What are the best Hill towns of Tuscany

Having a car gives you the ability to see lots. Folks here will urge you to take a GPS loaded with Italy maps. Buy the regional Michelin map there if you don't.

From Montepulciano, you're in easy reach of Siena, and its beautiful public square and cathedral. San Gimignano is not too far away. Montalcino is also in that direction.

Well, like you said, there is so much to see, so it's tough narrowing it down to just a handful of places. Also, in terms of interests, is it primarily churches and monasteries, art, small town atmosphere, wine, all of the above, etc.? But, here are a few possibilities, each group of towns are right nearby each other:

(Right near Montepulciano..) Pienza, Montalcino (wine), and the Abbey of Sant' Antimo ;;; Cortona (along with the monastery at Le Celle), Arezzo, and Lucignano (small town) ;;; San Gimignano, Volterra, and Monteriggioni (small town);;; Siena, of course ;;; (In Umbria...) Orvieto, Civita di Bagnoregio (small town), and Todi ;;; Assisi, Torgiano (wine), and (possibly a little further afield..) Gubbio.

You certainly don't need to rush yourself and visit all these places. The key is to pace yourself. This is just to give you a few ideas of which towns worth visiting are in which areas. So if you're going to visit, say, Assisi, you could also stop by Torgiano to get a small sample of wine to take back with you to your agriturismo.

Anyway, sounds like fun! Hope this helps! Enjoy your trip!

The road from Montepulciano to Pienza and Montalcino is very nice as are both towns.

Unless you've already been there, don't leave out Florence just to see the hill towns. Michelangelo's David at the Accademia will stop you in your tracks and his painting of the Holy Family at the Uffizi is truly magnificent, and you simply MUST climb the 400+ steps to the top of the Duomo. What a view of Florence and Tuscany. Nothing better. On the way down you can almost reach out and touch the paintings on the ceiling of the dome. Then there's the Baptistry in front of it that you won't want to miss, and the Ponte Vecchio, and .......

It's probably just me, but after three hill towns and their respective cathedrals, town squares and shops they all started to look the same. Not true though of Siena, where you can spend a day or two. If you do go to Florence, look for a train stop with parking some distance from the city. From the train station you can walk everywhere. You really don't want to drive in Italy's big cities. They're nuts. Have a great trip.

We had a few days between CT and Florence then between Florence and Rome. We were traveling late October. Weather was great and crowds weren't bad. Here's our opinion of the places we stopped.

We visited:

Pisa, glad we went, probably now that we've seen it once won't go back.

Lucca, nothing special, won't go back, could have gone somewhere else. (People like it perhaps because it's quieter than other crowded towns in summer and it's flatter than other towns).

San Gimignano, loved it, the medieval city really stokes the imagination. It's a tourist town but prices weren't higher than other places we visited. Probably would go back although I like to see new places.

Siena, loved it, will go back for another look.

Orvietto (Umbria), loved it, more sites than we expected.

I'll edit this as more places come to mind where we stopped.

I have to say Montepulciano is one of my very, very favorite towns. Small enough to be charming, big enough to have variety and unexpected gems. I marvel at how they turned some of the old gates into apartments (Farina gate for example) but, perhaps I'm easily entertained by the small things.. Anyway, I think you will like where you are staying.

MP is a bit touristy--it's always been a haven where wealthy Romans escape the summer heat--but it's not tacky-touristy. This also means there is a surprising amount of life during chiuso and on Sundays-- by Italian standards.
Most of the tourists we met and talked to were not from the US, so that was nice too. It's charming and uncrowded during the shoulder season.

Some advice, 1) it will be cooler than Rome and the lower elevations, bring an extra layer. 2) Don't miss the coppersmith's shop (Bottega del Rami) on Via dell'opio nel corso 64. All the cookware is handmade by the owner at his shop on the next street. It's functional art-- let them ship it home and you don't pay the VAT.

I love the other hilltowns (mentioned above), find them all delightful--not repetitive-- but I don't go on and on and on about them as Montepulciano. My next favorite towns are ones we found for ourselves on the map that are not in any tour book, do not have "e-ticket" attractions, are actually populated by people who do not converse in English, and feel like our private discoveries. Try this at least once.

One last piece of advice, RS Italy & RS Tuscany/Florence books are very weak on the Southern Tuscany hilltown experience and he completely ignores the Chianti. RS books concentrate on destinations along train/bus lines. So, even though he has some good shows on these towns, you should DEFINITELY buy another guidebook that covers this region.

This Italian website is a site promoting smaller, beautiful towns and villages in Italy. Click on the placenames for more information on each place.

http://www.borghitalia.it/html/borghi_centro_en.php

Here's an article on this from Rick's Best Destinations http://www.ricksteves.com/plan/destinations/italy/hilltowns.htm