Trip to Sicily

Truly, one week in Sicily is not enough time. It is quite a large island with important sights scattered all over. In my view, 2 weeks is a near minimum there, and closer to 3 weeks is better.

I think one week in Greece is also inadequate; as an island nation, it requires a good bit of time to move from one place to the next. So I'd just add your potential Sicily time to the Greek part of your trip. Edited to add: I should clarify that I wasn't thinking about a cruise of the Greek islands, but a do-it-yourself trip. I think seeing a string of Greek port towns isn't an ideal way to see Greece. For someone who truly has only one week, perhaps it's not a bad way to go. It would frustrate me greatly.

You have lots of time before your trip. Your questions suggest to me that you haven't done much research yet. Visit your local library and pick up at least one good guidebook to Greece and one to Italy. Do some reading. See what appeals to you. I know what would happen if I did that: I'd find so much to do in each country that I'd plan a single-country trip, but plenty of people would opt to do the split.

Sicily- need two weeks at least.
Greece/ No to a cruise. Stay on land and really experience Greece, not a brief crowded photo op. Ferries connect islands as well as some flights. Athens deserves time too.

Ditto what acraven said. I was recently there for a little over 2 weeks and could have easily found places to visit for another week.

Thanks everyone, you have given me lots to think about... and it's true, I haven't done a whole lot of research, especially in Greece, but did a lot of research for last years trip, it was truly exhausting and time consuming, but I'm on it, thank you.

In this case, you really do need to do a good bit of research before committing to your flights. Greece is rather isolated, requiring a flight or long ferry trip in. And of course moving around within the country is a rather slow process. It would be a real shame to buy airline tickets into Athens and out of Venice (just as one example), only to decide later that you would prefer to devote the entire trip to Greece or Italy. We have had posters who did that--picking flight gateways that were very far apart and thinking they'd just pop into a few places between them without investigating the logistics beforehand. It can be a costly error in terms of money or time, or both.

As acraven has indicated, it may look easy on a map, but when you're on the ground you use up lots of time going from place to place, whether it's on a single island, a group of islands, or up a long stretch of coast.

What are your interests? Do you want to explore quaint villages? Ancient Roman and Greek ruins? Loll on the beach (sandy or pebbly)? Hike?

I did a cruise to the Greek islands and enjoyed seeing the islands this way. Of course you only have a cursory exposure but they are still quite nice. The sea and islands are a beautiful view from on board a ship.

Sicily can easily take more than a week to see but you can certainly see some to the sites in a week. Taormina would be a nice place to spend a few days, a charming town with views of the sea and close to Mount Etna. I found the Sicilian people to be friendly to Americans, although there are not as many Sicilians who speak English as perhaps in more tourist traveled areas (no problem in places like Taormina).

For a September trip I would start with the Northern areas you plan to visit and travel South as you go along because it can be hot and humid in September. If it were me I would consider October because it is cooler but then you risk rain in the later part of the month.

True in that it rained quite a bit in mid-October a few years ago when we visited Taormina. And it was so foggy for the most part we couldn't even see Mt .Etna until we were flying out of Catania.

Next year--hopefully--we will be coming down from Naples by train through Calabria and taking the train-ferry across the Strait of Messina, something I've always wanted to do. We will revisit Taormina to meet up with some acquaintances from our previous trip, then are basing a few nights in Cefalu before flying out of Palermo. Planning on using the Cefalu-based Angelo Maggio (Massimo Villas) as a guide, and to make the most of our short time there by visiting the Madonie National Forest, some wineries & soak up the town's history.