My fiance and I are planning our honeymoon in Tuscany. We would like to stay in two different towns and were debating between small quaint towns (i.e. Montalcino, Barga, Cortona) or more medium size towns/cites like Siena or Lucca. We are worried that the small towns may not have enough to keep us occupied or not enough places to eat, etc. While at the same time we dont want to miss out on that small town ambience. Any suggestions?

I spent 1 week in Cortona last spring and loved it. It is a central location for many day trips, whether you take a train or rent a car. There is a museum in the town, and several restaurants so you won't have a problem eating. It all depends on how small a town you want.
The Hotel I stayed at was the San Luca, a short walk from the center of town, with a great view of the valley.

Then why not stay in one small town and one medium size? I would recommend Pienza over Montalcino for the small town. There are a good number of restaurants in Pienza or Montalcino. You didn't say how many nights you have. Three nights in a small town and three or four in a larger town would be great. Lucca and Siena are both good choices. Siena is close enough to Montalcino or Pienza for any easy day trip - 45 minute drive.

You are on your honeymoon in Tuscany, how much side action do you really need?! We stayed 4 nights of our honeymoon in a lone agriturisimo just N of Montalcino and can't wait to go back some day. Montepulciano was one of our favorites, Pienza and Montalcino not far behind. We also loved San Gimignano. Found Siena a bit busy.

BoulderCO: I'm curious...why would you recommend Pienza over Montalcino?

I just find Pienza more charming than Montalcino - I can't really say why. It does seem like Montalcino is top-heavy in wine stores and does not have as much variety in shopping as does Pienza. Also in my opinion the overall architecture of the buildings and layout of the town is more attractive.

I agree - Pienza is the best!

I disagree--Pienza is flat and bland compared to the " Mont" towns. And, whereas Pienza does have a couple of good ristorantes, there are at least 5 in Montalcino. If you have trouble walking then spend time in Pienza. If you want to see real hill towns go to Montalcino, Montepulciano, and Montefollinico--or even Monticchellio, which has an excellent ristorante.

I say PoTAYto and you say PoTAHto... lets call the whole thing off... smile

Yes, Pienza does not have Mont in it's name but it is most definitely a hill town. It is relatively flat walking versus Montalcino or Montepulciano. I love Montepulciano by the way but for some reason I never cared for Montalcino.
Taverna di Moranda in Montechiello is an exceptional little restaurant. Definitely worthwhile if you are staying in the area.

We had a fabulous meal at Taverna di Moranda several years ago. Stumbled upon it by accident. Montecchiello is halfway between Montepulciano and Pienza on a back road with spectacular views.

Please don't tell me that Montalcino is one of the steeper hilltowns....

One of the reasons Pienza is such as attractive town is that Pope Pius II decided in 1459 to transform the look of his birthplace. Under architect Bernardo Rossellino Pienza became the first town to put Renaissance town-planning concepts into place. The buildings in Pienza are great examples of this new vision of urban space. The square known as Piazza Pio II, Piccolomini Palace, the Borgio Palace, and cathedral are highlights.

Pienza is definitely on my short list of hilltowns to get to on my next trip in March.

Hi after this long discussion I would suggest you to chose a place far from the tourist masses, that is to say the small villages of Chianti, where I own a house too, and then decide daily what your plan will be a week will fly, but at least you can apreciate waking up with sun and birds singing as I do in the village of Lucolena, near Greve in Chianti. We also rent flats, just you might be interested, write me [email protected]

Fear not the small Tuscan towns. They can be quite scenic, memorable and friendly. However, beware the town so small you've never heard of it.

We stayed in Cortona (great place), but had to find lodging elsewhere on the second day (our hotel was booked for All Saints Day). The inn-keeper set us up with his buddy in the nearby "town" of Portole...which turned out to be 3 buildings, 2 people, and 1 dog.

We kept driving.