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October 2020 Travel Recommendations

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.

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