Some flexible time in Italy after Rome, before Milan

For your Naples day tripping, you may want to consider Pompeii also. If you start early from Rome (70 min. Rome to Naples by train), you could probably squeeze Pompeii for a 3 hr. visit to the ruins. Naples is a beautiful city of course, and there will be plenty to keep you busy for that day. Capri, Sorrent and the Amalfi coast are probably not at their top that time of the year, but that will depend on the weather of course. In any case I wouldn't suggest swimming in the sea in March, you'll freeze. For the 5 days between Rome and Milan, since you are traveling by train, you may want to consider small town options that are easily reached by train more or less along the Rome-Milan line. Some ideas along the main line (excl. Florence, which you have seen): Orvieto, Cortona, Arezzo, Bologna, Parma. Assisi and Perugia are also reachable by train and good options, however you'll have to go a little off course (East of the main path). Gubbio is nice but you'll need to add well over one hour by bus from Perugia. Also you want to make sure you have enough time for Milan. It may not be Rome or Florence, but Milan has enough to keep you busy for at least one full day.

Thanks everyone! Lots of great ideas so far. I'm a little surprised looking at the Rail Europe site I don't see any trains from Naples to Rome later than one or two in the afternoon. That can't be correct, can it? This will be the second week in March before I reach Tuscany/Umbria, so I think things may be beginning to wake up slightly by then. May be able to pick a central location and then visit both Orvieto and Assisi. (and I haven't forgotten about Gubbio thanks!) RJ

you have to visit Gubbio, in Umbria, a real pearl.

Logistically, it would be simpler for you to do a night or two in Naples between your time in Sicily and Rome. (You'll be passing through it anyway.) Is that an option for you?

Michael thanks! I considered that actually but got a really good hotel rate in Rome and a good deal from Sicily to Rome so, I will try to do Naples as a day trip.

Ross, I would definitely recommend a visit to Orvieto. It's a beautiful Umbrian hill town with an interesting history. It likely won't be too lively in February, which may be a good thing. If your budget allows, you might consider a dinner at Ristorante L'Antica Rupe. I found the food there to be excellent! A few of the sights that I enjoyed there were St. Patrick's Well, the Underground tour and of course the Duomo with the incredible Signorelli Frescoes. You could also take a day trip to the somewhat unique Civita di Bagnoregio, although again I'm not sure what that will be like at that time of year. Cheers!

Ross, Just curious, why are you looking at the Rail Europe website???? I checked the Trenitalia website and there are numerous trains from Napoli Centrale to Roma Termini, about every half hour throughout the day. You can also check using the bahn.de (German Rail) website. Current fares are currently as low as €11.20 (but of course that will be a slower train). Cheers!

Hey Ken, Oh, RailEurope was a site recommended by Rick's bunch. I used it to book my night train from Palermo to Rome. They apparently don't have all the times maybe just seeing the ones they can sell this far in advance. Anyway, for the rest of my travel, I'll book when I get to Italy. I can't imagine it can be too hard to get from Rome to Milan in March! Happy Holidays buddy!

A couple of other hill towns to consider: Todi, Spello (about 7 km from Assisi), Cortona.

Ross: For very good instructions on train travel in Italy, see RonInRome.com. He even has pictures showing how to purchase your ticket out of a vending machine in the train stations. You've received very good guidance above. Roberto and Ken really know what they're talking about. There are so many incredible hill country cities to visit. One option would be to visit Orvieto, and pick a rental car at Hertzacross from the train station. Tuscany is best seen behind the wheel of a car. I especially love the area south of Florence, including San Gim. and Volterra.
Turn the car in at Florence or on another city along the train route.