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Rick now has a guidebook for Sicily, which would definitely be worthwhile for you. Although I don't always agree with the places he identifies as top sights, my tastes are odd; I think he does a really good job of highlighting the key places of general interest.

It sounds as if you're planning to spend just a bit over a week in Sicily. It is a very large island; you'll have to be extremely selective with such a short visit. Given that Sicily is a bit awkward to reach (it's a very long train ride from Rome, so I'd fly), I'd suggest spending all your non-Rome time in Sicily.

What type of sights and experiences are you interested in--churches? classical ruins? other historic sites? food? natural beauty?

I'm tempted to suggest you fly into Catania (the largest airport on the island) and spend your initial two Sicily days down around Siracusa. That area is a great favorite of almost everyone, with the lovely Ortygia district and a number of atmospheric Baroque towns in the surrounding area. However, two days would only scratch the service there--enough for Ortygia and Siracusa, but probably not for side trips.

I am not a fan of Taormina, which is extremely touristy and has high hotel rates, but it is undeniably beautiful, and some people like it a lot. It would be suitable for a two-night stay; I think Etna side trips are possible, and I believe previous posters have mentioned other side trips they've enjoyed while staying in Taormina.

While you're staying in Palermo, you can easily take day trips to Cefalu and Monreale. The Villa Romana del Casale might also be possible, although it will take more time to reach.

There are many other points of interest in Sicily, and quite a lot of sights in Palermo, but we need more info on how much time you'll have available and your interests.

Hello Acraven -
Thanks for your insights already.

What I know is that I fly into Rome on 10/24 - early afternoon. My son will join me either Friday night or Saturday morning. We want to see the Colosseum and probably a food tasting tour. We've both been to Rome before, know it will be crowded, so only have a couple of days. We were thinking of leaving on Monday. He has to be back in Palermo by Wednesday night. Can we see Naples for a day or 2? What would be best way to get there. Maybe we don't have enough time.....

Once in Sicily, our home base will be Palermo. You are right, I only have about 1 week to explore. He will be there much longer. We like art, nature, cultural history, ancient sites, and food. Churches are not highest priority but we enjoy when we come across.

We were planning to fly to Palermo from Rome, but maybe we take train to Naples instead?

There are frequent, fast trains from Rome to Naples, so you can visit Naples easily if you want to spend a day or two that way. Naples has lots of worthwhile sights and is also a convenient base for seeing Herculaneum, Pompeii, the islands in the Gulf of Naples, etc. With only a day or two, you'd need to pick just a very few sightseeing targets. The only thing I know of in Naples that requires prebooking is the Capella Sansevero, which houses the Veiled Christ sculpture. It sells out well in advance. I think you'd have to be unlucky to run into a significant delay buying tickets at the Archaeological Museum, Herculaneum of Pompeii. I trust someone will correct me if they've run into such difficulties.

EasyJet and RyanAir both fly between Naples and the two largest cities in Sicily--Palermo and Catania. You can check schedules on skyscanner.com. I don't know whether flights operate daily. I haven't flown into or out of Naples, but I'd certainly explore using it as the departure point rather than returning to Rome to fly to Sicily.

Colosseum tickets can be tricky. I'd check on availability right away.

Some quick locations from Rome - about an hour by train, that are good for two days are either Caserta or Tivoli.

When I went to Palermo, I just flew EasyJet from Rome…or maybe it was another inexpensive carrier.

Thank you all for your ideas and input. Helpful!

5 days for Rome is perfect, you have time to visit everything and the weather will still be ok. Now from Rome to reach Palermo, you can either take the train to Naples and then the boat to Palermo (that's what we've done), or yeah take the plane. But I have to say the train journey is quite pleasant and then the boat takes 8h (bight boat).
Then when you're in Palermo, you can visit the city (UNESCO World Heritage Site) and go around the markets and the theatres. If you don't have a car, I would suggest you stayed in the city and maybe do one-day trips to the Aeolian islands (we did Filicudi, Vulcano and Lipari, check on ferry hopper though bc I am not sure if the ferries run in October). In general I would say go for local food, the markets and the buildings of the city in general. Enjoy!