I am planning to start in Assisi next May moving to Venice, Verona, and Lake Como. We have previously been to Rome, Florence, and Sienna. I plan to depart out of Milan but am still figuring out the best arrival airport. I can fly direct to and from Milan reasonably (from Miami) but a multi city itinerary flying into Rome and out of Milan requires two flights and several of these that are reasonably priced (American, Tap Portugal) have tight connections. (like just over an hour in Lisbon and Madrid) So I have been going back and forth on wisdom of flying to Milan directly and taking the train to Assisi versus flying to Rome with a connection and taking train to Assisi.
There is a train to Assisi from Milan that takes 4.5 hours every two hours with one connection. This routing has a 13 minute connection in Florence. Is this doable? I think the train from Florence to Assisi is a regional train so if we missed it, we could take a later train. But of course, that means it will take longer to get to Assisi.
I have flown into Milan three times previously and it was very efficient except for luggage. I don't plan to check luggage this time. I was thinking 3 hours from arrival time to get though airport to Milan station to get a train. Does that seem reasonable? I know the advice is to not prepurchase train tickets for day of arrival but I am trying to figure out likely scenarios, since the routing of 4.5 hours is only available every 2 hours.
Trip from Rome airport to Assisi is short of 3 hours with one connection. Like from Milan, there are longer routes with more connections which I of course do not prefer.
Time wise, I don't think there is much difference between flying directly to Milan, taking train to Milan Centrale, and then train to Assisi via Florence and taking flight to Rome with a connection and then taking train to Assisi via Rome Tirbutina. Money wise it is cheaper to fly round trip into Milan and take the train but the difference is not huge by the time you consider that the train to Assisi is more expensive than that from Rome.
Thoughts?