5 nights, Siena or Orvieto? Or Both?

We will be there the last two weeks of March if that would have an effect on any responses.

To my mind, Orvieto is a bit far from the Montalcino-Montepulciano action. You can take a driving tour that direction and visit both towns plus the lovely Val d'Orcia, but it will be about 3.5 hours just for driving in that day. Chianti is even further and IMO not a day trip from Orvieto. Umbria, though is a great wine region and less on the radar of the average North American. We had a wonderful tour with Mark of Gusto Wine Tours, who will get you into some places you may not be able to get into yourselves. (FYI we went in December.) And from Orvieto you can visit so many towns: Perugia, Spello, Assisi, Spoleto. If you really love the agriturismo you found, why not stay in Umbria and skip Tuscany? Umbria is said to be like Tuscany was many years ago.

In March, the unpleasant tourism jam of Siena shouldn't be as awful as it is June-August. I would note that Orvieto is very, very attractive. As hinted in the last reply, no one will ask you if you went to Orvieto. They will ask you if you went to Siena! Downtown is downtown, but Siena is at least ten times bigger than Orvieto.

You need to use Google Maps to determine just how pastoral or urban your Agritourismos are. I wonder if the major wineries still want reservations in March or not. Wherever you stay, you will spend a lot of time in the car.

Edit: I was only reporting, not endorsing Siena. Because Siena and San G are both UNESCO WHS, we HAD to go. Both were noisy and jammed in the first week of July and I do not recommend either. Times Square NYC is pleasanter. We loved Orvieto, but maybe not to sleep in unless you don't have a car.

Thank you for these great responses!

It's funny, the first question a friend asked when I told her of our trip was, "Are you going to Siena?" :)

I will be the rare dissenter on Siena. It was "meh" for us. We preferred Orvieto. It is harder to find parking in Siena, although if you stay at an agriturismo that is less of an issue.

Definitely do both! 5 nights is adequate for both and too much for either one. I have been to both. I liked Siena, I feel in love with little Orvieto. There is more to see and do in Siena. Orvieto along with a day trip to Civita Di Bagnoregio is very relaxing and laid back. You can easily do 3 nights Siena (day trip by group tour bus to San Gimignano for afternoon wine) and 2 in Orvieto. Personally, I would do 2 nights Siena and 3 in Orvieto because of personal feelings and preferences. Please go for both!

I would recommend spending 3 nights in Siena and 2 nights in Orvieto. Both cities are great, but there is more to do in Siena so I would spend more time there.

Day 1 - To Orvieto (2nts)
Day 2 - Orvieto or Assisi
Day 3 - via Montalcino & Montepulciano to Siena (3nts)
Day 4 - Siena
Day 5 - Chianti or San Gimignano

Day 1 - To Orvieto (2nts)
Day 2 - Orvieto or Assisi
Day 3 - via Montalcino & Montepulciano to Siena (3nts)
Day 4 - Siena
Day 5 - Chianti or San Gimignano

I agree with the post above, Siena and the Montalcino/Montepulciano areas deserve a visit the drive between the two towns is simply spectacular you will enjoy the Val D'Orcia Valley. If you love wine the Capanna winery definitely worth a stop you can get award winning brunellos for 25€ per bottle. The winery is still family run and still do things by hand. You can also enjoy the tour and tasting there. http://www.capannamontalcino.com/

You have plenty of time to do both. I agree with the three nights in Siena and two nights in Orvieto. Are you leaving from Rome? If so, leave Orvieto for last as it is an easy ride to Rome.

Thank you so much for the responses, everyone! The consensus seems to be to split the nights between the two locations and I see why that would be the thing to do. It seems like the best way to easily see more of the countryside. So, I feel like that is what I should do. However, there is this little voice in my head that keeps saying "wouldn't it be nice to just stay in one place for 5 nights in a row? Take it easy, relax, like a vacation within a vacation". I guess we need to figure out what our priorities are.

I am with you on staying in one place for 5 nights. However, for me, it would have to be IN a town, not on the outskirts. We are renting an apartment in Orvieto for 4 nights. That's really only three days - so staying put the first day, renting a car and going to a cooking class nearby on the second day, and leaving the third day open to either wandering or staying put. If we stay put, we will probably rent bikes and pedal around the town. Staying in an agriturismo sounds lovely, but you are tied to the place for the evening, (assuming you drink), and you are forced to drive somewhere every day.

But to each his own! Have fun deciding!