My husband and I will be in Tuscany with another couple mid September. We are trying to decide where to base ourselves for 3 nights. We are in our early 60's and are interested in beautiful drives, good food (not fancy), wine tasting, cooking classes, visiting interesting towns and villages. My husband and I spent some time in Monticchiello 10 years ago and it was probably our most favorite destination. We would be very happy to revisit all the places we loved with our friends as they have never been to that region. There is a very special place in Montalcino, Castel Brunello, that has availability. But I'm wondering if Montalcino has as much to offer as Montepulciano, Pienza etc. Villa Poggiano is what we're looking at in Montepulciano. I am wondering if Montalcino would check our boxes as much as we already know Montepulciano does. Our requirements are two bedrooms and two baths, either an apartment or two separate rooms. Thank you

Have you noted the distance between Castel Brunello and the center of Montalcino? It's about 10 kms. Definitely too far to walk if that was your plan, but there are a couple of restaurants in the very near borgo.

The distance between Villa Poggiano and the center of Montepulciano is also too far to walk... at least after dark. About 4 kms. The villa seems to be very much out in the sticks, although I prefer the atmosphere over the Castel Brunello... at least from website photos.

All of the towns you mention have their charms and make lovely destinations, but is where you stay determined by the lodging atmosphere or the town atmospheres? Your choice.

FWIW, I prefer to stay IN the towns and not have to think about driving after dark, looking for parking outside the ZTLs, picking someone to be the designated driver, etc. Staying only three nights would make the drives to and from either lodging to the town centers a bit far for me. But, again, that's me, and a longer stay might make me reconsider.

This is where we have stayed in Montepulciano a couple of times. Only four rooms.

https://locandasanfrancesco.it/?lang=en

Happy planning!

We also stayed at Locanda San Francisco this past March and loved it. They have parking which worked out great as we had a car, just make sure you don’t have a large car as there are some tight turns to negotiate to get to the hotel!

We have also stayed outside of town at Villa Ambra as well as La Bruciata, an agriturismo. We liked both very much although neither was close enough to walk into Montepulciano.

We have found Montepulciano to be a great location to visit Pienza, Cortona and other Tuscan towns.

I prefer Montepuliciano but any of the three would be fine. In terms of walking, 4km is hardly a walk (2+ miles so 40 minutes), but think about walking in the dark a little and of course such things as taxis exist. 10km I might want to use a bicycle.

Thanks for your response. We would actually prefer to stay a little out of town and have plenty of options (towns, villages, restaurants, scenic drives) fairly close by to drive to. Anything near Montepulciano seems to fit that bill as well have stayed in the area before. I was very curious if the Montalcino are has that available as well. A bonus would be a ability to take a taxi if we wanted to do a wine tasting.

Thank you. We have stayed in the Montelpuciano area before and loved it. We are curious as to Montalcino vs Montelpulciano.

We will have a car and will not expect to be walking into town. Are taxis available in that area if we have any wine?

Are taxis available in that area if we have any wine?

I might book, but yes car services and taxis are part of Tuscan life, as are buses.

We loved Montalcino, but it has a far more relaxed vibe than Montepulciano, in my opinion. Therefore, it depends on what you are looking for. We stayed right in Montalcino and parking wasn't the best. The hotel's owner had to find us a parking spot .

Is Montepulciano really that much more steep then say Todi or Urbino? Asking for future reference, as my wife has new knee issues.
I am done. the end

We loved Montepulciano as a home base. Many restaurants and shops to choose from. It is hilly, so keep that in mind if you have ambulatory issues. We were with one other couple and we stayed in the two bedroom/two bath suite at Il Tosco Hotel. The breakfasts daily were absolutely amazing! Convenient for walking through the town and it has designated parking within a 5 minute walk.

Buonconvento and San Quirco d'Oracia are both pretty and flatish

We were in this area with another couple in October 2023 and stayed in Montalcino. We had wanted to stay a place that was smaller and flatter which it was. We loved where we stayed and there was easy parking on site. The joke was on us though because it was in the very back of the town, down a hill, so when walking into town we had to hike up it.

Pros: Small, flat, quiet, loved our hotel and the owner, hotel recommended a fabulous driver who lived in Montalcino, and we ate in some fantastic restaurants

Cons: Shops in town were dominated by wine tasting rooms and overall it was a little too quiet for us

When we arrived on a Friday afternoon, we assumed the restaurant we booked for that night, was walking distance from our hotel, but it was not even close. We asked about getting a taxi, but at the hotel, they said we would never get one on short notice and especially not on a Friday. So you do need to make reservations well in advance for a taxi. Our friend graciously offered to not drink and our evening was great. But we are the types who want to walk to our restaurant in town and not drink and drive. If you are planning to drink at dinner in another town, you need to think through how get there. Italy has very strict about drinking and driving laws.

We hired a driver for 6 hours one day who we requested to take us to San Quirco, Pienza, a restaurant we wanted to go to and Montepulciano. She suggested we skip San Quirco and subbed in Monticchiello. She was fantastic and it was so relaxing to let her pull up to the towns and not worry about parking. We loved all of our stops and she knew the owners of the restaurant so we got a front and center spot. After touring, We thought Montepulciano would be a little too busy for us to stay in but we would love to visit again, and we thought Pienza would be our choice to stay in for the future. We LOVED this lunch! They also have cheese making demonstrations and a farm tour. It was nice having a driver so we could have wine at lunch. Enjoy!
https://podereilcasale.com/en/restaurant/

**Is Montepulciano really that much more steep then say Todi or Urbino? Asking for future reference, as my wife has new knee issues.**

zebec - Montepulciano is steep, but they have a little bus that runs through the town.

Thx KYB.
I am done. the ageing

MP is steep and I would put it on par with Spello (I don't know about Todi or Urbino). Basically the town has 5 levels:

Level 1: outside the city walls -- this is where San Biagio is
Level 2: Bottom of the hill -- main bus depot, main grocery store
Levels 3 and 4: Main corso -- various plateaus but definitely the steepest parts
Level 5: Piazza Grande

There is (was?) a minibus that would do laps of at least levels 2-5 (I forget if San Biagio was on the route).