Reconsidering base for Tuscan hill towns with car.. Montepulciano or Siena???

Hello Laura,
A bit more complicated as you need to go east, west and south.
Looking at google map with distances and time, i would probably base myself very close to san quirico d'orcia.
Seems centered in terms of time to get to the twns you want to go

I don't know what the Heart of Tuscany drive entails but that and the areas you mentioned entails 4 days at least, not including Montepulciano itself, and a lot of driving. Close by worth visiting are Pienza, San Quirico, Montalcino, Monte Oliveto Abbey, Lucignano, the less visited but charming Sarteano, Cetona, Paciano and Panicale. I liked both the old and newer sections of Chianciano. Orvieto is a good day trip if combined with Civita beforehand.

Laura, even if your hotel includes a ZTL pass of some kind, I would not want to say "in" Siena with a car. It would just be a drag.

While I endorse planning, we drove pretty long distances, and enjoyed the scenery. I think your planning time is more valuable finding market days, special attractions, secret places, the best wine or food, and so on. Just for completeness, we stayed in Sinalunga, at a luxury, smaller resort, that was in a satisfactory place for us. Not saying you should consider it, at all.

We recently stayed at Relais San Bruno located in Montepulciano and loved it. What's great about this place is it's outside the city itself so you get be in the countryside while still very close to old city. The owner, Alberto, is wonderful. He is a tremendous resource for what to do and where to go. I loved staying there and hope to go back. If possible, try to go to Podere I'll Casale for lunch and a tour. The setting is beautiful and the food is great. Reservations are needed. It's located outside of Pienza.

By the way Montepulciano is wonderful and not overrun with tourists as in some other cities, like Pienza, because there isn't any easy access for the tourist busses.

Have a great holiday!

We have stayed on both Siena and Montepulciano. Although we loved Siena, I feel Montepulciano would make a better home base for day trips. Better parking available and a wonderful town on its own. Easy day trips to Oienza and Montalcino, Cotona, Assisi and Orvieto. We prefer being right in the heart of the historical older part of the town. It is a town to explorer by itself, that you can do when you get back from dat trips.

We were doing this trip May 2-8 this month and stayed in Siena. Loved it but we too would stay in Montipulciano if we go back. We loved both places and Pienza too. But the distance to Orvieto and Assisi make Montepulciano a great pick to say nothing of the beautiful town. We drove hwy 146 and wow, we so loved the area and found it breathtaking. You have much to look forward too. We also went to Voltera. From Siena The drive was easy to Voltera and south to see the sword in the stone. But it came at a price. The distance to drive to Assisi or Orvieto we felt was just more than we wanted once getting there. So in my opinion and since we were just there, decide what you must see first then make it easy on yourselves to follow through. My visit was mainly about Siena but we also enjoyed Arrezo and Anghiari. They were easy to get to and return by car. Assisi we declined to do but would have more likely gone to had we stayed in Montipulciano. Same about Orvieto. Don't forget to stop alongside hwy 146 to see the small chapel sitting out in the hills. Our least favorite was Voltera in comparison to Pienza and Montipulciano. Those two places are just so pretty and relaxing to be in. Do a day trip to Siena. A full day.

Any place will do. Siena has easier access to freeways, and better located to visit Volterra, San Gimignano, Chianti area, Monteriggioni.
Orvieto, Assisi are equidistant from either.
Siena has more life in the evenings.
Be aware of traffic restrictions (ZTL) in the historic center of both. Make sure you choose accommodations accessible by car outside the ZTL.

We have stayed in both Siena and Montepulciano. both are wonderful place and although Siena has the stunning Campo for that evening drink, both have lots of restaurants and in our experience we had better luck with food in Montepulciano. To us the advantage of Montepulciano was that we could easily drive to other towns, abbeys etc. Siena is a big city and there is a lot of sprawl to get through to get to the countryside. The historic center is wonderful though and you won't go wrong either way.

Janet,
Have to agree about the amount of"sprawl"you need to drive past leaving or coming back to Siena. It goes quick but if that bothers someone they may want to stay outside of Siena. We stayed inside Siena but I did drive past the Hotel Athena, I can say I saw plenty of parking there and while I did not stay there that location is a good one for ease of coming and going from Siena. Worth looking into. Nice area too.

Just spent four nights at Borgo Casato, about 20 km outside Siena in the hillside. Relaxing!! Great breakfasts included in the very reasonable price, excellent restaurant dinners (also very reasonably priced) and easy access to good highways while still feeling like countryside.

Thanks all for the advice... I am leaning toward Montepulciano since it sounds like a better centralized location for the towns we want to visit. I will still want to spend at least one late afternoon and evening in Siena. Charlie, where did you stay? Maybe staying in the old town would be good as you say for exploring in the evenings after our day trips.

Laura, We stayed at the Hotel Duomo http://albergoduomomontepulciano.it/albergo/?lang=en and the Camere Bellavista https://www.camerebellavista.it/en/ and both were great. They are in the old historical area on top of the hill at the Piazza Grande. Both had parking available.

Thank you!

I've stayed twice in the Politian apartments in Montepulciano (politian.com) at the top of the hill and love, love the apartments and the folks who run them. Giacomo and Maria, brother and sister, are wonderful people, easy to deal with, speak English very well, and very helpful learning places to eat, things to do in Montepulciano. It's a bit tricky driving there the first time, but once you are confirmed they will email you a map of how to get there. Follow it exactly (not your GPS)! Once you arrive, they will give you a placard for your car which allows you to park right in front of the apartments, on the street. We never had any problem finding parking. The apartments are spacious, comfortable, with fabulous views out over the valley. It's a five minute walk to some of the best restaurants, and about a 7 minute walk to the central piazza. In my experience, their website gives accurate photos and descriptions of the apartments. The black tea apartment had a full kitchen, washer in the bathroom, comfy bed and actually comfy pull-out sofa. We were last there in August 2017, but didn't need A/C because of the thick walls that kept the rooms cool, and the fans that were provided.