I'm in the planning stage for a trip in early October 2020. Here's what I have in mind:
Fly in to MXP, bus to Stresa – 3 nights
Train or bus to Bergamo (Citta Antica) – 3 nights
Train to Bologna – 4 nights
Bus to Siena – 5 nights
Bus, possibly drive, to Perugia – 3 nights
Train to Orvieto – 2 nights
Train to Ostia Antica – 1 night
Fly out of FCO
We've been to Siena and Bologna before and have toured Umbria by car. It seems that getting a car in Siena and dropping it off in Orvieto may make sense but we would prefer to stick with public transport.
Does this sequence make sense or would we be better off reversing the order (if so, we would head directly to Orvieto and go to Milan for the last night)? One concern I have is that we may end up in Perugia during Eurochocolate. While I love chocolate I'm concerned that the town may be too crowded to enjoy.
If you have recommendations on where to stay in any of these locations I appreciate your input.