5/6 day driving around Val D'Orcia region for first timers


New member

This is our first trip to Italy. Planning to be there around 20th or 25th of April and visit Rome, Tuscany, Cinque Terre and Venice. From my brief reading it seems that Val D'Orcia would be a great place to drive around to do a farm stay and see rolling hills, wineries, see cheese making etc. I thought of making Montepulciano as the base (we'll be arriving from Rome by train). Found a decent farmhouse close to Montepulciano.

My questions

1. Would Montepulciano be a good base as there are many car rental agencies around? Places of interest (again from brief reading) are Pienza, Montalcino, San Quirico, San Gimignano, Siena etc. Or may be rent from Montepulciano and stay somewhere so that all of these are not more than 30-45 away?
2. Would 6 days be too much? Should we split 3 days Chianti and 3 days Val D'Orcia? We'd prefer not to cram in too much unnecessarily.
3. Could you suggest a driving itinerary for this area?
4. I assume all the small towns have parking outside them (just like the villages in Provence) so we won't accidentally enter any ZTL areas?
5. Is Florence a must do? If so may be a half day trip by train would be preferable.
6. Looks like this is Easter week. Would anything be closed or overly crowded? I read the Rome can be very crowded so we'll do Rome on our way out.

Thanks in advance,


The Tuscan Expert ;-)
Staff member
Ciao beena, sorry I had missed your first post, didn't mean to ignore you!

I'll go down your list to make sure I get most everything:

1. the Val d'Orcia would make a great base, as will Montepulciano. Since it is on the eastern part of the area, and close to the A1, it will make it easy to get further away from the area on the days you want to do day trips. I would definitely rent a car once you arrive in the area and then keep it while you're in Tuscany.

2. 6 days is NOT too much! I would suggest a day in Montepulciano with wine tastings, heading towards Pienza and exploring the area in between. Another day between San Quirico and Montalcino, with a visit to Bagno Vignoni and the Abbey of Sant' Antimo.
Another day you head north towards Siena and visit for the entire day. You might want to include Monteriggioni too since it isn't too far outside of Siena, it is a charming small walled town! Take the SS2 for scenic drive.
Another day you can drive to SG and then into Chianti, driving around the hilltop towns.
You could spend another day in the area and do a day at the hot springs in San Filippo and explore that area of southern Tuscany.
A would recommend a whole day in Florence, if you've never been it is a must! You can take train in to make it easier, or drive up the A1, park at Villa Costanza which is a parking lot along the A1 and from there take the tram T1 into Florence's center. Once in the center, all the sights are walking distance.

3. Driving itineraries - once you're in the area, the roads you need to take to places are about the only ones you can take, and they are quite scenic ;)

4. Yes, all small towns have parking lots - as you arrive, follow the blue signs with large P to find them. Any ZTL areas are generally small in smaller towns, and just ensure that you don't drive into the main square in town ;-).

5. looks like I answered that above

6. Yes, it is Easter week but basically the busy day will be Easter Sunday when many things are closed (not restaurants) and Easter Monday. This article gives an idea of what activities you will find: https://www.discovertuscany.com/tuscany-events/easter-in-tuscany.html
Some will be busy, like Florence, with the Scoppio del Carro, so you can either decide you want to see it and brave the crowds or come any other day after. We will update the info we have on Easter if we see anything new come up! In any case, museums in Florence will be open on Easter Sunday and Monday in general but do expect them to be crowded.

Let me know what else I can help with, especially if I missed anything :)