OK Umbria Lovers, I need your guidance now!

One one trip we stayed 10 nights in an apartment in lovely Spello and easily daytripped by car to most of the places on your list. I prefer driving to unpacking.

I have only visited Urbino and that was this September. While it was ok it paled in comparison to Assisi.
Also Deruta was so- so imo. If you need info on Puglia was there in Sept.

Oh, where to begin! We really enjoyed this part of Italy. A few ideas for you:

Bologna: Ride the city bus up to Santuario di San Luca (there's also a "Tourist Train" but the city bus ride is enjoyable; the driver and riders are friendly and helpful). Enjoy the views and the basilica, then walk back to Bologna (downhill!) through about 2.25 miles of porticos--the longest in the world. There are many viewpoints along the way.

Gubbio: Ride the Funivia Colle Eletto to Sant' Ubaldo. You can walk back down to Gubbio on a well-maintained path. There's a bar/cafe with outdoor terrace not far from the Sant' Ubaldo basilica where we enjoyed a simple yet delicious lunch--and the view is stunning!

Spello: Walk through the historic center. Visit the Villa dei Mosaici di Spello.

Something I really enjoyed was just walking through the historic centers of each town we visited. There were surprises--churches, architecture, artisans, museums, restaurants, etc.--everywhere we looked.

When planning for travel in Umbria I found the tourism websites for each city to be quite helpful. Many have some sort of a "City Pass" available; often the Pass will pay for itself after visiting only one or two included attractions.

Hola Lorencito! I'm so glad to hear you've got Italian travel plans! Sadly, I have no insights for you, you've already been to all the places I've been to. What are your dates? (I'm thinking about a NoCal visit in May . . . )

We are planning a week in Umbria and plan to visit Orvieto as well as many of the places you listed. We were planning one night in Orvieto, then moving up to either Perugia or Assisi as a base for doing day trips to Spoleto, Gubbio, Spello and more.

We had a lovely, although moderately strenuous, hike near Spello. Take a look here for details.

Hi Larry,
Bevagna is a lesser-known town that makes for an excellent base, with any number of compelling daytrips somewhat nearby (we did all of them using a combo of public transport and taxis).
A great-value splurge in Umbria is the actual Abbazia S. Pietro in valle: fantastic views, the best breakfast and reasonable price point throughout. Atmosphere. Some exceptional hiking nearby.
Maybe do Montefalco brunch on a Saturday (reserve @L'Alchemista) to take in the weekly Flower market for added value.
Spoleto is a must. Spello's Cafe Propenzio has an awesome wine list with very good, reasonably-priced food.
Trevi is also a sleepy, not-as-well-known town in the area. It'd also give you the chance to check out Fonti di Clitunno.
Castelluccio seems to be 'open' to the extent that drivers can arrive for a look at the surrounding Sibillini park. Those lucky ones who have timed their morning arrival to include a thermal inversion will never forget it--world-class photo-op.
Good luck!
I am done. The end.

I second Ruth's suggestion - we also stayed in an apartment in Spello for 5 nights (through VRBO.com) and took day trips to all the places you mentioned. It was so nice to come back to Spello each day after sightseeing - the town is beautiful, especially when lit up at night, and there are several good restaurants to choose from, as well as an interesting little market. You might want to spend more time in a couple of towns and drive to the others to avoid packing/unpacking and to get a chance to really get to know the small towns you are staying in.

Assisi deserves more than a day trip.
There are pilgrims and other visitors there from ALL OVER who visit just during the day.

Even though that did not bother me and I found Assisi to be a peaceful place, especially in the evening when the hordes have departed. (I am not very religious, I just had a sense of peace in the three days I was there)

I don't know if it would have felt as peaceful had I rushed through it in part of one day.

I can add an enthusiastic plus to Bevagna as a charming small town, as well as Bettona, not too far away from it.Both are quite convenient to Assisi & perugia & maybe 30 min. from Lago Trasimene. In fact, I spent a week in a wonderful apt. in Bettona, with free parking maybe 100m. away, & used it as a base to visit much of Umbria. Casa Foresti in Bettona is well worth a look, on Airbnb.

I have stayed in Perugia and I loved this place. https://www.booking.com/hotel/it/garden-house-perugia.html?aid=1213432;label=seogooglelocal-link-imagesaow-hotel-2623243_grp-3_gendate-20191016;utm_source=seogooglelocal;utm_medium=photo;utm_term=hotel-2623243_photo-110087840
It is in the historic district. You park your car at the bottom of the town (not expensive) and take an escalator to the top. Easily walkable and you are in the center, but off on a side street, very quiet and nice gardens.

https://community.ricksteves.com/travel-forum/italy/cortona-worth-it

so many good suggestions I hate to chime in too, but I just have to. You mention wine. Look into Montefalco. We went there in the fall of 2016 just for the Sagrantino. I was worried that my husband had heightened my expectations too much and that we'd find fine, but not spectacular, wines. Or that it would be priced out of our budget. I couldn't have been more wrong, or more delightfully surprised. We had such a fun experience in a less touristed part of Umbria and the wines knocked my socks off. And I had to poker-face my smile (unsuccessfully) when they told us the prices of the wines, both the Sagrantino (red) and the whites (I can't remember....). So, Montefalco gets my vote. And it's a lovely village with a couple of very nice restaurants. And a wine shop :)
For a stay, we stayed at Castello di Petroia. I don't recall the prices, but it was a very nice stay.
Have a great trip!

I would get bored in Bologna for 5 days.
would rather put one or two more days in Umbria and go to Ferrara instead.