Thoughts on Assisi / Tuscan hill towns

Keep your regions straight--Assisi is in Umbria, not Tuscany. Umbria's a whole different game. It's a somewhat wilder, less touristy region, with traditions of its own. Assisi is a beautiful town, but it can get crowded with pilgrims and tourists during the high season.

Do not go to Assisi on Oct.4, the Feast of St. Francis as it will be very crowded. Save Assisi for a trip to Umbria; focus on Tuscany which is a very large area.
You only want hill towns? Many charming Tuscan villages are not on hills.
Siena, Castellina, Radda, Panzano, Greve,
San Gimignano, Volterra( on a big hill), Pienza, Montepulciano, Cortona

I recently spent 9 days in Tuscany/Umbria with a car. Yes, there is a dividing line between the two regions that goes back to the days of the Etruscan and Umbrian tribes, but for us tourists (and I suspect for many Italians) it's all much of a muchness. In an hour's drive I went in and out of Tuscany and Umbria, according to the road signs. Had they not been there, I wouldn't have known.

First, don't believe GPS on driving times. It always takes longer. Assisi is great on a sunny day. I recommend parking in the John Paul II parking lot. From there it's a short easy uphill walk to the Basilica, with its wonderful frescoes (binoculars are very helpful). Then its another easy uphill walk to the center and on to Santa Chiara church (the founder of the Poor Clares). There are other interesting sights and nice shops to pick up gifts and souvenirs, some are very tasteful, nothing much that's tacky.

I liked Montepulciano, loved Spello and Spoleto (also in Umbria). Consider a day on Lake Trasimeno - maybe take the ferry to the island, have dinner in Castiglione del Lago, very close to Montecchiello, but also Umbria, I believe.

Damn, I'm already being an ignorant North American tourist and I haven't even left yet. I apologize for my careless mistake. I've never been to the Tuscany/Umbria region and am just now learning the unique and wonderful differences.

Great advice on Oct 4 as that is the literal day we arrive. Will avoid that time.

I suppose I meant Tuscan towns. "Hill," just rolled off the fingers.

Once we actually arrive, I suppose I'll look back on some of my posts on here and do a face palm.

Thanks for the helpful advice Chani and everyone. I really appreciate it.

Ha! Sorry, John. The Tuscan-Umbrian rivalry is like New York vs. New Jersey, or Vermont vs. New Hampshire: There are more similarities than differences, but we keep it going for fun. Plus Umbrians are lower-key and think that Tuscans just hog the limelight. And southern Tuscany is almost overrun with Brits, so much that it's nicknamed "Chiantishire."

Should you wander into Umbria, I'd say yes to a day on the lake. Take a morning ferry to Isola Maggiore from Tuoro sul Lago. Hike around the island--you can't get lost--and then have lunch in the garden at Da Sauro. Perugia's a cool college town, worth an overnight. I like Gubbio, Spoleto, Spello and, for reasons totally unrelated to "sights," Gualdo Tadino. And, of course, Assisi. Don't overlook nature walks either. You can duck inside the door on the right in the wall outside Assisi's basilica and take a hike in St. Francis' Woods--Il Bosco di San Francesco. It's a beautiful, tranquil place run by FAI, an environmental group. In general, there are lots of great mountain, lake, and forest hikes in Umbria. And since it's Italy, a good drink or coffee or meal is just around the corner after your hike.

haha thanks Apaonita. I totally get it. That all sounds amazing and we'll definitely be checking it out. We're avid hikers and lovers of the great outdoors which is why we planned our time in this region for beautiful October.

You are in Monticchiello for 10 days. That means that you have at least 9 days at your disposal to take day trips. I know the choices are many, but this is the list of the most visited destinations within 90 min from where you are (with the exception of maybe Spoleto, which is maybe 1h45m away). I wouldn't miss any from this list, I don't care if they are not in the same region. I separated them by separate trips, since some they can be paired in the same trip.

TRIP 1: Pienza (Toscana); Montepulciano (Toscana)

TRIP 2: Siena (Toscana)

TRIP 3: San Gimignano (Toscana); Monteriggioni (Toscana)

TRIP 4: Chianti Hills (Toscana) [this could be even be added to trip 3, if you like)

TRIP 5: Assisi (Umbria); Spello (Umbria) [possibly could add Spoleto (Umbria), but maybe too much for a day]

TRIP 6: Orvieto (Umbria); Civita di Bagnoregio (Lazio)

John -
Whatever towns you choose, and the recommendations from others are very good, you will have the time of your life. Both Tuscany and Umbria are unbelievably beautiful. DO make reservations for dinner in Osteria La Porta in Montichiello, as it is one of the best restaurants in Tuscany IMHO. It's so good you might want to go twice.

We’ve spent many vacations in Tuscany and Umbria and of all the wonderful towns we’ve stayed in or visited, Assissi is our absolute favorite. It’s beyond charming and wonderful. If there’s a way to make it work, i would.

I've been to all the places Roberto mentioned and the one I would cross off the list is Spoleto - not exactly sure why I didn't love it.

Wow everyone, just stepped out for a walk and boom, so many great suggestions!!! Roberto, can you plan all our trips?? We're also spending a week in Florence before that so.. let me know your don't miss things there too. But seriously, your trip list has already been put in our Big Ass 25th Anniversary email folder (it's a working title) and I can't wait!! What about Cortona? I've heard that's another great town.
Susan - thanks, we're sold! We'll just avoid October 4th...

