Sequence of Cities?

Whether or not this is “the best,” here’s what we did in 2012:

1) Rome for 1 week. You could pop up and back to Florence from Rome, although we saved Florence for subsequent trips to Italy

2) We then flew to Palermo, and had a rental car for the next week to tour Sicily

3) Ferry back to the mainland with the car, drove north to Sorrento, visiting Positano en route

4) Turned in rental car before taking train back to Rome for our flight home the next day. Saw Ostia Antica that last afternoon, a 3 minute walk after getting off the train.

It doesn’t really matter since you plan to fly into Rome and return from Rome. The other locations are in different directions from Rome, with Rome being the hub.

To go to Palermo you will likely need to fly from Rome.

Florence is an easy 1.5 hour train ride from Rome.

Positano from Rome requires 3 legs:
High speed train to Naples (70 min)+commuter train to Sorrento (70min)+bus to Positano (45 min).

Potentially you could start in Florence first on the day of arrival. From the Rome airport you can take a train to Florence (in most cases with a change at Rome central Termini train station) and be in Florence a little over 2 hours later. From Florence (or nearby Pisa) you could also fly to Palermo if those flights resume after Covid.

From Palermo you might be able to fly directly to Naples (which is near Positano) without passing through Rome.. However that all depends on the travel situation when you go. Many flights that existed before the pandemic now no longer exist, therefore only flights from/to Rome (Italy’s largest airport) are certain to be in place.

Upon arrival go to Positano- then Palermo ( fly from Naples)- then to Florence (via air) and end in Rome.

My $0.02

When in the fall? Palermo is likely to be much warmer than Florence.

Another option from Palermo to Positano is the overnight train from Palermo to Salerno and then a bus or ferry to Positano. Or take the overnight train to Naples and continue as mentioned above.

Best to END your trip where you leave. This always works best for me, you use your jet lag first day in transit, don’t have a wasted day when you return to a city for one day just for the airport, and lets you focus.

Therefore, if you fly into Rome, immediately leave it by train or flight to another place. Do your actual visit to Rome last.

Two ideas - arrive Rome, fly to Palermo because it’s the most distant then work your way back. Next Positano (because you can fly Palermo to Naples), then train to Florence, then train to Rome.

Or - arrive Rome, train to Florence. Then down to Positano by train, then fly from Naples to Palermo. Then fly back to Rome.

I had a similar Italy schedule planned last year. I like Mira's suggestion. Our plan was to fly from Rome to Sicily then work our way back north. There were open-jaw options to fly from the U.S. into Sicily and then out of Rome....but, the U.S-Rome and Rome-Palermo flights were super cheap then, not sure if they will be as inexpensive in the future.

I urge you not to take the overnight train. I took it from Rome to Catania in 2015. It was the most miserable night of my life--worse than the overnight flight to Europe even though I was lying down. The tracks must be in bad shape, because the train carriage jerked from side to side constantly, and I got not one minute of sleep. It messed up my body clock for more than 24 hours, and I lost an entire day of sightseeing.

I get that most want to fly nonstop to Rome, but depending on where you are flying from, it is worthwhile to at least check into flights to CAT or PMO involving only one stop.
What month? I would want a good chance of nice weather for Positano.

How long is your planned trip?

The more I learn about Italy the longer my trip becomes! No surprise there. As I’m planning right now I’d like to go for two months. In October I have a 21 day reservation in Rome; otherwise I’m lucky because I’m free as a bird!
thank you for the warning about the night train. It’s easy to see from your description that it’s not for me.

Two months would be glorious! Our trip, described above, was for 3 weeks, and you’ll have that whole time in Rome alone. This was a trip at the end of December/early January. The one week on Sicily was the week of Christmas, and we did a counter-clockwise circuit of the island over that week. More time would do Palermo and Sicily more justice.

November is a great time in Florence. I made trips there 3 years in a row in November, 2017 thru 2019. It could rain a bit some of the time, but crowds were down and sights were open. What a great dining destination, too!

I ALWAYS end a trip where I need to leave for home from. The suggestion to start south and work back up is a good one.

Keep temperatures in mind. We have been to Sicily twice in mid October and it still was warm, not hot, but definitely warm.

Thank you everyone. All of this is food for thought. Fingers crossed for travel sometime in 2021!