First trip to Italy

If you intend to visit Milan, Which you should its a great and beautiful city, Then you should visit these Historical sites

1. Arch of Peace
2. Terraces of the Cathedral
3. Monumental Cemetery
4. Royal Palace

If you will ask me why you should visit, Then you should read this article, You will be truly amazed to read their history and you might change your plan a bit to take time out for Milan

Instead of Naples, which to me was a horribly dirty city where my wife got pickpocketed, I would suggest you visit the Amalfi Coast after your Rome time. That's 5 nights in the city...so perhaps you may be looking for something less busy.

We did visit Pompeii and it's worth a good 1/2 day visit.

Since Florence and Siena are so close, I would combine those days, staying in one city and day tripping to the other. That will save you a few hours wasted time packing, checking out of one hotel, and checking into another one. I by far prefer Florence, and it's also a transportation hub so it's much easier to do other day trips from Florence than from Siena. Daytrip between the two cities by bus.

Five days in Rome is good – one could easily occupy two or three times that amount of time in Rome. Depending on your interests, additional stops could include the Galleria Borghese, the catacombs, the forum, the pantheon and other wonderful churches, the Colliseum, etc. I would suggest planning an entire day for the Colliseum/Forum/Palatine, and another full day at the Vatican and its museums.

Sounds like a great well paced trip, and eminently do-able by train the whole way.
My only suggestion, especially given your travel time of late September, would be an extra night in the Bay of Naples area instead of Rome.

To Rome (4 nights)
To Sorrento (4 nights) with x3 day excursions to Naples+Pompeii, Capri, Positano+Amalfi.

Definitely go to Naples it is a glorious city. Just be aware.

I agree with JKC. Naples, in all it's grit, chaos, smells and sounds, is an amazing city. Definitely combine three days in the area with Sorrento, Capri, Pompei, etc. Just like any big city like NYC, just be careful with petty criminals at trains stations and tourist sites.

Your plan sounds fine. Firenze and Siena are so different that you might enjoy spending time in each one. You could take a bus to Montalcino from Siena on your second day, if you run out of things to do.

Napoli is beautiful, historic, has some great museums. You will need the same caution there as in any big city.

Is it worth the hassles of a 1-night stay to be in Lucca overnight? If it is, I would not do it on my first night, if I were arriving after a long flight (jetlagged, sleep-deprived). It's just as easy to take the train straight to Florence, then either day trip to Lucca or have your 1-nighter before or after Siena.

Other than that, I'm with Zoe - good itinerary, don't be put off by Naples's bad rap. Be sure to visit the archaeology museum while you're there. It's easy to day-trip to Sorrento and Herculaneum by train as well as Pompeii.

If you can fly out of Naples, that's perfect. But it's easy enough to go to the Rome airport, changing trains at Rome's Termini station.

Since so many people are praising Naples, I'm going to sound a dissenting cry. You need to think about your tolerance for large, crowded, chaotic, dirty cities. Only you know that. I grew up in Chicago, lived in London for a year, have visited NYC, Paris, Rome, Athens, Berlin, etc. I live in the SF Bay Area, so I am not unaccustomed to homeless people and beggars on the streets. However, I must say that Naples is the only place in Europe that I couldn't wait to leave. In my opinion, the Nat'l Archaeological Museum is the only reason to go there.

mal,

Your itinerary looks reasonably well organized, but IMO a few minor changes would be beneficial. A few thoughts.....

• As some of the others mentioned, I wouldn't bother with one night in Lucca as you won't really be able to see much. You'll basically have one evening in a jet-lagged state and you'll have to be out of your hotel at about 10:00 the next morning. I'd suggest going directly to Florence and adding a night there. A day trip to Lucca is very easy.
• I'd suggest keeping your two nights in Siena as that will provide a nice glimpse of the city in the evenings. Travel from Florence to Siena is easier by Bus, as you'll be dropped in the centre of town rather than at the bottom of the hill where the rail station is located.
• Five nights in Rome is good, but plan your touring carefully as there's lots to see.
• For your stay in the south, Naples is certainly a possibility but you could also consider staying in Sorrento with a day trip to Naples and Pompeii. FWIW, I like Naples and don't have a problem with the "gritty" nature of the city. However, one "caveat" to mention - Naples / Pompeii / Sorrento travel will be via Circumvesuviana (train) which is also a bit "gritty" and can be intimidating to some.

If you haven't already got one one, I'd suggest packing along a copy of the Italy guidebook as that will be an excellent resource to have at hand during your trip. Also, there are a few "caveats" to be aware of when using any public transit in Italy. If you're not aware of those and need further information, post another note.

Just throwing out some thoughts: Venice is only 2 hours from Florence by train. If you haven't been to Italy before, I would put it near the top of the list. We love Siena, and it's a fun place to walk around in the evening. We travel solely by train (or bus) in Italy, too.

Venice (2-3 nights) nice to have an extra day to get over the jetlag
Verona (2 nights) another option that is a nice town for tourists
Florence ( 3 nights)
Siena ( 2 nights)
Orvieto (2 nights)
Rome ( 5 nights) - fly home from Rome. (Check out Ostia Antica as an alternate to Pompeii which is on the edge of Rome - easy transportation)