Full Tuscany tour


New member
Hello to everybody,
I am planning our next holiday for September 2014, in Tuscany region for 7 days.
We will rent a car from Florence.
I prepared my visit points, but I see that the list is very long and I could not decide how to divide my stays. We don’t prefer to stay in the same place and visit the villages in the surrounding and come back. I do not know whether if seven days will be enough to visit all these points, how much time to spend on each point?
My list is as:

Thanks in advance.


The Tuscan Expert ;-)
Staff member
Ciao Willy,

Yes, you definitely might be trying to see too much but once you're here, you'll be able to decide how much time to spend at each place and decide on the moment which you might be able to skip.

I've divided your list into possible days, as well as changing the order.... if you're planning on moving where you stay at night then it makes better sense to move at least in one direction with each day or grouping places which you can see from one place over the course of 2 days.

I also notice the MAJORITY of the places you want to visit are to the south of Siena, an area you can definitely visit over the course of several days from the same base.

Here are my tips:

Since you arrive in Florence, then you'll head south into Chianti and say keep moving south for the most part.

spend the night in Radda so that you can see RADDA IN CHIANTI in the evening/night.

Day 2 - I'd skip GAIOLE IN CHIANTI so that you can head down to SIENA and spend the rest of the day there. Overnight in Siena or nearby. So many people rush in Siena, but there is lots to see and soak in... definitely take the time to visit the Palazzo Comunale as well as the monuments around the Duomo.

Day 3 - head west out of Siena toward COLLE DI VAL D'ELSA (stopping along the way to see the very small medieval castle of MONTERIGGIONI) and then on to VOLTERRA (rest of the morning and lunch) and then SAN GIMIGIANO (pm). Spend the night in the area. Colle is small and you can do a quick walk and visit, but the other two do require spending more time in them.

Day 4 - Head south - the rest of your destinations are all in this area to the south of Siena, so you might consider finding a place to stay for the rest of the days. If you pick something central to reach by the end of this day (Buoncovento or San Quirico, for example, or the countryside anywhere in between), then you can use it as a base and depart in a different direction each day. Once you're here, consider it takes 11 minutes to reach Pienza, 12 to reach Bagno Vignoni, 18 to reach Montalcino (just to give you an idea of how close things are).

So I'd suggest heading toward MONTERONI D'ARBIA / ASCIANO / VAL D'ASSO / TREQUANDA / SAN GIOVANNI D'ASSO / CHIUSURE on this day as you head south.
I've actually not been to any of these yet myself so not sure how much time you really need to spend in each one, how much there is to see... I think you can skip Monteroni d'Arbia and head to Asciano and start from there.... you might not be able to stop at all the places on your list (some are also really small), but I have driven through and the landscapes getting there and in the area are really beautiful. In September, the harvest of most of the wheat will be over so you might get lots of pictures of plowed fields with the rolls of hay you often see in postcards - beautiful!

Day 5 - BUONCONVENTO / MONTALCINO / CASTELNUOVO DEL ABATE / CASTIGLIONE D'ORCIA (ROCCA D'ORCIA) - the places to stop and see are Buonconvento and Montalcino (stop at the Sant'Antimo abbey too) but this is more of a drive through wine country (and hills) than for stopping. We did this in the opposite direction and had lunch in Castiglione d'Orcia and there is a nice castle (closed as it isn't restored yet) and tower (the ROCCA in your list, private and cannot be visited) so you can stop and do a brief walk through the very small town but not see much. You are 20 minutes from San Quirico at that point, so if you stay there as suggested above, you can definitely do this as a day trip.

If you're not feeling for the drive, you could instead just stay near Montalcino and do wine tastings and a visit to a winery in the area and skip Castelnuovo and Castiglione, which you'll see from Bagno Vignoni).

Day 6 - You can head dedicate this day to the rest of the Val d'Orcia - BAGNO VIGNONI / SAN QUIRICO D'ORCIA / PIENZA / MONTICHIELLO - these are all worthy of stops and visits, so not sure whether you can really do all them in one day. They are all really close to each other, so see what you can see. Last day at your central base.

Day 7 - Of all the rest of the places on your list, I'd say head to MONTEPULCIANO and then on to AREZZO. Most of the rest are charming small villages, with a fortress or the remains of one in the center of the historical town. Most deserve visiting if you're staying in the area and you had more time. Unless you particularly want to visit LA FOCE which is an estate and has its own particular history, I'd suggest skipping the others and concentrate on the last two. If you have the time, you can spend the night in Arezzo before heading back to Florence (assuming you fly out of there too).

I've tried to work in most of the places you've got on your list, to tell you which ones are possible and doable without rushing between each place just to check them off a list.
Tuscany isn't that big and places are close to each other - which is good when moving around but Tuscany is also very CONCENTRATED.... in historical buildings (castles, fortresses, towers, amazing churches and abbeys and much more) as well as museums and art.... and that's not even considering the landscape, often covered with vineyards and the various colors of wheat, sheep, cypress trees and so much more --- I don't suggest rushing!!

Definitely do NOT try to just check off things of the list - keep the list but remain flexible and adjust each day according to how you feel like taking it. When we are out an about, we hardly ever do more than two towns in a day because we want to see what each place has to offer, as well as enjoy a tasty meal which often means being SLOW :D

As you don't mention Florence at all, nor Pisa or Lucca, I imagine you've already visited before and have decided to concentrate this trip on central and southern Tuscany. So whatever you don't fit in, can be left to another future trip ;).


New member
Ciao Lourdes,
Your a real expert, the best :))) thank you so much for your detailed organisation.
You helped me a lot. I will take into consideration all your advises.
Thanks again.


The Tuscan Expert ;-)
Staff member
you're very welcome! and if you have any other questions, feel free to ask!