I will be arriving in Rome after a transatlantic cruise. I've already done most of Rome on previous trips. I would like a suggestion to extend my vacation for another 3-5 days and end up in a city where I can board a flight back to the U.S. Any ideas?
The is always Florence, Milan. You should be able to catch a direct flight back to the US from Milan. From Florence, it would be a connecting flight somewhere in Europe and then the US. A vague question.
Have you visited Palermo? That could be a good 3 days, with side-trips. I loved walking around in Palermo.
I vote for Milan. With side trips to Venice, Verona and Varenna.
Milan makes the most sense. It will give you the most choices for return flights to the US. From Milan, you could easily visit the Lake Como area, e.g. Bellagio. On the way from Rome to Milan you could easily visit Florence.
I'm guessing you're on a repositioning cruise, so it will be early in the season. Anywhere in Italy should be lovely. I vote 2 days in Florence and 3 in Venice.
I recommend Sorrento / Amalfi Coast (my favorite place in Italy) and fly back from Naples. It's an easy train ride from Rome.
Another vote for the Amalfi Coast, Sorrento, Amalfi, Ravello, Positano. Such great memories.