Yes. I forgot Cortona (and many others), another very popular destination. Less than one hour away from Monticchiello.
Montalcino (the land of the Brunello wine) is also a very popular destination (only 30 min away).

Here you can find a list of lesser known villages that make the list of the Borghi Piu belli d'Italia:
https://borghipiubelliditalia.it/borghi/
This is another website I use. They used to have an English version, but can't find it right now. Maybe you can use Google.
https://www.borghiditoscana.net/category/borghi/

One practical suggestion I have, based on recent experience is to research where to park the car in each town - they are all hilltops with the dreaded ZTL's. And pay careful attention to how you get from the car to the town, so you can find the car at the end of your visit (don't ask what happened 🤣). Most have multiple parking lots outside the walls/ZTL's. Expect to do a lot of up-and-down walking.

If it were me, I would drive to Assisi for the day (1h 45m). The number one hill town in my opinion is Montepulciano (15-minutes). The other three are Volterra (2h) and Pienza’s old town (15-minutes) and Cortona (1h).

Assisi is well worth the visit, IMHO and if you're interested in art history, it's thrilling to see the Giotto frescoes in the basilica of San Francesco.

We stayed in Umbria for a week 11 years ago and loved our dinner at Agriturismo Bellona so much that we went back a second time.

Thanks Rebecca! Great suggestions. We do love our art and good food!!

In Rick Steves Tuscany show, he went to an Osteria in Montepulciano but he never gave the name of it? Where can I find it out?

329471-

You’ll get more responses to your question if you post it in its own thread with a descriptive subject line

Rick probably includes the place you are looking for in his list of restaurants in his Tuscany guide book

We have just finished a 5-night/ 6-day trip to Tuscan/ Umbrian hill towns closely following Rick's suggestions in his Italy guidebook.

San Gimignano - Montepulciano x2 - Assisi - Orvieto

They are all interesting and different (and at the same time similar).

Assisi was our favorite - it is looking absolutely beautiful at the moment. Spotlessly clean and flowers everywhere. It is also perhaps the best lit urban space I have ever visited at night. Our photos look stunning day and night.

Also Rick has two audio tours for Assisi on his free Audio Europe app.

One practical suggestion I have, based on recent experience is to research where to park the car in each town - they are all hilltops with the dreaded ZTL's.

ZTLs are dreaded only by those who don't do their homework before leaving or are inattentive. I was spooked by all the posts about ZTLs before we went. Luckily I did some reading and decided that there was a lot of hyperbole.

What we found was ZTLs, especially in hill towns are well marked and easily avoided. A good rule of thumb is to assume anywhere within the walls of a hill town is a ZTL, though I can't think of a single hill town where there wasn't plenty of clear signage.

Larger cities, such as Florence, Rome and Siena might be a little more confusing. The only city we drove in was Siena. Trying to follow GPS instead of using a map and our eyeballs almost got us into trouble, but instinct and common sense saved the day.

Tuscany and Umbria are magical places. Each village has their special charm. Radda and Volterra stand out for me. Also, we loved The Abbey of Monte Oliveto Maggiore. We visited in the late afternoon, had an early dinner and returned for vespers. Vespers are celebrated with Gregorian chant. I was just the monks, one lady from a nearby village and us. We were encouraged to participate in the responses. It was a very moving service.

We day-tripped to Assisi from Spello last month. Short train ride and quick bus to the top, but it was offensively over-touristed. How many plastic trinket shops does a town need?

We did not find Assissi touristy at all.
Just charming, beautiful, interesting, fun and every step you take is a Kodak moment. We’ve stayed in Montepulciano and liked it but far prefer Assissi.

Thanks, everyone! Assisi sounds amazing and we'll def go for the day! Might even go back. :)

Was just in Montichiellio Tuesday evening and had dinner at Daria. It was very nice and hope to go back to the town again. It will be a nuce base for your trip. My don’t miss is Volterra. Did the Volterra Walking Tour today and really got a better understanding of the history from the Etruscans and Romans to the impact of WWII. I didn’t learn as much the first two visits… I second the comment that don’t expect driving times to be what they are in the apps - everything takes longer and allow time to find parking. It’s really easy to avoid the ZTLs. Have been using Waze and it’s been accurate so far for all towns big and small. Very helpful are the warnings it gives for the speed cameras and red light cameras (lights turn red in the tiniest of towns that you wouldn’t even expect a light and they stay red for quite some time). This is the first trip in which I have seen Italian drivers at the speed limit in some areas and slamming on the brakes in others. One suggestion posted by Cameron Hewitt was to bring a phone vent clip. Had never thought of it and it’s the best accessory we brought. Enjoy your trip!

Thanks for the great info JMF. Good idea with getting Waze. We'll def do that. Yes, Volterra is on our list as are many others -esp Assisi. A fan favourite on here. We chose Montichiello as a base because of the stunning Air BnB we found there. :)

CNN has a series: Stanley Tucci: Searching for Italy and last week Season 2, Episode 3 was Umbria including Assisi and this year, Rick Steves' shows on PBS had a few shows on Italy that provide a good overview of northern Italy and last year covered Rome.
I record these as we're going to Rome, Umbria and the Lake in Octoberbfor 4 weeks and they give me an indication of what to look for and try.

Cortona is definitely worth a stop. Very charming, lovely town. Roberto had some great suggestions.

Hi John,
If you don't mind, would you tell me the name of the agriturismo in Montichiello. We will be going to Tuscany and Umbria in June and I have places reserved but I am always one for writing down the names of good places for future trips. I'd love to google it as it sounds amazing.