I have already gotten so much helpful advice from this forum! Thanks to all! I would like to hear opinions on where we should go on our trip in late Oct. - early Nov. I have never been to Italy, and will be with my newly minted lawyer son who traveled there extensively as a student. We arrive in Rome on Oct. 26 - and fly home from Venice (one of the few places he hasn't been) 16 nights later. (I did that routing based on recommendations from the Forum). I love ancient things, archeaology, all things from ancient Rome and Greece. I am more interested in the medieval than the baroque, and quaint rural areas and beautiful scenery is more important than museums full of old masters. I know we can't do it all - and am willing to assume I will go back some day. I would rather not be too hurried and the idea of staying in a place for several nights - and making trips from there - is appealing. I am also aware that the days will be shorter, and the weather changeable that time of year. Given all that - I have begun with the following:
Rome (we will be joined by friends while in the city) - 3 or 4 nights
Pompeii/Sorrento/Amalfi Coast (or just Pompeii ?) - 2 to 4nights
Tuscany/Florence/Siena(with a car) 4-5 nights
Venice - 3-4 nights
Is that too much? Should I shorten the days somewhere and add them somewhere else? It is hard for me to not put Assissi, Umbria and Capri on the list as well. Should we just go down to Pompeii for a day (that is a MUST SEE for me) and then spend the remainder of the days between Rome and Venice in the Tuscany area? I read in one post that it will be harvest or pressing time for olives. That would be fun. Your thoughts?

You do have time for 4 destinations and still do them well. I like your choices, but when I read the title I was going to suggest south--AC ad Sicily. That time of year you can expect rain and short days. I think I would start north and end south.

I think most of these decisions/choices are yours to make and depend on how much moving around you want to do. Personally, I think a day trip to the Pompeii excavations without seeing the Naples archeology museum is only half the story. And being in the neighborhood but not seeing Capri and the Amalfi Coast would drive me crazy. Could you fly into Naples rather than Rome? Or fly into Venice at the beginning and fly home from Naples at the end?

With only 16 days and wanting to see Rome and Venice and the Naples area, you have to choose between Tuscany/Florence and Umbria/Assisi. Your call.

We are starting in Rome in order to join friends there for a few days. And we found a great connection out of Venice, that doesn't leave until 10am - thus making the trip to the airport a bit easier ( I hope ). So our plane reservations are set. We could opt for going south from Rome - however, and spend 7-8 days in the Amalfi Coast/Sicly area - saving Tuscany for another trip. My son would love to see Sicily which would be new for him, and I would indeed like to see the museum in Naples. Would that be enough time to do Pompeii/Naples, the AC, Capri and Sicily? Could we fly or take the train from there to Venice - where we would spend the final days before flying home?

Not really !
You set your parameters when you set your flights. Sicily would take a week or more. Do it next time.

For ancient Greek and Roman, I would do Rome/south. Naples area and Sicily. I would leave Rome/north for next time.

Like others, I would suggest south (Sicily) at that time of year. Snav has overnight ferries from Naples to Palermo. You could also use one of the budget airlines between Rome/Naples-Sicily - Venice.

How about-

Rome
Naples for 2 nights, visiting Pompeii/Naples
Southern Tuscany or Umbria (Pick one. Also, you could stay in S Tuscany and drive over to Assisi one day)
Venice

The food in Tuscany/Umbria is terrific in Oct/Nov.

Stay in the Val d'Orcia area of Tuscany.

Given your description of your interests, I recommend Sicily while in the area of the Amalfi, be sure to include Salerno and Paestum

You seem to have selected Venezia on the basis of forum recommendations rather than your own interests. . But I suggest you re-think this trip and focus on your own interests, and eliminate Venezia and Firenze (Florence). I recommend Orvieto, but no further north than Siena. Otherwise, stick to the south, especially for that time of year.

I would begin in Siena and do Sicily last.

Yes you need to stretch out what you ain to do in the Naples area (though Sicily at the same time looks a bit much) then aim to do enough in Tuscany/ Umbria. So if it were my time I would swing an extra aday into T/U and drop time from Napoli

Thanks to all. We picked Venice because my son has never been there and it was tops on his list. If after Rome, we did 2-3 nights in the Naples area and then headed to the southern Tuscany/Umbria area - should we do it by car? Would we then drive the car all the way to Venice?

Hi nancythenice:

With Pompei as a "must see" let me suggest Positano as your accommodation on the Amalfi Coast. You would be in a location of unparalleled beauty and at the same time near to The Stabian Villas, Pompei, Herculaneum and the Flegria Fields in
one direction and Paestum, Velia , Amalfi and Ravello in the other. Four to five days would allow you to enjoy beauty, history and personal inspiration. I www.walkingwiththegods.com owned by an American who has remarkably reasonable rates and creates personal itineraries based on his intimate knowledge of the area.

