Tuscany & Umbria hidden gems

Hi Kim,
Rather than parsing through and editing, I've simply pasted an old Umbria post of ours below. Hopefully some of it may inform your efforts - tante belle cose!
I am done. the end.

'But we do have some experience in Umbria (got a great rental to recco in Bevagna, overlooking square). As train riders there, you will be using Foligno station as a hub, I'll reckon.

Places to eat could possibly include:
Spoleto: family-run Taverna La Lanterna was an unpretentious place that served VG food & drink at a reasonable price point. Afterwards, maybe check out the 2 nearby side-by-side food shops: Salumeria Padrichelli & Forno Panficio Santini. Whether you are into bars or not, Tric Trac by the duomo is hard to resist, largely due to its amazing location.
Trevi: the splurge Antica Dimora alla Rocca has a smallish wonderful patio out front. We had drinks there midday and it was perfect. Very sympa, quiet, not crowded. If you decide to carry on to the Fonti di Clitunno, note that the site has its own on-site restaurant, a decent one.
IMHO, L'Alchemista in Montefalco is at its best for Sat. morn brunch. The bacon/eggs dish that they serve then is worth the cost of one’s flight and besides, the weekly flower market will give you added visual value.
Spello has a must must must-do lunch spot called Enoteca Properzio. The food and wine were world-class, perhaps the best Pinot that we've ever tasted. *Our mentioning this wine bar/cafe once drew some criticism over on the Lonely Planet Thorn Tree forum, with a couple smug European respondents putting it down because its wine list 'seemed to cater to Americans' (their words). Despite not being from the USA, I countered that American men had once crossed an ocean to play a major role in freeing Europe from the Nazis: "If I were European, I'd show just a little respect."

Lesser-known lodgings/best-kept secret: S. Pietro en Valle is an actual historic monastery in a fantastic setting. Outstanding breakfasts and great hiking nearby--we met a Denver couple who'd come there for their 7th straight year. Website does not do it justice.

Wrecked by the earthquake but still worth the drive to its mountainous park location near the Le Marche border: our beloved Castelluccio. *Sometimes if one gets lucky, there occurs one of the park's incredible 'thermal inversions'. The entire plain fills with a milky white fog, a peak experience in the truest sense of the word.

Finally one of our all-time faves, Bevagna. Plenty of eateries, but the one that we visited the most was tiny, perfect Bottega di Assu. Excellent salads, unpretentious, very small so prime outdoor tables get grabbed quickly. The zany owner Maria's adult daughter runs the more upscale Spirito Divino around the corner. I still dream of Assu. Sigh...

Special Note: some judgmental poster over on Trip Advisor once said some harsh things about Bevagna's Osteria Antiche Sere. Owner Luciano was so offended that he soon hung the following note by his door:

'SEGUACI DI TRIP ADVISOR? PSEUDOGASTRONOMI? INCONTENTABILITI? (my fave part) PERCUSSIONISTI SCROTALI ! NON E IL POSTO VER VOL. PIU AVANTI CI SONO ALTRI RISTORANTE!'

(translation)
'Gosh how I wish that you had come to me personally after you found an extra anchovy on your dish. And how could anyone argue that Matia Bazaar was better than PFM? They were both excellent.'

Really little in Tuscany: Pontremoli
Four times Pontremoli's population but still with a small historic center in Umbria: Gubbio

We stayed and ate at a “resort” in Torgiano called Le Tre Vasalle. Really good restaurant. Spa, pool, parking and easy access to everywhere if you have a car. We really liked this place, if you’re looking for a spa experience. Torgiano is just a town, however.

Assisi is a must see in Umbria.
Perugia is worth at least a day.
Gubbio for half a day.
Orvieto if you have time.
Spoleto is great.

We quite enjoy Spello and there is a wonderful hike from Spello to Collepina and back in a loop, which I wrote about here https://projecteasyhiker.com/2017/10/06/spello-to-collepino-along-a-roman-aqueduct/.

Spello itself is on a hill with the train station at the bottom. We found accepting locals, good restaurants, quiet evenings. We stayed a week and enjoyed all of our daytrips by train, but a car would make it easier. Spoleto, Assisi, Perugia, and more as mentioned above.