I swore I could figure this out on my own with enough reading here and elsewhere but indecisiveness and doubt buzz through my brain. I've even gone so far as to ask this question the wrong way the first time.

Here it is: Southern Tuscany - Val d'Orcia, ValDiChiana areas preferably. The age old question of which town. Yes, read lots of the same sort of question asked in various ways over the years.

Parameters: Planning on a self-catering (kitchen) apartment <b>in</b> a nice hilltown for 7 days before moving on to another apt in Venice for another 7. Not looking for an agriturismo or hotel. This is more about the quality of the town itself. Have found several nice looking rentals, some even with views from the edge of town in Montepulciano, Montisi, Pienza, Montalcino...

The tough part (and highly subjective, I realize, but that's ok): Wouldn't it be great to find this town has &quot;warmth&quot;. Not sure how else to describe it. Wine, views, wonderful old buildings and streets. (Is there a Tuscan hilltown that doesn't meet this description??). But how about a population that's visible, an outdoor cafe, a non-frentic public space somewhere. Large enough for a couple of choices for dinner and a walk afterwards thought the streets. This is all probably over-romanticized I'm sure, but I'd read someone account (can't remember where) of watching the older men in town playing bocce ball every night. That seems like what we're looking for, if it exists. Life, without so much running around, site to site. We'll play sightseeing in nearby towns by ear.

So, does this place exist?

I would pick Montacino, I think it has all you are looking for. Remember though that alot of the houses to rent are not within walking distance of the towns. I would prefer one within the town walls if I were you, what a good idea you have.
I have rented homes five times in Italy and France and so far they are all farther from town than I realized when booking them.

Thanks Natalia. I've been trying to watch out for that too. Making sure I see pictures, and see things like &quot;historic center&quot;. Montalcino did seem nice, at least from photos.

These were a couple I was just sitting here considering.

http://www.montalcino-tuscany.com/matteotti.htm
http://www.tuscanhouse.com/benincasa/apt.htm
http://www.terrazzadeifilosofi.it/

I've learned to watch out for those doctored pictures from other trips. Although it's not about where you sleep, if you're staying for a week, I figure it should feel a little like home.

My dog, my fish, and I all vote for Montepulciano.

MP has one of the best views around, especially the view from the dining rooms of Cafe Poliziano (best espresso in MP, IMHO). Getting wine is not going to be a problem. MP's main piazza is reminsicent of Piazza della Signoria in Florence -- mostly because MP's town hall is a white replica of Florence's Palazzo Vecchio -- and you can just sit in the tables of Bar Duomo all day long and do nothing.

Furthermore, any town where a shopkeeper can remember an anonymous American tourist (me!) coming back to his store after three years gets high marks in my book.

MP is also a good logistical base to see southern Tuscany (Montalcino, Chiusi, Cortona, Siena) and Rome, Florence, and Umbria as well.

Go to www.slowtrav.com/italy and start your search there.

Pienza and Montepulciano are both great. Personally I prefer Pienza because it is smaller and seems slightly more centrally located. I think it fits your description pretty well. I might prefer Montepulciano, however, for a seven day stay. There are only a handful of good restaurants in Pienza and shopping opportunities not as extensive as Montelpuciano. Both are very attractive hill towns. I have been to Montalcino a number of times to buy wine and it is nice but to me just not as attractive as the other two. I also find it to be a bit out of the way.

You can't go wrong with Montalcino, Montepulciano or Pienza. I agee with BoulderCo though on Pienza. We went to all 3 in June and Pienza was the hands-down favorite. It is very walkable (flatter than the others), beautiful town square and views, less crowded, etc. It seemed more manageable to me than the other 2, although I wouldn't miss the others. I will stay in Pienza next time I'm in Tuscany.

I've been going around in circles on this one , also. I decided on Montalcino. Why? SlowTrav. recommendations and a very quick and friendly response from Luigi and Isaballa Dusi at montalcino-tuscant.it.

Don't think you can wrong with any of them, though.

I went through the same process earlier this year and stayed in Montalcino two days in September. It was enjoyable, but probaly the least favorite place of a two week trip. It had more wine bars than restaurants. Many of the better restaurants are located outside of town in the vineyards. We were planning to go to Pienza on the way to Rome but missed the turn off. Met a couple in Rome who had just been and they loved Pienza.

Isabella Duisi and her husband are atually Austrailians who moved to Tuscany and did the usual thing by writing a book. It was a good one and I'll try to remember the title. I'm sure someone else here has read it too.

Thank you all for the time and thought you all put into your responses. So, Montepulciano, Pienza or Montalcino huh? I guess I saw that coming, but it is good to know that many people would dispel some of the thing I'd read right on this forum about each one. &quot;barren, Disneyesque, stuffy&quot;' respectively, is what I'd read. Thank you for offering up a counterpoint and I'm going on the idea now that any of these would be suitable.

I'm leaning towards either Montepulciano or Montalcino, I think, mostly for their position at one end of that 'line' or another. It probably will come down to the qualities of the rental then.

Logistically, Montepulciano is closer to Cortona, Perugua, Arezzo, which I like. But then, Montalcino is closer to Pitigliano and Volterra. Since we'll do most daytrips on whim (other than Florence), either presents great options.

Oh, and Dayle, I saw references to that book. &quot;Vanilla Beans and Brodo&quot;. Had thought about picking up a copy myself after reading an excerpt.

