As part of our vacation to Italy in October, we'd like to stay in Tuscany for four nights. I'm leaning towards the Val d'Ocia region but having a hard time deciding on the particulars, mainly whether to stay in town or out in the countryside. Any thoughts from those who have done both? My ideal would be to stay in an agriturismo, but I also like the idea of being able to walk somewhere for dinner, etc. There don't seem to be many agriturismos within walking distance of a town, but I have found a couple that look close.

Second, any thoughts on Pienza vs. Montalcino vs. Montepulciano as a base? They all look great. Or any smaller towns in the region we should consider?

Thanks!

I stayed in Pienza and enjoyed the town although it's small. I like staying in a town because I like wine with dinner and won't drive over dark, winding roads after drinking a couple of glasses. I also would not walk over these roads after dark, perhaps not even in daylight.

If you get anything smaller than Pienza it may not have restaurants or shops or anything else. The town part of Pienza is seriously small.

You should search on this board for Val d'Orcia as there have been lots of recommendations and threads on this subject.

Of the three, I would prefer Montalcino as a base. It's a nice town, very attractive, and small enough to walk easily from one end to the other. It's a little bigger than Pienza, and there are plenty of restaurants and places to stay. I would definitely stay in the town rather than outside, because it's on a hill, and a rather steep one.

Montepulciano is also nice, but for some reason I preferred Montalcino. Montepulciano is strung out along a ridge, and there was a fair amount of climbing and descending inside the town.

Pienza is a good deal smaller than either of these. It has the advantage that it's an easy drive from there to a main road, because it's not as high up as Montalcino and Montepulciano.

I actually prefer San Quirico as a base location---halfway between Pienza and MOntalcino. Very authentic !

I took Bob's advice when we went to this region and stayed in San Quirco. Easy place to drive from, and more importantly, park the car, since it is flat. And, FWIW we have discovered in our travels they we are definitely "in town" people -- that is why we enjoy traveling to Europe: to be a part of another style of daily living and enjoy a pedestrian way of life.

Junebug,
Try http://www.lacrociona.com/ it is walking distance, 20 minutes, into Montalcino. It also has a restaurant in the village about a 100 meters from the apartments.

If going the end of October this may interest you http://www.prolocomontalcino.com/en/...-of-the-thrush

We stayed at lovely property outside Pienza (La Saracina) and one outside Montepulciano (Villa Poggiano), and loved both locations very much. We also had no issue with driving to dinner as opposed to staying within the villages. We will be staying outside of Montepulciano once again this May. We enjoy staying in the countryside. As between Pienza, Montalcino, and Montepulciano, IMHO, flip a coin. It is like choosing between fabulous and fabulous. San Quirico is equally fabulous.

Thanks all! I will check out San Quirico, hadn't considered that town yet.

Henry, I had actually just come across La Crociona- it looks like that could be a good solution for us. I also saw this one outside Pienza- smaller but looks nice- has anyone stayed there?
http://www.poderesangregorio.it/ilcasale.en.php

It gets dark early, in October. We have driven at night in that region. I really disliked the drive: the hilly, twisty roads are a torment. Accordingly, we prefer to stay in town, so we can walk to a restaurant.

All the towns mentioned are attractive.

I happen to prefer Montepulciano for its distinguished architecture and the variety of good, reasonably priced places to eat.

(Everyone has his favourite town and none of us can be persuaded that the others are as good.)

Driving into Montepulciano is a challenge the first time but after that, we had no problems.

Junebug,

I stayed in Montalcino 3 nts and loved this little town. Did day trips to Montepulciano, Pienza, Monte Olivetto and Sant'Antimo from there. I really enjoyed wine tasting in the Fortezza enoteca at the top of the town, dinners at Grappolo Blu and the views! Did not have time to visit San Quirico.

My visit was back in 2005, so my hotel rec would probably not apply.

Driving in/out was easy and the hotel did the parking/retrieving.

Driving in the countryside is a breeze. Enjoy!

We are also "in town" folks. We did it in Spello and Orvieto. I love being up early and going for a walk and getting the feel of the place.

We have an apartment booked in Montepulciano in June.

I almost booked this one in San Quirico and plan to check it out while there.

http://www.vrbo.com/204437

Bookmarking

bookmarking too!

me too.

Several years ago Bobthenavigator did a post on his favourites in Tuscany. As a result of this we stayed at Locanda di San Francesco in Montepulciano. One of the nicest places we have ever stayed. Montepulciano is great, especially after the tour buses leave in afternoon. Locanda is not exactly cheap, but it is great. And then there is the ajoining wine bar. Had wine with all the guest every afternoon.