We will be traveling to Italy and basing in San Gimignano for 4 nights at Antico Pozzo for the 1st leg of the trip.<BR><BR>We then move south to our 2nd base to tour Montalcino, Montepulciano, Pienza, and the abbeys in that area.<BR><BR>Our plans (right now) are to stay in Pienza at Il Chiostro. I liked what I read about Montalcino and Montepulciano, but could not find lodging that seemed right. We don't need (or want) fancy, but like "rustic upscale" sort of places. We like smallish (under 50 rooms), with charm and character, and not a "hotel feel" but do not like B&Bs. For our first trip to Italy, we really don't want "self-catering" either.<BR><BR>My dream was to stay in some sort of farmhouse style place to really experience the beauty of the country, but my husband wants to stay "in town" so that we can walk to restaurants at night.<BR><BR>Is there some compromise either in Pienza, Montalcino, or Montepulciano? Somewhere on the outskirts of town but that would allow us access to the town without much driving? I know I'm asking for the best of both worlds, and probably being unrealistic, but doesn't hurt to ask. <BR><BR>Any suggestions would be appreciated, keeping in mind what we are looking for. We are willing to spend up to $250/night.

I don't have hotel suggestions, but Pienza is a great place to use as a base. I agree that it is much nicer to be able to walk into town. We stayed in an isolated farmhouse in Tuscany and it took a long time just to get to the main road and then a long drive just to get to the nearest restaurant.

This post sounds like it needs the Michael Paine of travel agents. Hmmm... Maybe a new idea for the Travel Chanel.

Hi Debbie!<BR><BR>We stayed at a small hotel (I think it was about 12 rooms) in a tiny Chianti village. The village was just big enough for an evening stroll and had a small trattoria (excellent) as an option to the hotel dinner. No shops, only tourists were at the hotel. <BR><BR>You might try for a place like this, but nearer to a larger town.<BR><BR>Good luck!

We're staying at Il Falconiere outside of Cortona. A little further than Pienza, but we're planning on day trips to Montalcino, etc. It looks to be about 45 minutes driving or so.<BR><BR>Our friends stayed there and enjoyed both the villa/hotel itself and being near the town of Cortona.

I really loved Vecchia Oliviera in Montalcino and I think it meets your description perfectly. It's not a hotel, and not a B&B, not fancy, but perfectly lovely and comfortable. It is located right at the gate to the town, overlooking the beautiful countryside, but within easy walking distance to everything in town including all the restaurants (the town is small and wonderful). It is a former olive oil mill converted to an inn, with a dozen rooms or so. There is a small pool in the backyard. Free parking is in the back. They serve a very good breakfast in the morning. The owners speak English and are very helpful. Rooms have air conditioning. Our room had hand-painted murals on the walls and a beautiful spacious bathroom (it lacked only a shower curtain, like most of the places I've stayed in Europe). Several of the rooms have jacuzzi baths. We were there for 3 nights last August and our double was $150 US per night, but it is higher at certain times and may have gone up since then. They have a website at http://www.vecchiaoliviera.com/ (you can e-mail them directly to ask about rates and reserve) and you can see more pictures at http://www.tuscany.net/oliviera/

Debbie - definitely stay at La Chiusa in Montefollonico. It is rustic yet very upscale. They think of everything! They have enormous jacuzzis in huge bathrooms. There is a beautiful garden and a restaurant attached. The views from the rooms and patio overlook San Biagio and the Montepulciano valley. The web site photos that I found before going did not do nearly enough justice to this place. I was actually a bit apprehensive before we got there. However it turned out to be the most relaxing, beautiful stop on our whole trip. I would say it is idyllic. From the hotel it is a 15-20 minute drive to Pienza, Montepulciano, or Torrita di Siena. All of those are lovely spots with restaurants, etc. I would go there again in a heartbeat. The staff is so courteous and the food is fantastic too! Good luck.