We'll be five days in South Tuscany (Montepulciano) next Easter. It's our third time to Tuscany and we have some knowledge on the area but we'd like to know if "the fodorites" can give me any advice about hidden or unknown places to go.
Our plan trip is:

Day 1: Fly to Rome and drive to Montepulciano (stop in Orvieto).
Day 2: Arezzo and Cortona
Day 3: Val d'Orcia (Stu' itinerary) (Pienza, Montalcino, Sant'Atimo, Montichiello,...
Day 4: Another day in Val d'Orcia or day trip to Siena-San Gimignano.
Day 5: Drive to Rome and return flying.

We travel with our child (2 years old), so we can't go very far.
Thanks,

Àlex

I would definately include Pitigliano in your itenuary - a real gem. The view approaching this little city is breathtaking. Another on of my "secret" places is the thermal waterfalls of Saturnia. Hard to find, but on a nice day - is a wonderful experience.

Thanks zkefman, I will consider Pitigliano.
Do all of you have more suggestions?
Is it worth to go to Trequanda, Montefollonico or Castigilone d'Orcia?
Has anybody visited the gardens of La Foce?

I would be sure to allow some time to wander around in Montepulciano. It's a small town but has a lot of atmosphere.

There is nothing much to do in Montefollonico, but it's a short distance away and very scenic. Trequanda did not have much to see, as I recall.

Enjoy.

Thanks jd dallas, I will not spend time in Montefollonico and Trequanda.

alex,

Trequanda is indeed small and with limited time, maybe not worth a tourist stop, BUT one of our favorite restaurants is there, Conte Matto...the food is really, really good and we had one of our favorite wines of the trip with dinner last visit...if you find yourself close by and are looking for a lunch or dinner place, this is a good one and would make a charming drive and short walk through ..also suggested on Slow Travel..

In our week in Montepulciano, we (inveterate drivers and roamers) never went more than 50 miles out from home base. But with all the twisty roads and the inexplicably slow drivers we felt we spent entire days in the car. With a 2 year old it would be tougher still. I think your itinerary is just right, though I suspect you may not make it as far as San Gimignano -- no great loss IMO.

Just getting to Siena (with stops and tiny detours) and back was a full and delightful day.

OTOH hand if you are so close to Siena, it would be a pity not to push on to see Monteriggioni.....(Note to self: NO, THAT WAY MADNESS LIES
...King Lear)

Traviata, thanks for your recommendation. We will consider Conte Matto for diner or lunch. What kind of restaurant is it?
Tedgale, I think you're right. We'll not go very far away from Montepulciano, but would like to know well all the country and villages around the town.
We have been in Monteriggioni and, you're right, it's impressive with its walls but maybe the village inside is just OK.

Àlex

Is Pitigliano the town that had a fairly large Jewish community at one time?

alex,

Conte Matto is a typical, informal restaurant with many local specialties where you would be very comfortable bringing a small child....the staff was really pleasant and the waiter took time with us to choose our wine, one that quickly became a favorite .....Trequanda is not a big tourist town so you know they are feeding mainly the locals...food has to be good!!