One of the problems with this late a trip is whether hotels and restaurants etc are open in the South. Positano for instance, tends to "close" after mid October. Do some careful research on your hotels and chosen resort area, to make sure it's worth seeing at that time of the year.

Personally, I feel that the winter doesn't do justice to the Amalfi coast, even allowing for lack of crowds, or maybe because of it. The weather obviously plays a big part in what is essentially an outdoor experience.

Good post Lifeman. Certain places in the south do close down for that season. Also transportation schedules are cut back. I also agree that places such as Amalfi coast lose a lot in "winter". Research and book carefully.

You can pick up the car in/near Naples and drive to Tuscany or train to Chuisi or Orvieto and pick up your car there. You can train from Chuisi to Venice or drive, depending on how comfortable you are with driving. I once took the train from Chuisi to Venice and it took a long tme, requiring a change either in Florence or Bologna. Also, check the train schedules- it may be faster to drop the car in Arezzo and train to Venice fom there.

Some cautions:

Postiano is not a good base for seeing Pompeii, but it is far better to see Pompeii in October or November, so if that is priority, do it, despite the fact that you won't have a summrertime experience in the resort areas. Don't book a hotel where you pay for the terrace view.

Most places along the Amalfi coast will be open, no problem. And certainly any hotel you've already booked is not going to close on you!

Chiusi has more than one car-rental office, not all near the train station, so if you are carrying luggage, you might want to think about that.

Again, you should do more research on what Tuscan or Umbrian towns would interest you. Given your descriptions of your interests, I would think you'd love Perugia and Siena, and Orvieto. The wine towns of the val d'Orcia might interest you less. You decide.

You are all giving me lots of ideas. And yes - I need to do more research on Tuscan/Umbrian towns. With regard to the A/C I have some concerns that what is essentially a summer resort area might be kind of sad in November. Deserted ruins are wonderful - but deserted coastal resorts not so much. Would Sicily be that way in winter? I hadn't considered Sicily, but it looks like we could spend several days there and then fly straight to Venice - leaving Tuscany/Florence for another trip - and there is certainly a lot of history there to explore. Alternatively, I am thinking we could do Pompeii/Naples museum/Hurculaneum for two days, then on a third day take the bus down the coast road and go to Paestum - focusing more on the ancient history than anything else - before moving on. From reading other posts, it sounds like Sorrento is often used as a base for that type of exploration - and that it is preferable to stay there rather than in Naples. Could we leave Rome late in the afternoon/evening and go to Sorrento for the night - beginning our explorations using the local trains the next day? Or would it be better to spend the night in Rome, and move the next morning - using part of that day for sightseeing? If we did that, I would like to stop in Naples and do the museum. Could we leave our bags at the train station? Or should we get a hotel in Naples, and do our day trips from there?

There is a train line that runs between Napoli and Salerno, probably the easiest way to see Paestum.

Napoli -- ancient Neapolis -- is a chaotic place that some of us love and others hate. Sorrento is a much more picturesque place, and calmer. In October or November all of Italy has unpredictable weather, cool and possibly rainy -- but it is not winter. Even if it was, in Napoli, December (and much of late November) has a lot of interesting and unique Christmas preparations.

I don't know if you will find resorts sad in Italy. A lot of people are really happy the crowds have gone! But you can't swim, and some hotels and restaurants use the time to do repairs and renovations. But certainly not the monuments. And apart from Taormina, not much of Sicily is just a tourist coastal resort. Most of Sicily is still dominated by the Sicilians doing what they do all year round, even near the tourist attractions. (That is not true of the Amalfi and the most coastal parts of Sorrento, but it is true of Napoli, Salerno and Pompeii.)

It is always a really tough call advising people about choosing some Italian destinations over others. Most people recommend and enjoy the most picturesque parts of Italy, irrespective of their history. But if you have a very strong preference for Greek and medieval, as opposed to Renaissance, baroque (or Etruscan) then you personally might find it most rewarding to see the Greek underpinnings of Italy in the areas between Napoli and Salerno and onto Sicily (and the Byzantium in Venezia) and catch up with the Renaissance later.

But you will hardly be disappointed in Toscana if you decide to go there. Just be aware that you might encounter rain -- and even dustings of snow in late November -- as the days progress in late autumn.

Zeppole - thanks so much for the thoughtful information. I have traveled previously in the late fall and early spring - and never minded the cold, or even the snow - but have usually been in cities where, although it gets dark early,there are things to do in the evening. I will think about Salerno as an alternative to Sorrento. I have begun reading about Sicily. It sounds wonderful - but I wonder if it doesn't deserve more than just 3-4 days.

I go to Sicily every year. I'm still finding new and wonderful things to see and do, and I still spend time re-enjoying all the wonderful old things there are to see and do. The more you learn about Sicily, the more it will call to you. The more you go, the more you will want to return.