Having just returned from 2 weeks in Italy, with one being spent in Montepulciano, I may be a bit biased in my opinions. By luck we found on the internet the NICEST and very reasonably priced apartment (one of 4 and newly renovated with all amenities) which was within the walls of the city. That was a big criteria for us as well; to walk out the door and be in town. There is a laundry room, walled garden, free carpark (!) and a view you will never forget. I have digital photos and maps to share if you wish. The owners are two lovely sisters whose family has kept ownership of the property through several generations. They were warm, welcoming and helpful. With great pride, they gave us a tour of the ancient little town on our first day. If you see Under the Tuscan Sun, the flag throwing event is in the main square in Montepulciano. (We were also in Positano on the Amalfi Coast which was in the movie as well). There are many little shops, restaurants, wine caves, churches, and local artisans. Each day we drove to another area for an adventure, then back to Montepulciano for dinner, vino rosa and shopping. We have been to Europe several times but this was probably the most enjoyable. The only slight downside is that there is no train station in Montepulciano so you must go to another town for day trips. It was an easy train ride to Florence. Please let me know if I can provide any other info. The website to the apartments is: [email protected]
Enjoy! Ciao!

Coco, what a nice little paragraph. Did you do a trip report? Having just returned from a &quot;busy&quot; trip, this type of &quot;laid back&quot; vacation interests me. Would like to hear more.

Coco, the website for the apartment doesn't work for me. Have a better address?

Clifton,
Have you made a decision? I'm curious to learn what you find out because we're looking for the same kind of place. Good luck and have a great trip! Please report back to us.

Rhonda,
So sorry!

The [email protected] is an email NOT a web address--too much Under the Texan Sun for me since I have been home!

The first half of our trip was considerably busier since I insisted on returning to Venice while my husband was on business in Milan. That was a quick turn around but hey, to wake up in a room overlooking the Grand Canal--it was worth it. Then there was fabulous Positano and the Capri adventure! So many stories, so much fun and 'way too many photos!

Please let me know if you have any further problems with contacting the owners of the apartment!

Ciao!

Coco, wow, it took a little bit but I actually found a website with information and photos. Very nice. I think the scales have been leaning towards Montepulciano anyway, as Perugia and it's Etruscan walls are a day trip I thought would be interesting.

This sounds (and looks) like a great option. We're planning for sometime after July, likely Sept, as we go to Australia first in Dec. But I'm trying to be ahead of the game for Italy (obsessive?). This gives us some time to make decisions and reserve a nice place. Thank you for the personal recommend. It's good to hear from someone who's had the experience first. We'll talk it out over time, but this is very much the kind of place we'd talked about.

Modeen, no decisions yet, but I think Montepulciano is leading due to position; it's mix of options + small size and nice rental properties. The more we talked about this, the better we liked the idea.

Here's the URL I googled. Coco, is this the place?
http://web.tiscali.it/no-redirect-ti...o_ing_home.htm

Clifton: Yep, that's it! I hope I have not over hyped Montepulciano. Here's what I found about the locals--didn't really see them much! I think they may be indifferent to tourists because they see so many. Before you decide to stay there, ask Margherita and Elena if they can suggest places where the locals hang out. They spoke to us about restaurants in town but perhaps there are others just outside the city walls catering to locals. We mostly saw tourists everywhere we went (&amp; unfortunately a few ugly Americans from whom we distanced ourselves!) who were very friendly and full of stories. Many years ago, we stayed with an Italian friend and his family who lived on the Adriatic coast. It was a fabulous experience but being friends with their son in America made a difference.

As you can see, I'm full of chat. I just want to be careful not to dissuade you from what your instincts tell you. Bottom line is that we never saw anyone (as in Under the Tuscan Sun) who was dancing in the fountain or playing bocce ball. Other good news is that we felt 100% safe?no druggies?no gypsies. For me,the scariest things were the traffic (however, I love Ape trucks and Fiat clown cars) and mystery meat.

Coco, well, I guess if we end up choosing a well known town, whether it's Montepulciano or somewhere else listed in every guide book, there's sure to be some effect that tourism has had on the place. Originally, we were talking about other towns and discussed staying in Sinalunga. Went so far as to Pose a question about Sinalunga, but the general consensus was that it wasn't a particularly charming town. Also considered Asciano and Trequanda, but like most non-touristed towns, the options for lodging, dining, etc were narrowed considerably. I guess when you get down to it, the famous places are famous for a reason and those perfect undiscovered gems are something long gone or awaiting the arrival of a Rick Steves type!

We'll likely stick with Montepulciano or thereabouts and keep a map handy for slipping off to other towns. It's our first trip to Italy, so really, a tourist oriented town probably isn't a bad choice for a first run. Maybe we'll slip off to a Montefollonico, Torrita or Cetona for an evening or two just to see what's happening on Main St, or the main piazza, as it were. Maybe we'll make our own discovery for next time.

You've been a great help and we appreciate the replies!

Montepulciano is a nice place to base yourselves, for one thing it is not too far from the roads that will get you around the area. Sometimes that can be the problem when you have to drive for miles just to get to a main road (when you do it every time you go someplace).

We usually take the main road to the farthest point that we want to travel that day, and then slowly make our way back on the small scenic roads, this way we are closer to home later in the day and can decide to return later after we have scoped out a place, and you don't have to rush though a town to get to your destination.

I am writing this from experience: my first rental was so far from a main road (in the hills near Volterra) that it took ages to get to main intersections, we would come back after midnight many nights in the fog.