Tiller: I was there in Oct/04. It was cold while I was there, which might have affected how I felt. I think the steep streets was a negative for me as well. We did have a car, which I really recommend for getting out and seeing the area. I just remembered the name of a little town we visited, which was my favorite of the whole trip - Montichiello, not far from Pienza. I don't think I would stay there as it is very small, but it was so picturesque and as an artist, I took many photos for future paintings. Also remembered the name of the apt. in Montelpuciano - Poggiolo Apartments. Very nice apt.with parking and with a small balcony/terrace. Very nice to sit there with a glass of wine and enjoy the gorgeous views. If I return to Tuscany, I think I will stay in Pienza.

Barb:

Thanks for the reply. I've researched the other towns you mentioned, Monticchelio and Pienza. Montepulciano
had the best choices for apartments to rent. Monticchelio looks beautiful, and so many say as you, a favorite, but could be lonely. I guess the trade off for you, having a great apt(Poggolio) didn't offset your preference for staying in Pienza or San Quirico, where lodging is limited (apts) but the towns livelier? Where did you shop for groceries, in Pienza? I know Montepulciano is steeper, I don't know how that might affect one's stay other than the most obvious, I am very curious, aren't there alot of locals that live inside the walls of Montepulciano, or is it basically commercial? I just thought one would have alot of interaction with local citizens, staying inside the walls...I know we are going to spend at least a week in the area, in one of the towns...I just have to decide which is more important I suppose, a comfortable apartment for a family of 4 or a livelier town with a smaller accomodation and 1 bathroom!
I am an artist too, handpainted tiles, and my daughters, who are very creative, will very much appreciate the beautiful landscapes and all the details.

ttt

As I said before, it's just my opinion based on the circumstances while there (weather and travel partner who had a very hard time with all steep streets and steps. Pienza is more level and it just seemed cheerier to me. There are small grocery stores within the city, but most of the larger markets are outside. Interestingly enough, even though we didn't stay in Pienza, we shopped at a grocery store on the outskirts of town. I think there were some really good restaurants in Pienza, including my fav Latte Luna. One great little place right on the Piazza, can't remember the name, but I had THE best grilled pecorino, OMG, my mouth waters just thinking about it.

There are locals of course who live right in Montelpuciano, and I'm sure you could have lots of interactions with shop owners, etc., I just didn't think they seemed as friendly as other towns. Except, the lovely owners of the Poggiolo Apts. Two sisters who were very friendly and helpful. The apt. we stayed in with the small terrace had two bedrooms and two bathrooms. One bedroom had two twin beds and a sort of loft with another small bed. The other bedroom had a large bed. One bathroom had a shower and the other just a toilet and sink. In the large bathroom you could sit on the throne and look out the window over the rooftops - very cool - also heated towel racks. There was a fireplace in the living room and on the terrace was a built in wood barbeque. So, for a family, it would be perfect. You might love Montepulciano and, if not, you can day trip to lots of wonderful places.

We spent a week of our honeymoon in Montepulciano, and it was truly heaven for us. We were there in early June. I found the town charming and endearing- To me, it defined everything I dreamed when I thought of Tuscany (it was our first trip).

However, I will say that after the craziness of our wedding, we were really looking for a place that would be relaxed and intimate, rather than busy and bustling (we got that in Florence and Paris). The town enabled us to enjoy "slow travel" in every sense of the word. We were never bored, just completely and totally relaxed.

We spent a week there, in an adorable apartment called Politian (www.politian.com). We chose not to rent a car, and only left the town once. On that day, we went on a hike to Pienza, stopping in Montichiello. We really enjoyed NOT venturing out every day to a different place. Though we had plans to explore the bus routes to other towns, we found that if we really slowed down and looked, there were lots of interesting things to do in Montepulciano.

For example, we went on a "wine tasting tour" and sampled at many of the larger places, really tasting and enjoying the differences in each place. We also bought a little guidebook at the tourist center which really served as a detailed walking tour- it described many of the major buildings in town and the history behind them. We also walked down to San Biagio and spent some time there.

Every day we would have breakfast at Caffe Poliziano (at the bar, for 3 euros each). We leisurely lunches and long dinners, and were more than enough places to try a different one each day (though we returned to Acquacheta more than once!) We also explored all the little shops, including "the oldest shop in Montepulciano," which sold beautiful leather goods (my husband bought a briefcase).

The advantage of having an apartment is that we also were able to prepare meals for ourselves. Many of the stores sold jarred sauces, and so for a few evenings we bought ingredients to make our own Tuscan meal.

