We are Seeking Perfect Tuscan Hill Town for Extended Stay

Many will say Lucca, as it has many fans, and especially as it is in proximity to Florence and CT. It would not be my pick, I found it excessively crowded with day trippers and that was well over a decade ago on my first visit, but I’d definitely look in that area.
We need to know your transport plans. If you are sticking to train, it’s very easy to narrow down.

Unless you're committing to having a car for at least some of your stay that will greatly limit your range of choices. Picturesque hilltowns are not generally well served by mass transit and make day tripping difficult.

This is a pretty good guide to towns accessible by rail or rail and bus.
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If you want to go by rail I would suggest Arezzo as only moderately touristy and connected by rail to Florence - the local transit hub - that puts eastern places like Cortona (train and bus) and Lake Trasimeno within reach. Or Siena - very touristy - but well connected by tours, bus and train to the areas around it and Florence as a hub. Both are worth exploring for a couple days on their own, have many good restaurant options and car rental agencies etc.

People choose Lucca because it is on the flat and is connected by rail to towns around it because trains work well on flat land. And while it has its quiet charms it is not a Tuscan hilltown of photo and film like Volterra, Montalcino, Pienza etc.

If you really want the hilltown experience I think Montepulciano is the largest of the famous southern towns because at three weeks I guarantee you will have eaten at every place in a small town at least 3 times by the time you're done. I would choose the largest charming town with the most options and go from there. There is no town perfect situated to allow easy access to northern towns - Volterra - and the southern towns. In the northern area you might look somewhere like Castellina in Chianti which was small but trying hard to get on tourist map when I stayed there many years ago. It is well positioned between Siena and Florence to visit the northern areas.

Buonconvento is really well positioned with bus and train access to Siena and easy car access to the southern towns and a bit far for Greve and the other northern towns but doable. But the town itself is really small so an agriturismo outside could be a good option but is a different trip than you are describing.

Good luck,
=Tod

Lucca is lovely, especially in early morning and evenings. However, it is not a hill town

I'm assuming you'll have a car. Perhaps look further south to Pienza, Montalcino or Montepulciano. Although they may be too small for a week depending on your style.

SAN Casiano dei Bagni …

Consider choosing 2 locations
Staying 3 weeks in one small town could become monotonous, same restaurants etc and the long drives will become tedious

Maybe Lucca or somewhere near for the north/ west and then Montepulciano for south/ east

Consider slotting any over nites in between 2 longer stays so you don’t have double booked lodging
Lucca then CT then Montepulciano for example

Assuming you will have a car for at least part of this trip? Really need one in this area

Wow! Thank you all for the great and very helpful replies. We will have a car. So, transport is not a concern. (At least I can drive on the right side of the road).

Whenever in Europe, we always find ourselves saying “We wish we had more time to do nothing.” But, the advice of three weeks in one spot is well taken. Three weeks of nothing may be too much and three weeks of the same Trattorias may be too little. Lol

We’ll definitely look at your suggestions and consider spitting Tuscany in two. (We’re planning a week in Rome before Tuscany)..

BTW - just returned from a great four week trip to England, (Cotswolds, Lake District and London) after crossing over on the Queen Mary 2. If anyone considering similar, I’m happy to share thoughts.

Thank you so much once more
Scott

What time of year? Does "side trips" mean you'd also stay in Florence, Cinque Terre, and elsewhere for a few nights? Have you already spent some time in Siena?

I’d scope out flight options so you can know what would work most efficiently—half north and half south or half east and half west. I’m basing that on it you’d like to be within day trip distance to CT and Florence.

In Val di Chiana: Cortona or Castiglion Fiorentino or Lucignano
In Val d’Orcia: Montepulciano or Pienza or San Quirico
In Alta (Upper) Val D’Elsa: San Gimignano, Colle Val D’Elsa, Barberino Val D’Elsa, Monteriggioni (very small but quaint)
In Val D’Era: Volterra

“Val” or “Valle” means Valley.
Chiana, Orcia, Elsa, Era, are names of their respective rivers.

Personally I'd pick Siena. It is bigger than Volterra, but that is one of the reasons I'd pick it for 3 weeks. It is large enough that you could spend more time exploring it, and has good public transit connections, and is very central for much of Tuscany. I know you say you will have a car, but it might be nice to be able to hop the train to Florence, Pisa, etc. Or just take a bus and not worry about parking.

Thanks All. Great insights and advice!

Nancys8 - Yes, the original plan was to home base and spend a couple nights away in CT and Florence. We’ve passed on Sienna in the past. Maybe a day trip this time. But, probably too big for us to use as relaxation-central. Looking at September into October 2027 to catch wine and grape harvest activities.

Now leaning toward maybe 7-10 days in Volterra and 7-10 in another town as opposed to camping out the whole time in one town. We just spent five days at a place in the English Lake District surrounded by sheep and little else. I wish we had stayed seven or eight. First and only time in Volterra, we stayed seven nights (one away at Assisi) and I felt cheated that we weren't there longer. So, getting bored is pretty far down our worry list. :)

I know you liked Volterra, but if you've been there before why don't you pick two locations where you haven't been before?
For example the Val d'Orcia could be one location (that is a bit of a drive from anywhere else). Another location could be Cortona, or even Umbria (Assisi, Spello, etc.)

The outlier of all this remains Cinque Terre. How about 7 or 8 days each in a southern and northern base town in Tuscany and then the remaining amount of time on the Ligurian coast - maybe smaller Moneglia or larger Sestri Levante - which will give you access to CT but are probably a better base for a slow stay kind of vacation it sounds like you enjoy. There are many little towns within a few minutes train ride to explore like Chiavari/Lavagna, the ritzier Rapallo.

It seems like you are spoiled for choice, have a great trip,
=Tod

Consider Tarquinia --- medieval center, a field of below-ground Etruscan tombs with lively scenes painted inside, hill town, archeology museum, towers, church with good frescoes, excellent food, city walls (both medieval and Etruscan), almost on the coast (you can see the sea from the town), and much less touristed. We enjoyed staying there a lot. It's in Lazio, just south of the border with Tuscany, less than 3 hours south of Volterra. You could, if you wanted to, return your car in nearby Civitavecchia and take the train to Rome if you are flying out of Rome.

Check out Greve in Chianti. My husband & I stayed there for 3 nights many years ago and were lucky enough to hit it when there was a wine festival in the small town square in early September (unplanned and a great bonus). We had pre-arranged with the agriturismo owner to take a private cooking class one day, which was a highlight of the trip.

Our itinerary began with 2 nights in Venice, followed by 1 night in Bologna, 4 nights in Cinque Terre (Vernazza), 2 nights in Florence, then 3 nights in Greve in Chianti. We took trains until we departed Florence, where we picked up a rental car before heading to Greve in Chianti.

Greve town is very small, and it was a pleasant stroll through the vineyard down to the town and back to where we stayed. I wish we could have stayed longer, because it was so relaxing, not touristy (at least at that time), and the views were breathtaking.

Best of luck in your planning!

We are planning a family trip with 12 total. So we need a house for 2-3 weeks. We are zeroing in on the Lucca because of it's access to trains, Pisa airport, Cinque Terre, and Lucca itself. We expect for some to head out to Florence for an overnight or two as well as Cinque Terre. I love Pienza, but wouldn't stay more than three nights. There are a lot of hills around Lucca with houses. Roads are windy and narrow so getting to and from Lucca by car might be up to 46 minutes. There are so many places that we like and have visited for 3-4 nights each, so this will be different.