist on those two alone? Thank you. It sounds like excellent advice to stop in Pienza as well.

Ack islander- we would love to visit San Gimignano, but it looked like we would be back tracking north from Siena. Is that wrong?

Texasaggie- I thnk Orvieto is a must do on the way.

I understand there are a couple of Abbeys to visit as well. Not sure where those might fit in. Any thoughts on that?
Thanks for all of the advice. Your experience is invaluable.