I would not advise driving your car within the town walls, and there's really no need to do so. You can walk anywhere, and there is a small city bus that you can take if your legs are tired.

If you're planning to daytrip to other towns, I would not overestimate the value of relaxation at the end of the night. Montepulciano may not have hopping nightlife, but after a long drive you may find that kicking back and enjoying a bottle of wine is the perfect end to your day.

Enjoy, whatever you decide!

Tiller, There is a lot more to do in Pienza than many think (many seem to go there for 2 hours and move on). I spent 3 nights there in Sept and never left. If you want more details about what is there and restaurants, here is my trip report:
http://www.fodors.com/forums/threads...p;tid=34687434

Have fun deciding!

Tiller,
We stayed in Montepulciano for a week last June. We really enjoyed the town. It was very charming and the people were very friendly. We rented an apartment that had incredible views. We enjoyed exploring the quaintness of the town, but we also did some day trips to other towns. One day we took an early train to Rome for the day. We travelled with our kids and only wanted to do a quick visit to Rome. We loved Montepulciano. As for shops, there are leather shops, linen, pottery, cookware, and many others. We bought a number of small gifts. And of course plenty of wine. The views are incredible. It is a wonderful and quaint town.

Hope this helps, have a great trip.
Travelatte

Hi Tarheels-
Sounds like a wonderful honeymoon!

How long did it take to hike to Pienza from Montepulciano, and what was the terrain like? Do you think we could do it on bikes?

thanks!
Dina

Hello dina! From what I recall, it took us about 5-6 hours to get to Pienza, not including a stop in Montichiello. However, it was very very hot, so we probably walked a bit slower than usual. If you're going in the summer, I would definitely recommend starting out earlier than we did! Also, be aware that during much of the trip there is no shade, so you'll definitely want a hat and lots of water.

The trip is pretty much along one major road, but it is very hilly. If you're a strong biker you may be just fine. There were some people that passed us on bikes, so it does seem to be possible. Perhaps someone else can comment on this?

Thanks for the info, Tarheels!
It may be too hot and too hilly to walk or bike in late June.
Our family loves to take bike rides, though, so maybe we can do something around Montepulciano??
Has anyone done this?
tHanks,
Dina

Dina4, I rode from Montepulciano to Pienza last year on bike. I don't recall exactly, but at a rather leisurely pace with stops for photos and water (there is some gorgeous scenery) it was less than an hour or so. The last hill up to Pienza though is a killer! This was one of the more traveled roads I rode on that week, but I didn't think it was dangerously so.

Hi Amy,
Wow, that sounds fun!

Regarding the hills, do you think you have to be in exceptional shape, or just good shape?

Are there other bike trails in the area?

Thanks for your help!
Dina

Dina, the hills are not easy, but you can always walk up them too! I spent that week on a bike tour of Tuscany so I was a hardened veteran by that last day in Pienza! ;) I am not in biathalon shape but I do work out a lot and managed 20-30 miles a day on average at that point in the trip. But of all the rides that week, that was the easiest until the hill up to Pienza. A lot of it between Montelpulciano and Pienza is either downhill or flat.

Thanks, Amy!

I have a VERY IMPORTANT question:
When you say that you park OUSTIDE the walls, or TOWNS, what do you mean? Where? is there like a parking lot?
Sorry for my ignorance, this is going to be my first time in Tuscany and I'm confused where to park in the small towns.

We stayed in San Gimignano (La Cisterna Hotel) and parked outside the walls. It was a great homebase for touring the small wine towns. San G is packed during the day (when we were gone) and then when we got back in the evening it was peaceful and charming. Since it is a big daytripper destination there is an above average number of restaurants. Have lunch at Il Pozzo if you get a chance (in Montereggioni sp?)

ItalyLove, I can speak only for Montepulciano, Siena, San Gim and Pienza...but literally, there are walls around the town and it is either impossible or next to impossible to drive and park within them. At all of these towns I visited, you parked outside the walls (sometimes just outside them, up against them!) in lots or on the street and walked in.

We used an apt in Montepulciano as a base for a week and really enjoyed the town.

While there we witnessed a wedding celebration one day..and a funeral procession another day. The people marching throught the streets...and especially the reacion of the locals...reminded us of the Godfather.

If you go, be sure and see the copper (http://www.pbase.com/dickp/image/22954598) and woodworking (http://www.pbase.com/dickp/image/22954604) workshops at the top of the hill. It's like going back a 100 years.