2 Days in Umbria - Is this Itinerary Feasible?

It’s a lot for that short of time, especially if you want to explore a bit on foot.

By the time you drive from Rome you’ll hav a half-day left, then all of the next day and the morning of a third. What not base yourself in Assisi (beautiful!) and see how much you feel like doing there over a day-and-a-half. You could spend a few hours in Spello as well, maybe a lunch destination. On your way to Montepulciano, you ca go to Orvieto for a couple of hours. It is not exactly on the way, but a feasible detour.

Be aware that driving times in Umbria and Tuscany can be longer than you think based on Google Maps.

As to “must sees” a good guidebook is the best resource. What I want to see and do and what appeals to you will differ greatly.

That is a lot to see on your list. I would focus on Assisi and Spello.

You left out Perugia!

Two days isn't enough for what you plan.

At first I read this as those being the number of days you want to spend in each, and I thought ah, how nice. Then I realized you have two days--I would spend them in Orvieto and its immediate surroundings (circle around Lake Bolsena to Viterbo, Pitigliano--I am sure there are more lovely places). I would find that so much more enjoyable than going through all of those cities in a really limited rush.

I read your post last night and planned to reply this morning, but then I reread your first sentence, and that changes what I was going to write:

”My Fiancé and I are getting married in Tuscany, but will have a few days before the wedding festivities to explore Umbria.”

Two days of an agenda to cover several small towns & two overnight locations while having wedding tasks in your head would be a great way of testing how well you get along in an intense experience! (Said with a smile!). I love staying in these small locations - planning to return to some again next year, and one-night stops are fine for me. But, for two nights before my wedding? Nope.

Suggestion per your request:
Rome to Orvieto. Explore Orvieto and drive over to Assisi to stay both nights in Assisi.
2nd day - have a leisurely morning in Assisi & drive the 40 minutes to Spoleto to explore. Then go over to Spello. Have lunch and walk the very steep lanes for lots of beautiful photos, especially if the flowers are in bloom. Return to Assisi to enjoy what you had to rush through earlier.

Recommendations:
Drive from Rome in the afternoon to Orvieto. Stay two nights in Orvieto.

OR
Drive from Rome to Assisi with a stop in Spoleto. Stay two nights in Assisi. Explore Spello your second day after a leisurely morning in Assisi.

Oh, and if you aren’t familiar with ZTL’s, be sure to read about them before you’re driving in Italy.

Thanks all for the comments. Our latest thought is that we cut out Orvieto and Todi from the plan since they are a bit out of our way. The current plan is to visit Spoleto on the first day, sleep there, drive to Spello in the morning, spend a few hours there, and then continue to Assisi. We will then spend the afternoon and evening in Assisi before departing the next morning.

That sounds like a good plan. Wish you a wonderful wedding day!

Orvieto is easily reached by train from Rome. If it's still in your plans then research if people have found picking up a car in Orvieto convenient.

In past trips to Umbria/Tuscany we've found that two towns a day is easily doable. Leave the hotel by 9am and go to the first, being mindful of ZTL restrictions and conscientiously obeying speed limits since locals know where speed cameras are but you don't. Walk around, explore, take photos. If you like the town then have lunch. If not have lunch at the 2nd place.

I suggest staying in one hotel for the 2 nites. Packing up each nite is a hassle, your next room won't be ready until the afternoon, and we'd prefer not to have all our luggage in the car when we can avoid it. On a related note if your luggage is in the trunk then never open the trunk in a parking lot prior to a visit. Stop a mile or so before arrival and get out anything you might need; no sense showing any potential thieves a car guaranteed to have luggage in it.

For Spello, an American author and her family spent a year living in Spello and she wrote a book (maybe more than one by now) about the experience. See https://michelledamiani.com/