Your top three Tuscan hill towns, and why

Montepulciano, Pienza and San Quirico

Thank you, I'll check them out.

We based in Pienza last trip and loved it
Another favorite to visit is Bagno Vignoni

Pienza as a base was great-easy to come and go with a car. Quiet at night, hotel with easy onsite parking

Look further southwest, in the Super Tuscan wine region around Bolgheri. Base yourself in Castagneto Carducci, as we’ve done in early October of the last two years. Actually, we’ve stayed both times in the valley just below that town, at one of the two apartments at Chicca’s house, where she also has been teaching cooking classes for years. Check out https://cookingintuscany.cc/casa-toscana/ . She also conducts wine tours, or can suggest places to visit on your own. Besides Castagneto Carducci, there’s tiny but wonderful Bolgheri, and Bibbona, with the outstanding restaurant Io Cucino. There are other potential hill towns south of there, including Massa Marittima, which we really enjoyed. The whole area is actually very close to the Mediterranean coast, and the town Donoratico (with a train connection and potential car rental option) offers beach access, but also a worthwhile farmer’s market, as does Cecina, although neither of those are hill towns.

Also, it sounds like you’ve not visited Orvieto, one of Rick’s key hill towns between Rome and Siena. Technically, though, it’s in Umbria, not Tuscany. If you ventured into Umbria instead, Spoleto was a good base for us (parking below town, escalator ramps underground to get up into town), but close to Spello and even Assisi. The former is festooned with colorful floral displays by homeowners’ front doors, and the latter is a major St. Francis pilgrimage site, but the traffic is unfriendly for pedestrians and sidewalks are virtually non-existent.

Any of the ones below.

https://borghipiubelliditalia.it/en/toscana/
https://www.borghiditoscana.net/en/

Montepulciano, Lucca, San Gimignano

I appreciate the detail of your OP, because the question is a very personal one. The fact that you liked Siena and Lucca (which are both very nice) says that you might not consider a smaller town worth the stop. You don't say if you will have a car. I just don't find Siena, Lucca, or Orvieto to be "typical" Tuscan Hill Towns.

Cortona-for the art museum, with some real treasures. Kind of small, hard to find a parking space, but very pretty.

Orvieto-very crowded and touristy, but high-yield, a full day out. Good train from Rome

Castiglione del Lago - Not a typical hill town and very flat, but a real "local" place, with a vast lake and a public beach. Good food was reported to me, but we had a reservation at nearby Aviognesi Winery. Pretty large, and relatively quiet. Town museum, check hours.

Sounds like your tastes are similar to ours so:
Base in Cortona and visit Arezzo, Pienza, and Asciano-Abbazia Monteoliveto , latter especially for the road through the countryside and views. We were based in Sinalunga but just because it was good for the logistics, and we found a place last-minute. Nothing much to see there.
https://slowtravelitalyspain.blogspot.com/2020/11/tuscany-september-2020-cortona.html?m=1
https://slowtravelitalyspain.blogspot.com/2020/11/tuscany-september-2020-abbazia-di.html?m=1
Cortona we parked up by the sanctuary, free, and then walked down.

Thanks for the replies. I definitely like smaller towns for a visit, but they wouldn't be my choice for a base. Once I have a base, I might visit a small town in the morning, have lunch, then visit another small town in the afternoon. The time I spend at each place depends on what there is to see. A small town might have sights that take more time (e.g. winery, church, cooking class) or might just be a stroll around to see the place.

I'll plan to visit Orvieto, this is probably a one-night stop (though I try to limit those). I've been there before and thought it was a good stop between Tuscany and Rome. I opened a separate post on suggestions for a good underground tour. We booked a tour through the TI last time, but it was just okay. I think there are better tours.

1.) Siena (most old world feel and charm ; best piazza)
2.) Pienza (the best surrounding countryside views and perfectly manicured and designed town areas ; downside a little too small)
3.) San Gimignano (little mixture of what makes 1 and 2 above ; but the crowds feel worse here)

I thought Montepulciano and San Gimignano were quite similar. Similar size and uphill design, Montepulciano definitely less crowded and more authentic / less touristy but lacked some of the charm and has less to do so I rated San Gimignano just slightly higher. If wine tasting is a part of your plans Montepulciano is perfect for that!

Thanks, I'll have three people in tow, their vision of ideal Tuscany definitely includes wine. Evening meals with a nice view and/or exceptional food also have to be on our list. My wife is an outstanding cook so anything food related suits her. A mutual friend just returned from Sicily. His trip was largely foodie oriented. Three of the four of us enjoy good food, but a meal or cooking class probably wouldn't be the highlight.

I love history so ancient sites are highlights for me. I don't want to exhaust the others with too many museums, cathedrals or ancient sites but want to include some.

Montepulciano, Pienza and San Quirico

I like Christine H's list. You can easily see all three in a day taking the beautiful drive that starts in Montepulciano, passes through Pienza and then on to San Quirico. The area is called the Val d'Orcia. Continuing on the same road, Montalcino is our favorite. Not only a terrific vinicultural area (Brunello di Montalcino anyone?), but a charming town that is very quiet at night with lovely restaurants. The enoteca scene is fantastic for wine tasting without driving.

While not towns in and of themselves, down the road from Montalcino is the Abbey of Sant'Antimo, from the 12th Century and the Abbey at Monte Oliveto Maggiore is about a half-hour away as well. The monks at that latter make wine, honey, and olive oil (among other things) which are available for purchase. The grounds are lovely. (Rick Steves has both described in his guide book.) At either abbey, watch the clock as I believe they both close from 12:30-14:30. (I didn't look it up but recall from our visits.)

A very particular place is Monteriggioni, one of the best preserved medieval towns in Italy with walkable fortified walls. Not a place to base, for certain, but a worthy stop.

Thanks for the detail Laurel. I'm plotting these on Google Maps, looking at photos and deciding which area to be in. Right now I'm leaning toward the Pienza/Montepulciano area but there are a ton of beautiful little hill towns all over the region. Can't visit them all.

Orvieto, Cortona, Pienza. All uniquely different and wonderful.