Please sign in to post.

Hill Towns to see between Florence /Siena and then Siena/Rome

We are planning on renting a car upon leaving Florence and driving to our next destination, an Agriturisimo just outside Siena. I know the drive direct from Florence to Siena is approx. 90 minutes, but I would like to take most of a day to do it (say 8 hours) and stop in two or three Hill towns on the way, including a stop for lunch. Which two (or three) would you recommend, knowing we'd be only a few hours in each place? After a day spent in Siena, we'd like to do the same driving from Siena to Rome, stopping in 2 or three towns along the way. Any and all locations would be new to us, never having been south of Florence before. Suggestions/itineraries /comments welcomed.
Thanks in advance for your help.

Posted by
1994 posts

If you can work in Orvieto on your way to Rome, it's a lovely town with a beautiful cathedral and Etruscan sites. It's also a beautiful town for wandering.

Posted by
10334 posts

What Agriturismo are you staying in? Do you plan to do any day trips from the there, or are you just staying one night there on your way from Florence to Rome? I agree with stopping in Orvieto on your way from Siena to Rome. As for Florence to Siena, it depends. You could go west and go to San Gimignano and Volterra, or you could go east and go through the Chianti region. You might look at a map and guide book and see what appeals to you the most.

Posted by
790 posts

I'd echo some of the same comments. From Florence, taking the s222 through Chianti is a good opportunity to see that part of Tuscany. San Gimiginano is a great place to visit; you might be pressed for time to stop in a bunch of Chianti towns AND San Gimignano in one day. South of Siena, if you're at all interested in wine, Montalcino and Montepulciano. Pienza is nearby, delightful too. And then there's Orvieto. And that's just scratching the surface of delightful Tuscan hilltowns to visit.

Posted by
527 posts

We drove from Florence and spent one night in each Rada in Chianta, Montalcino and Montepulciano (for us it was mostly about the wines) returning the car easily in Chiusi. We then took a quick train ride to Orvieto which was our favorite, a perfectly wonderful town. After two nights we took a short train ride to Rome.

Posted by
35 posts

thanks for all the suggestions. we are thinking of seeing san gimignano & volterra on the first leg (florence-siena), and pienza, montepulciano and if time permits orvieto on the second (siena/rome). is this doable? and good lunch/eating recommendations in any of those places? anything along the way worth detouring to see?
thanks in advance for your assistance. this board is a wonderful planning asset, as are the people who utilize it. Jim

Posted by
337 posts

My favorite hill town is Montepulciano. You could easily spend a day there. Pienza, Montepulciano, and Orivieto is a lot to pack into one day. Maybe choose the one that's closest to your route to Rome, and just spend the day in that town, soaking up everything. (Visit the grocery store!) If you're in Montepulciano during lunch or teatime, there is a cafe called Poliziano that has breathtaking views from the open terrace. The food is wonderful. We never had bad food in Tuscany!

Posted by
527 posts

Montalcino is tiny and we used it more as a base for all the wonderful Brunello wineries. Most visits are by appointment and private but Fattoria dei Barbi does a nice job, more California Napa Valley style. Staying a night in Orvieto and getting to Rome in the morning saves some hotel money. If you can watch Ricks shows you'll get a feel for the different towns.