Ascoli Piceno to Siena
 

Hi Melo,
in my opinion Castellucio rates as one of Travel's Great Moments IF one is there for sunrise and is lucky to catch one of that mountain valley's famed 'thermal inversions'. The entire massive valley fills with milky white fog at such times. Since the earthquake, the hilltop village itself cannot be entered due to safety concerns (ruptured gas lines) but folks apparently are still being allowed to drive up the periphery of the village, where the vendors set up stands to sell stuff. Our advice would be to drive as far up the adjoined mountain trail as possible for the best views.
Norcia fared better in its recovery (ironic given that it sits directly atop the fault line) and would make a great lunch stop.

We don't have experience in the other locations you list, so will defer to others regarding those possibilities.
*Be sure to buy some panforte in Siena--they invented it.
Tante belle cose
I am done. the drive

Thank you very much Zebec. Did you have an experience to drive between Castelluccio and Norcia?

Its been several years since we drove that area (and hopefully restorations have progressed since the earthquake), but its unmissable. You might want to scroll post from post#17 onwards of my thread https://www.fodors.com/community/europe/visiting-le-marche-and-umbria-1648112/#post16733092 with some (albeit dated) input around the Catellucio - Norcia road/the gorgeous Piano Grande with some photos.

As for Trasimeno, we've spent a few nights in Cortona (very charming but further away) before. Castiglione del Lago (on the lakeshore) is a gem.

Hi Meloman2,
To add to zebec's excellent advice, Castellucio is highly recommended as a route. We were there both last summer and the summer before, when the wild flowers bloom in the plain in June. I think they won't quite be out by late April, but there will certainly be things to see. Don't forget to spot the forest shaped like Italy as you descend from Forca di Presta (see below).
It is also worth leaving some time to walk the accessible path at Forca di Presta which you will most likely drive past en route; it's a great way to get some air and there is usually sufficient roadside parking (Castellucio's can be somewhat chaotic).
When you leave Castellucio take care when descending on the road to Visso - it has many hairpin bends. Like Castellucio, Visso also suffered from the 2016-17 earthquakes, but is slowly returning to life.

Yes Melo,
We had a *driver and went from Norcia to Castellucio. True story: as we arrived in the latter who should gallop on horseback right by our vehicle but Tom Cruise's ex, the actress Katie Holmes. She was not alone. We did not recognize her then but nearby folks were quick to ask us whether we'd realized whom that rider had been! Our landlords up there were Giuseppe Caponecchi and his mom Gianna. Years later after the quake, we got an email from Giuseppe's adult daughter who was finishing her doctorate by creating a report for the local authorities on how best to support local tourism. We were then asked to fill out a questionnaire.

*notes from our Umbrian trip journal:
-'first stop outa Norcia=Santa Scolastica vista lookout
-secondo stop=Pizzo del Diablo Mt. rock wall then Mt Ventosola
-F. di Da S. Croce pass
-there was an obvious pull-off place to park once arriving at piano Grande, where one can admire the Mt Sibillini park and Mt Vettore

I'm looking at the Michelin map and PJD's hairpins en route to Visso would include Forca di Gualdo, Gualdo itself, Mad. di Cona chapel then Castelsantangela sur Nera.
It is a lovely area and some prefer it to Tuscany.

I am done. the lucky travelers