4 nights in Tuscany

Touring Tuscany by car is a pretty laid back experience. It is a great place to slow down and smell the roses.

I'd suggest you just take your time getting to your agriturismo. After you're checked in, just drive around the countryside to get your bearings. We especially like to ramble from town to town in such a scenic place without making any plans.

The trip over to Volterra will take you by the hilltown of San Gimignano. Certaldo is maybe 5-6 miles north of San G, and it's another hilltown to visit.

To get from Siena to Montepulciano, you'd go on Raccordo-Siena-Bettole (4 lane) southeast to A1 Autostrada (Tollway) and go south a short distance to the Gli Stalloni-Fontana exit. Turn right and follow the signs to Montepulciano. It's an easy drive that way, and you could also visit Pienza in one day.

Hi Christine...David is so correct about touring Tuscany and the many wonderful hill towns. Montepulciano and Pienza are both towns not to miss and yes they can be done in the same day. We stayed near Lake Bolsena for 3 wks and we liked those two towns so much we visited them twice. He is also correct about smelling the roses. The topography is so stunning it is almost surreal. On the way to Montepulciano we explored several abandoned villas...probably not lawful...but really fun. If you can visit Assisi do so. Perugia is nice also but doing them both in one day would be exhausting for me. I think I would visit Orvieto instead.
Have a wonderful trip. Just relax and go.

Your itinerary makes sense. I suggest that you also include at least San Gimignano and Monteriggioni in your itinerary, and possibly Colle Val D'Elsa and Certaldo. They are all in the immediate vicinity in the Alta Val d'Elsa (Upper Elsa Valley).
In my numerous day trips to the Val d'Orcia, coming from Florence, I wouid often include Montepulciano, San Quirico, Pienza and Montalcino in one shot. So you will certainly have time for 2 of them.

Well, you haven't told us where the Agriturismo is exactly, but if it is north of Siena to go to Montepulciano I used to take the Via Cassia to San Quirico, then the road to Chianciano through Pienza. It's probably a little longer (in terms of time) to get to Montepulciano than going through Sinalunga, but that way you can hit San Quirico and Pienza on the way there and kill three nice towns along the way. Actually on the way to San Quirico, I would often do also a little detour to Montalcino for a few minutes to get my fix from the local "dealers" (I have an addiction to Brunello that in spite of numerous brunello cessation rehab programs I haven't been able to cure).

It is west of Siena- Agriturismo Marciano- afraid to mention the name out loud here!

I got the impression that San Gimignano would be more touristy than Volterra- so chose we Volterra over it.

Thought we would take route to Montepulciano that David mentioned hitting Montepulciano first then Pienza and head back to Siena going north on Via Cassa.

Fo the trip to the Abbey we would take the Crete Senese drive thru Asciano - would need to get to Abbey before it closes at 12- then poke around to the south- San Quirico, Bagno Vignoni, Montalcino, etc- want that to be a really low key day.

Just looking at map and trying to hit different routes/scenery each day.

We do have 2 nights in Assisi- so plenty of time there- Perugia hasn't really grabbed my interest as yet- but it is a possibility. If we skip we’d have Saturday to tour Assisi-then could drive around Umbria- Spello, Bevagna, on Sun- heading to Orvieto on Mon where we have 2 nights and might try to get to Todi and Civita Bagnoregio on the way.

Then train to Rome for final 5 days of trip.

Thanks for all advice- there is so much to see and do in the area it’s hard to work it all out- and I think I am overestimating how long to get from town to town or how long needed to spend in each little town!

Perugia is actually a pretty town and it is worth a few hours at least for a walk on Corso Vannucci all the way to the Duomo.
If you've never been to San Gimignano, you need to include it.
Going to Tuscany and not seeing S.Gimignano is like coming to NorCal and not visiting San Francisco.

Well you got me there Roberto!
I was born and raised in SF- although when I go "home" now we just drive right thru the city to Sonoma County where most of my family lives now-
My father told me the same thing about San Gimignano- so I will add it to our list ;)

Christine...Am so excited for you. One of my regrets is not visiting S.Gimignano. Roberto is certainly correct about that. Keep this in mind as you are driving around: Enjoy each spot and don't stress yourself out getting to the next one. Maybe you will just have to go back!

So glad you are going to Orvieto.

Civita de Bangnoregio was remarkable. You will never forget it. My 7 yr old grandson still talks about the place. It is breathtaking (literally and figuratively).

Spending those 5 days in Rome is an excellent idea. We did the same thing and it worked out well. Am saving to rent an apt. there for our next visit. Please post how your train use worked out. We did not use it but I would like to in the future.

I love and have stayed in Montepulciano twice for one week each. I loved to visit and eat in Montalcino, as well as Pienza. For your trip prep I would recommend A Vineyard in Tuscany by Ferenc Mate, whose vineyard is just outside of Montalcino. Sounds like a great trip.

I love and have stayed in Montepulciano twice for one week each. I loved to visit and eat in Montalcino, as well as Pienza. For your trip prep I would recommend A Vineyard in Tuscany by Ferenc Mate, whose vineyard is just outside of Montalcino. Sounds like a great trip. Enjoy and drive safely. You may find you want to spend more than one day strolling around Siena. Lots of experience there. We took a one day bus tour that included a wine tasting with soup and local sausage snacking, a visit to Castellina in Chianti, and San Gimignano. It was the only tour we ever took in Italy and it was great and saved us from driving everywhere. We booked in the tourist office on the Campo in Siena. Another little known or visited place to visit is the old section of Chiusi, near Montepulciano on the train line, with its Etruscan museum, Etruscan and Roman water tunnels (Porcenna's Labyrinth) and some of the best food and friendliest people we have ever met.