Where to go in Umbria

Assisi to Spello- You can see these towns from the other one across the valley and up the hillsides. I think it would be a challenging walk so I would drive there. On your second day, visit the charming villages of Montefalco and Bevagna, not far from Spello.There are , in my opinion, more interesting places to visit than those you list Todi. etc. We have been to all of them. Orvieto is a nice stop en route to Rome by car or train.
I would definitely have a car in Assisi and not in Perugia. Parking is a real challenge in Perugia. We got a pricey ZTL violation ticket when we mad a slight turn when entering their public garage built into the hillside. Perugia is way up on top of large hill..
No driving in Venice; the roads are replaced by canals. There is a parking area right before Venice in Piazzale Roma..Taking the train from Florence is best.

Suki- we weren't planning to have car in Perugia-just to rent car in Perugia near train station and leave.

We aren't going to Rome so can't see Orvieto on the way. We had considered staying two days in Orvieto and then three in Assisi but the advice I got (and I think you were one poster) was to not move.

I recall you have spent considerable time in Umbria. What places would you suggest visiting in the time we have if there are more charming choices than the ones I am considering. Everything sounds good when I read about it!

Spello, Montefalco, Bevegna.
Assisi is beautiful but larger.

A couple of ideas for you:

In 2016, I spent a week alone in Todi and loved it. I had an apartment at the bottom of the town, would walk up to the top to find a place for dinner, and as I would stroll down the old ramparts, families of all ages would just be walking up for their dinner after 9:00 pm. It's big enough to have lots to do and see, not so big that you can't do it all. From Todi, I did day trips to Spello, Amelia, Deruta, Bevagna, Orvieto, Carsulae (Roman ruins, not a town) and a few others I'd have to look up. All were wonderful. I never made it to Assisi.

The next week we rented a gorgeous villa in San Gemini, also a beautiful but smaller town. Maybe worth a drop-in, just because it's very back-door. We had a killer dinner in an old stone restaurant with a huge open fireplace full of grilling meats. That week, I took my friends back to Orvieto, which was one of our favourite days that week. A second trip to Carsulae was also a hit with my friends. It was once a bustling Roman market town, then lost for centuries. There's rarely anyone on the site except archeologists but it's great to wander through. One friend and I made the trek to Civita di Bagnoregio another day. I found it interesting but a bit eerie with no town life beyond tourists and those who provide services to them. I wouldn't go back.

Today, Elizabeth Minchilli posted on Facebook about a new place in Umbria she'd never been - Rasiglia - and it looks amazing. If you have Facebook, look up her post. The photography was incredible. It's on my list now.

As far as wineries, I'd strongly recommend a van tour with Gusto Wine Tours. We had a wonderful day out with Mark doing the driving and story-telling, to small wineries he had found, and a fabulous private lunch. I'd do it again in a minute, their tours are very well run, lots of fun, and he is so informative. (No connection other than a customer in 2016)

I second your choice of a wine tour especially around Orvieto.

Another thing about Perugia is the Perugina Chocolate factory - Where the chocolate Baci originated. There is a great movie about its founder from 2016 called Luisa Spagnoli. She was one of the first women entrepreneurs in Italy, bucked the standard chocolate "cartel" from the north and was one of the first to take her workers seriously offering them benefits, etc. Definitely worth watching even if you don't decide to do a tour as it shows wonderful scenes of Umbria.

We can second the idea of a day trip to Rasiglia, a town of beautiful waters. The Carsulae archaeological park was also interesting and nearly deserted.

In March, my husband and I spent five nights in Assisi. We spent arrival day and the first full day in Assisi, visiting the Archaeological Museum, Basilica of San Francesco, and most (if not all!) of the other churches that were open. We found the RS Audio Tours of San Francesco and the Walking Tour helped make our visit more meaningful. (During our stay we usually returned to Assisi in time for dinner and for more walking and exploring.)

On the second full day we took the bus to the Assisi train station, then the train to Perugia. A car rental office is right at the station (we rented through Auto Europe); be sure to check lunch closure hours. The rental agent let us leave the car parked in the rental lot while we took the mini metro to and from Perugia's historic center. We stayed several hours, exploring and stopping for lunch. The TI in Perugia provided a very helpful map and guide to the city. Then we drove to the Perugina Chocolate Factory for a tour. I believe this was the day we made it back in time to visit Santa Maria degli Angeli.

Day three was a leisurely drive to Gubbio. We drove the back roads (be sure to have a good map)! I used a variety of guide books from our public library for planning. There's a bar/cafe at the top of the funicular; we enjoyed tasty piadina and an incredible view here before walking back down to the town (the paths are wide and well-maintained). On our last full day we visited Spello, Montefalco, and Bevagna. We could easily have spent more time here! If you are interested in wine, you will want to research Montefalco.

On departure day it was easy to drop the car at the Perugia station, then catch the train to our next destination. You will want to check with your hotel in Assisi regarding parking as it is somewhat limited. There are many other towns that you could explore in Umbria; I found Lonely Planet and DK guide books to help me with more detailed planning. Have a wonderful trip!

We were staying in Montepulciano, when we asked about that big lake to the East. The waitress told us it was Lake Trasimeno. On the other side of it is Perugia. Once my wife heard that, she had to go to the Perugia Chocolate factory for a tour. On our way back to Tuscany, we stopped for lunch on the lake (forgot the name of the town) and then drove to Cortona for a few hours. That is a cute town where "Under the Tuscan Sun" was filmed. So any of those 3 things might be of interest. Have fun!!!

So many good ideas! Five nights sounds like a lot of time until I see how many options there are--many of places I have never heard of! I did find a Telegraph article on Spello, Montefalco, and Bevegna. I was only familiar with Spello of the trio.

And a chocolate factory!

I am certainly glad to hear my plan of renting and returning a car in Perugia worked for another poster.

And I wondered about visiting a deserted city and think I will take Cita di Bannoregio of my list of possibilities. You all have given more than I can possibly visit as it is!

And I agree getting some specialized guidebooks would help me.

For we public transportation people, the best way to get between Spello and Assisi is by bus. The bus stops are closer to the sights than the train stations in those two towns.