How to split 6 nights in Tuscany

We split our stay between Siena and Montepulciano
Pienza is also lovely, might stay there next time as it’s a bit flatter than Montepulciano ;)

I agree with Christine: two bases make sense to limit day trip drive times. Siena is hard for parking, though, so maybe stay in the countryside at an agriturismo. We like Montalcino very much as a base twice. Don’t miss the Abbey of Sant’Antimo (closes noon to 1500 last I knew) near Montalcino.

We never have had trouble finding parking in Siena.

There is a wonderful hotel right below the walls of SG [10 minute walk], the Relais Santa Chiara; comfortable, very good breakfast, parking on site. See booking.com

Val d'Orcia:

https://www.wanderingitaly.com/maps/valdorcia.html

If choosing Montepulciano, try for a room at the Locanda San Francesco. Right up the street from Piazza Grande, next to the exit road out of town.

For "agriturismi" it would be Marciano, right outside of Siena; La Fonte near Montalcino.

Read this about driving in Italy and restrictions involved [ZTLs]; never leave anything of value in a vehicle when parked:

http://driventoit.blogspot.com/

My wife and I visited Tuscany in Aug-Sep 2019, staying 6 nights, dividing the stay between (near) Montepulciano and in Siena. This worked well for us.

First: 3 nights at a small agriturismo near Montepulciano, with a car (driving from Orvieto). While there we visited Montepulciano, Pienza, Montfollonico, and several sites near Montalcino (including Abbey of Sant’Antimo mentioned in the response from Laurel).

Then: we drove to Siena (stopping in San Gimignano during the drive), turned in our car, and spent 3 nights in a Siena apartment (with a day trip by bus to Florence). We were glad to have chosen Siena rather than Florence for these 3 nights, as it felt more relaxed (including having no street peddlers).

In case you are interested, I posted a review of the agriturismo on the forum: https://community.ricksteves.com/travel-forum/italy-reviews/near-montepulciano-outstanding-lodging-agriturismo-i-roseti

Parking in Siena can be a challenge, especially if you hit a festival weekend, but we never had any problem finding a spot in the underground lot at the train station. At 2 Euros per day it’s probably the best bargain in the city. From there a series of escalators will take you up into the center of the town - pretty slick actually.

Elizabeth,

I suggest you map out the distances on Google maps, The driving times they list may be a little optimistic, but they are close enough.

Then, you can decide how much time you'll lose transferring from one accommodation to another compared the the additional driving time you'll incur.

While looking, see if you can find somewhere equidistant from Montepulciano and Volterra. We elected to use one location as our base and it worked well. We went as far south as Chiasure, just north of Montepulciano and as far north as Volterra.

Still, I can see the attraction of experiencing two agriturismos. I would stay in Montepulciano, then up near Volterra. That way you can go as far north as Lucca easily.

I very much appreciate all the great advice and ideas. We are thinking of day tripping via train to Lucca one of the days we spend in Florence. While more expensive (we won’t fully realize the weekly rental rate on the car), sitting on a train, reading, etc. seems a lot more pleasant than a 90+ minute car ride each way. What do you all think of staying outside the walls in Siena? I’ve found a couple of places that are a short bus ride or 20-30 minute walk to the middle of town. They’re also close to the road out of town for exploring places west and north of Siena.

We are thinking of day tripping via train to Lucca one of the days we spend in Florence. While more expensive (we won’t fully realize the weekly rental rate on the car), sitting on a train, reading, etc. seems a lot more pleasant than a 90+ minute car ride each way. What do you all think of staying outside the walls in Siena?

I'm a little confused by your response. I want to make sure I'm not confused. You are not going to have a car when in Florence, are you? You don't want to have a car then. Only rent a car for when you're in Tuscany.

While Siena and Florence are very different, they are both cities. My preference is to stay in the country or a smaller town for a different experience. You should certainly make Siena a long day trip (or even two), but there's so much more to explore in the region. I'd stay further away from Siena than you were thinking.

I also thought of another factor that may effect your decision. If you stay in one location in Tuscany, you may get a more favorable rate. Also, some desirable locations may have a week minimum stay that time of year.

Doug Mac, I'm so sorry for the confusion. We will spend 6 days in the Tuscan hill towns and then 6 days in Florence. We will be picking up a car in Chiusi, using it while in the hill towns and then turning it in when we arrive in Florence. We will be without a car the entire time in Florence. One of the questions my husband and I have been struggling with is how to get to and from Lucca. We considered a day trip from Siena (spending 7 days in the hill towns and 5 days in Florence) and a day trip from Florence (6 days in each area and taking the train from Florence) and decided on the latter because we'll be able to avoid the drive and take the train.

We (two adults in late 30s) were very happy with 3 nights in Volterra 4 in Montepulciano. Both made good places to drive to other towns and with enough to see/eat if we didn’t want to go far.

Robert's comment about parking at the train station is interesting - availability and cost

We plan to drive to Siena as a day-trip. Probably on Wednesday, which is market day.
I've read that the market is just north of the Stadio, along Viale Cesare Maccari.
I was considering finding parking near the Stadio and was concerned with the market making driving to those parking locaitons a pain

Does anyone have knowledge about driving/parking on market day?

If driving down on a market day you're best advised to get there as early as you can to find parking.
You can save yourself the hassle by just taking the train or bus of you're coming from Florence ... or any station along the line for that matter.
The escalators across from the train station make getting up the hill and into the town pretty straightforward - use Google maps to get your bearings from there.