Suggestions for hill towns to visit

I won't name specific towns because they're all great and everybody has multiple favorites. Hard to go wrong. All the well known (and even unknown) towns are terrific.

My advice is more basic:
I'd spend all four days at one place, rather than packing up and moving on after a day or two. Tuscany is a small enough area that you can drive daily from one base camp to see different places. All the towns in your area will be great. There's no need to travel all over Tuscany/Umbria so you don't miss the two or three obvious winners here. They are all winners.

Stay at an agriturismo (on a farm in the countryside), or at least do NOT say inside a town of several thousand population. The reason for this is the difficulty of parking and driving into/out of the city daily to see the other hill towns.

If you stay downtown in one of the hill towns:
If your hotel has parking, you still have the difficult time of driving into/out of the town daily, with traffic, narrow streets, traffic, one-way streets all seeming to go the wrong way, traffic, getting lost, etc.

If your hotel does NOT have parking, you end up having to park in a lot at the edge of town, then walk or take a cab to the car each time you want to use it. That may be fine first thing in the morning when you're rested, but you'll dread that extra hike each evening when you're tired from a day of sightseeing. And you WILL feel tired by late afternoon. Even if you just drive 30 minutes then spend the day taking it easy as you explore a hill town, even on a cool day, then drive back to your lodging late afternoon, you'll be tired.

If you stay outside of town, you can have easy parking right by your lodging, and it's easy to jump in the car and go for your daily visits.

Makes sense,. Any area, and or agriturismo to reccomend?

Any and all of the towns are wonderful to visit. If you have a car...just go for it, drive and discover. Why go where everyone tells you to go? You might find some wonderful place where NO ONE is carrying a Blue guide book! Get off the beaten path!

Have a wonderful time. Tuscany is beautiful. Having been to Tuscany, Umbria, Piedmont, Veneto and other regions....Tuscany is one of the most beautiful (but don't tell the people of Umbria that I said that!)

If you really need a recommendation: SG is great, Orvieto good (you are right in seeing these) Pienza, Montalcino, Todi, Assisi. There are just so many!!

"Makes sense,. Any area, and or agriturismo to reccomend?"

We traveled all over Umbria and Tuscany in our recent 3 weeks in Italy.

Here's my own recommendation for four days there (which usually turns out to be 3 days and 4 nights):

I'd stay all 4 nights at Agriturismo San Gallo, right on the edge of the hill of Montepulciano. Of all the places we stayed in 3 weeks in Italy, our three nights here were our favorites. Of course, there are dozens of similar places in Tuscany, many as good, probably many even better. This is just were we stayed, and loved it.

Day 1 I'd see Montepulciano, just 1 mile from the agriturismo.

Day 2 I'd see Monticchiello in the morning and Pienza in the afternoon. Be sure to take the Piccolomini Palace tour.

Day 3 I'd see Cortona.

If you do have a 4th day, come up with something on your own after you get there and see what it's like. October should be a wonderful time to be there, after the heat of summer is gone.

We've stayed in hilltowns thru the area, sometimes with parking at the hotel and sometimes not. If you're parking in the hilltown you definitely want a small car! It wasn't that much trouble to park outside the gates, but an agriturismo does sound nice. However I felt that by staying in a hilltown it was ours at nite. The day-trippers are gone by 7pm or so, and as we walked around old ladies were wishing us "buona passegiatta" amd the town was quiet. Nothing like dinner in a restaurant overlooking the valley as the day draws to a close, and walking around after dark it felt not that much different than it might have 400 years ago.

As for pace, we didn't feel rushed visiting 1 in the morning, having lunch, and ending the day at a 2nd one. Just pick a pair that are in the same general vicinity. Actually it was fun driving between them, too, because the countryside is pretty and you can see the hilltown white on the hillside in the distance as you come closer.

This is a frequently asked question here, and here are some of those prior discussions addressing your question

click here

Hi Jeff,

Since you will be in this Region I just had to recommend a great winery you could visit near the town of Greve (which is in the Chianti Region).

It was called Castello di Verrazzano: http://www.verrazzano.com/ . I know that they had rooms you could rent there as well if you are still looking for a place. It is at the top of this huge hill among the vineyards.

Even if you don't stay there it's definitely worth the stop for one of their wine tours. It was the highlight of our entire trip in Italy.

We did the lunch tour (the Chianti Tradition). It was about an hour tour of the grounds. Then you sat on this terrace overlooking the vineyards for lunch. You sampled 4 bottles of wine and everyone had a huge plate of meats, cheese, and bread. The best part was after they poured the wine they left the bottles for the table to finish. Plus you also sample a Dessert wine along with a Balsamic Vinaigrette.

The grounds were absolutely beautiful there and the staff was so helpful and very kind honest people.

next time we go to Italy I would love to stay there or at least in that region.

Have a great trip!

Cortona and Gubbio are nice stops to visit

Assisi is beautiful, but perhaps too far to drive.

Siena! Definitely Siena!

What about Volterra. Not so touristy.

"What about Volterra. Not so touristy."

That's what they say about Volterra, but it was certainly full of bus loads of tourists when we were there recently. I wonder if Volterra is now on the cruise ship excursion schedule.