I'm going in May and will be staying in Montepulciano for one week. We will also have a car.

These are the places I would like to see. I would like ideas on pairing smaller towns so I can see 2 in one day, if possible. I know there are lot of places so I would appreciate your input of which should be eliminated or if I should another place not listed.

Pienza
Montalcino
Orvieto
Volterra
San Gimignano
Siena
Chianti-Radda, Greve, Castellina
Spoleto
Assisi
Cortona
Arezzo
Olvieto Maggiore
Florence-Good idea to take the train?

Ok-so the list is quite long and I probably won't be able to see it all. I would rather spend all day in a town where I will enjoy it instead of rushing from one place to the next just to "see" it, even if that means I will have to go back some other time to visit the places that I did not get to see.

Also, can anyone give me estimated travel times for each town from Montepulciano or direct me to a website where I can find that information?

Thank you,
Mariana

PS-Thank you for your help so far. I don't post too much because I have gathered a lot of info just by doing a search on this board and it has been very useful!

Anyone?

Your list sounds like a good one to me. Some of these villages are so small that an hour or two will be plenty. Others will take longer. Just group them by location. Pienza and Montalcino are in close proximity. Volterra, San Gimingano and Siena (altho you may need two days for this itineray). Some of the larger towns may need a full day. I would suggest you go to www.michelin.com and put in Montepulciano and each town to get an idea of how far and how long it takes to drive each route. There are others on this forum that can give more advice on how to plan your trip. We saw about half this list in five days, and we didn't go to any larger places - Florence or Arezzo.

All Tuscan towns are, as far as I know, in Italy. (Sorry, I couldn't resist...) And some of the towns you mention are in Umbria.

Your list is far, far too long for a week. And anyone who can see Florence in a day trip has my highest admiration. (In my personal opinion, three days are the minimum to see Florence).

If you are still reading, here are a few suggestions:

From Montepulciano, you can visit Pienza and Montalcino in a day, probably including Monte Oliveto Maggiore (which I, personally, would give a miss, not being very interested in Il Sodoma or Signorelli). I would definitely add the Romanesque church of Sant'Antimo near Montalcino.

Siena is a day; if you push it, you can do San Gimignano the same day (arriving in the late afternoon after most of the day trippers have left).

Many people like Volterra; I do not and would omit it.

I don't know them, but I would think Radda, Greve and Castellina could be done in a day.

Each of the Umbrian towns deserves a day at least: Orvieto, Assisi and Spoleto.

I'm not sure how you would fit in Arezzo (which, as far as I am concerned, is only of interest for the Piero della Francesca frescoes in the church of San Francesco), and I have never been to Cortona.

Not knowing your interests (mine, I think, are fairly obviously for art and architecture), it is difficult to suggest what you should add or subtract.

I would suggest that you re-read whatever information you have on each of the towns and make your own decisions based on your own interests.

The towns we most enjoyed in Tuscany and Umbria were Siena, San Gimignano, Greve, Orvieto, Montepulciano, Spoleto, Assissi and Perugia. We stayed just outside Spoleto in a little B & B called La Macchia. Inexpensive and has a charismatic restaurant with very good food.

We didn't enjoy Volterra either.

Although it is very touristy Siena is a must but the traffic in early evening can be dreadful so get out of there early if you are not staying in the town.

I've stayed in Florence for three days and visited some Tuscan towns for another five (and certainly not all on your list), and - unfortunately - haven't visited Umbria yet. However, I'll throw in my very newby comments since they differ somewhat from others:

- thought Volterra was okay. If you're visiting San Gimignano (which I really enjoyed), I could happily suggest forgetting about Volterra;

- I'm ducking my head now - Siena, overall, was a disappointment, as was Pienza. I wouldn't return;

- Really liked Montalcino, Montelpulciano and Cortona;

- I agree with Eloise, the Abbey at Sant'Antimo is a "must-see".

Sent in the spirit of a differing opinion,

Linda

We stayed in Radda last August. It's quite small-- only about three streets long-- so there isn't that much to see. However, on the outskirts of Radda, we found an incredible lunch/dinner trattoria called LA BOTTEGA. Its set in the middle of the lush Tuscan countryside, and had wonderful food. Reservations are a good idea.

Greve and Castellini are also very small, but will give you a nice feel for the Tuscan countryside. You might want to stop in Greve at the market ( I don't remember if the market is on every day or not.)

We found Siena disappointing. I don't think we'd make a point of going back. But we did love touristy San Gimignano, and had an excellent dinner there overlooking the valley at sunset.

Hope you have a great trip!