I'm having analysis-paralysis and hoping the travel community can help. I will be traveling with my 70-ish year old mother this October. We have yet to book flights; but flying into most major cities and out of another are similar in cost, so we have options.
What we know for sure:
Bologna for 4 full days (not including travel days)
We are flying into one city and out of another after confirming itinerary (if multi city makes sense in the end)
We've both been to Italy prior (2019 and I've been 2 other times). During our 2019 trip we did Rome-Florence-Venice.
We want 3 bases total for the trip (Bologna being one of them)
Tentative dates Oct 9-25 (those include the travel days)
While I've driven in Italy on a previous trip; I'd prefer not to do that unless I'm convinced since it would just be me driving and not my mother
We enjoy art, architecture, history, cooking, wine, wandering cities. My mother would not be able to do strenuous hikes/bike riding/swimming (doesn't know how). She has no mobility issues otherwise.
Where I'm stuck:
Puglia and Umbria have both been brought up as places my mother would like to visit. I'm trying to decide between the two. We will fly/train between cities. I am not sure how we could do them both due to getting between them.
Should we start in Rome or is there another city we should consider
My father has MS and we are thinking this might be our last Europe trip together as it will be more difficult for her to steal 2+ weeks away in the future, so I'm wanting to plan something special for her. Thank you for helping and let me know if there are questions I can answer. Appreciate you all.