Pienza vs Montalcino as a base?

We love Montalcino so would lean that way. Great restaurants and unbeatable wine.

Who knows about weather? We are facing freezing temps in the Val Gardena this weekend, but it is expected to warm up next week again. We were cold in Amsterdam last week. It could be warm in late October! Layers and a rain jacket are the key. I would pack a fleece layer at that time of year.

Pienza. I love Brunello but i found little of interest in Montelcino otherwise.

Another vote for charming Pienza.

I enjoyed staying in Montalcino and unfortunately ran out of time for Pienza. Rick's guidebook suggests that restaurants in Pienza are "more expensive and less reliable" than those in neighboring areas. But I suppose that's not definitive and he does recommend two there.

Near Montalcino is a charming 12th-century abbey worth visiting, Abbazia di Sant'Antonio. In the nearby village of Castelnuovo dell'Abate is a decent restaurant with a terrace for outdoor dining. Great for lunch.

Pienza is very small. I'd have been bored staying there. I stayed in Montalcino with a car and thought is was a great base for exploring the area. There is one non-ZTL route through town, but it's best to just park in the lots at the edge of town and walk to the apartment. Distances aren't long.

We stayed in Pienza for 3 nights.

It is flat which means easy walking. The town is storybook pretty, very charming, extremely well-kept, main area of town is car free and the views from town over the countryside are fantastic with multiple lookout areas a short stroll away.

Shops there are quite limited but good.
Restaurants are quite limited, good but not many options at all, in peak times places will be booked so reservations are needed since there are only a few, in late Oct probably not an issue.
We had trouble getting a table a couple of times, so ate at the hotel restaurant which did have excellent food but was pricey. Il chiostro was the hotel and is right in the heart of town.

I think Pienza is better situated than Montalcino for a base when day tripping with a car - it sits in the middle of Montalcino and Montepulciano, it is also closer to the very pretty Val D'Orcia farmland area, Madonna Church, Gladiator Road and other sites ; there are a handful of famous picture spots that lie between Pienza and San Quirico which is a very small distance.
Getting too and from your car at the main lot is a very easy walk (down one hill / paved ramp) which is really nice at night and doesn't add much to your travel times. It is also free to park there.
On the downside the main lot is extremely small, won't fill up at night but midday it will and if you are returning to town midday you may have to park much further away on side streets.

Pienza only gets crowded with tourists during the midday hours, it is really charming at night once they leave. The crowds are actually small even at peak times, it is just such a small area, it doesn't take many people to fill up the streets. After sunset the locals come out and their children play in the main piazza.

I cannot stress to you how small it is though, like 3 streets each 100 yards long small. You will cover every inch of it in a day, so by 4 nights you will either love the fact you know the town like the back of your hand or feel bored. You may also be disappointed by the lack of restaurants in town. You won't tire of the views though and if planning busy days driving it is a great base.
We loved the town,, stayed 3 nights and thought that was the perfect amount of time.

I now feel like we saw all of it though, so a return trip I would be more likely to stay in much larger Montepulcino personally.

Very awesome responses. Thanks everyone!

We decided to book the apartment in Pienza, I cannot wait.
Does anyone have any spots in town that we should not miss? Restaurants or day trips? We will probably cook a few nights and eat out a few nights and lunches.

We definitely want to visit the abbey in Montalcino. I looked up the hot spings in case we have a cold day.

We live in the mountains in Colorado so we are big hikers, if anyone has any recommendations for hikes I would love that.

Ask locally about hiking. There are some books around but they go out-of-date quickly as things change. A few years ago we hiked from Montalcino to the abbey I mentioned. Luckily our B&B host was able to provide updated and local insight or we might still be wandering. I suggest you pick up a book that includes hikes in the area and once you have settled on some, ask locally how the routes are.

out of Pienza (which would have been my recommendation!), make sure to go to Monticchiello to eat at La Porta. It was highly recommended by a fellow poster here (Julie from Wichita, see if you can find the trip report from their spring trip), and it was a wonderful wonderful place. Probably about a 20- to 25-minute drive from Pienza.

I also recommend a visit to the Abbazia di Sant'Antimo mentioned above on the far side of Montalcino at Castelnuovo de l'Abbate. The whole area is gorgeous so enjoy your days exploring.

So glad you chose Pienza. We stayed there about seven or eight years ago in September despite Rick's eh review. Loved it. One of our best ever choices. Perfect for day trips - including Cortona - and then back at night for super easy walks to dinner.