Assisi or Cortona?

I would not choose Cortona, I find that Montepulciano is actually nicer (thanks to the surrounding landscape - the actual towns are relatively similar).

So, given that alternative, I would choose Assisi. Perugia and Orvieto would also be good choices. Do you have a car? Otherwise daytrips will be quite time-consuming.

Thanks balso.

We will have a car. We will actually be visiting Orvieto for a day as well.

We were in Assisi about a week ago, when it was hot beyond belief. Visiting the Basilica di San Francesco (St. Francis) is a very moving experience. Other than a small central area, so many streets are going up or down a hill and might be a challenge for anyone with mobility issues. Driving means lots of small narrow one-way streets (we did not have a car).

Cortona is a pleasant hilltop town; some nice churches, a museum displaying Etruscan artifacts, shops and restaurants. Also Frances Mayes’ home Brimasole which starred in her book and subsequent movie - you can do a walk-by of it.

Assisi has a lot more to offer with the two Basilicas associated with St Francis. Santa Maria del Angeli at the base of the hill is a large baroque church built around a small chapel supposedly built by St. Francis and of course the large and beautifully frescoed Basilica where he is buried. Many other ancient and important churches in the town, including one built within the shell of a Roman temple dedicated to Minerva.

Check parking arrangements in Assisi before driving there. I believe there are one or more large parking garages. I recall some escalator assistance for getting to or at least near the top of the town--well away from the highly touristy area right around the basilica. I highly recommend seeing that lovely historic area, where you may well not see any other tourists for blocks at a time.

Assisi is a very moving experience on several levels. And Assisi itself is on several levels (it is built on the side of a mountain). The art found in the churches (don't just go to the main 2 or 3) is powerful as art, religious expression, and cultural history. Since the 97 earthquake, the restorations have been done with great care. But Assisi isn't just about the 12-13th centuries. Rome was there before and can be visited under the Piazza Comune. Not old enough for you? Try the Etruscans - you can find some evidence of them below the church Santa Maria Maggiore. The main residential area is above San Rufino and is worth walking through. Keep going up and you'll find more ancient Roman ruins. Keep going up to the medieval castle, the Rocco.

Assisi during the middle of the day can be filled with tour groups. But they are pretty much gone by late afternoon and the city returns to a peaceful, beautiful, therapeutic, marvel. Two nights is not too much!

Near Orvieto is Bagnoregio ... YouTube this medieval town

I visited both Cortona and Assisi this summer after staying in Montepulciano. I would definitely recommend Assisi. There’s a lot more to see there. The parking was not a problem at all, just follow RS’ advice.

Regarding the Montepulciano area:

https://www.wanderingitaly.com/maps/valdorcia.html

Orvieto there is free parking in the large lot behind the station. Take Bus 1. up to town, the Piazza della Repubblica. The funicular goes only partly up, to Piazza Cahen; handy for walking down the hill for a ride back to the station.

Thank you all for the recommendations! Sounds like Assisi is the best choice

Thanks!

Adam

I have traveled to both cities. Cortona is a small and quite town. I was only there a few hours and enjoyed the vistas and the main piazza.
Assisi is one of my favorite cities. I have spent many days in Assisi. Not only can you visit the Basilicas, St. Francis’ early life sites (birthplace, Chiesa Nuova) but you can travel to the Eremo delle Carceri (he returned to the the Hermitage during his life). You can take a taxi or take the long walk.
Assisi is a great place to visit for their sites but also their food!
Have a great trip!

Thanks spello09!

Assisi is one of my favorite towns in all of Italy. Walking up and down the cobbled street hills of the town......You can just imagine St. Francis walking with you!
Suggestions:
1. The tour buses can ruin the experience. Go either early morning or late afternoon/evening. (The basilica is beautiful at night!)
2. Try to see Santa Maria dei Angeli......In the lower town, outside of the walls. Within this ornate Baroque church, is the 1st little, tiny, humble church that St. Francis built......Right in the middle of the Basilica!
3. Standing on the opposite end of the lawn from the Basilica (facing the Basilica), in the wall that runs along the right side of the lawn, there is a door/gate. Go through that door/gate and begin the downhill hike that transverses the side of the mountain, where St. Francis walked through the woods. It's incredibly serene......A nice break from the crowds.
5. Secret Garden Bar: I'm hesitant to share this, but it's such a surreal, relaxing experience...... Bar Giardino San Lorenzo. You walk through the gate, into a beautiful garden, in full bloom, that overlooks the rooftops and valley below. In the AM, you can order coffee and pastries. Throughout the day, sandwiches, snack foods & drinks are available. My favorite times in the garden are in the am, enjoying a cappucino & pastry, and watching the mist begin to lift from the valley below.......And around 5/6pm, enjoying a glass of wine, while the sun begins to set and the bells from the Basilica are chiming.......Magical!
6. Finally, avoid the touristy restaurants on the main street. There are some wonderful restaurants on the streets that veer off.......both up and down the hill.

Thank you everyone for the suggestions. We ended up going to Assisi and it was one of the highlights of our trip. It was beautiful! And I think we were lucky since there didn’t seem like there were a lot of tourists at all.