Rome & Sicily travel to Palermo

It sounds like you only have 7 full days on the ground (or even a bit less than 7?). That is not enough time to stretch yourself geographically, and to try to sample Italy AND Sicily because you'll eat up a lot of time transport (Sicily itself is worth more than 10 days alone). With 7 days total, I would pick 2 cities max (Rome and Florence would be a good example) and maybe one smaller city side trip from either city if you're really ambitious. Remember that you will likely be jet lagged the first day(s) so you're not going to be in top shape. That's why it's not worth overplanning and trying to do too much with so little time. You can easily even stick to Rome the entire 7 days (plus maybe a side trip or two) if you want to take it slow.

If you want to start in Rome and end, say, in Milan, it may be worthwhile to fly back home from Milan so you don't have to backtrack (so that's a multi-city flight as opposed to a straight round-trip). Sometimes this options works and sometimes it's just too expensive or time-consuming - you have to actually price out the flights when the time comes to see what's best.

I agree with Agnes that you are stretching yourself too thin. The simple logistics of changing locations takes up an enormous amount of time that it is hard to imagine until it is experienced. With your seven day timeframe, you should choose to spend your time in only one or two cities. I also agree that flying what is called open jaws, or to put it more simply, landing in one city and returning from another will save you time that you can use for sightseeing.

Take a look at this -- https://www.ricksteves.com/tours/italy/venice-florence-rome--- to see how ( overly) ambitious your proposals are.
If 7 ( ?) nights is all you have, 2 destinations is really all you can do.

Have you purchased a guide book to aid you in your search?

So very helpful. Thank you everyone. Agree with all of you, It was a bit over ambitious. Sicily seems to be a Must Do for our first trip to Italy. And I really don’t want to drag luggage through the entire trip.
We’ve been told to start with Rome. It looks like a plane to Sicily from Naples. And if we need to add one more day. Then it’s 8 days total.
I do have a book on Rome. Not one on Sicily, yet.

Still looking for Rome and Sicily hotels. And recommendations for seeing either Palermo vs Catania.

You could fly Delta or Alitalia to Palermo and spend the whole week in Sicily. You'd pretty much have to be willing to drive and it would pretty much have to be at a cooler time of year unless you really like heat. But we survived being there in July (17 years ago). Spring would be great.

We stayed for a week in Sicily in one agriturismo near Enna and one B&B west of Palermo, drove all around the island easily, and hardly saw half of even the major things there are to see in Sicily. We plan to go back.

From reading and watching Rick Steves for years, I had expected Rome to be all crazy, Naples to be crazier still, and Sicily to be completely wild and crazy. I have found none of these places to be crazy, and in fact that the farther south we go in Italy, the more sweet and calm and friendly things are --- perhaps due to fewer tourists.

What do you like? Food? Wine? Ancient Roman and Greek sites? Baroque architecture? The countryside? Scenery? Mosaics? Street markets? Church art and architecture? Beaches? Ceramics? Hill towns? Gelato? A volcano? Sicily has all of these and more.

If you haven't watched the Italian TV series Montalbano yet, get out the first few DVDs at you local library --- they are wonderful and set in Sicily. Or read the books. They will make you want to spend at least a week in Sicily!

Well one thing to keep in mind is that Palermo is not representative of Sicily, it's just its largest most congested city (but it in one of the 2 main entry points for flights, the other being Catania). If you limit yourself to Palermo only, you'll get a very skewed sense of Sicily (most of it is so much more laid back and rural). It would be like visiting NYC and thinking that's what the US is all about (not to say both cities aren't well worth visiting). I'm not sure you realize how little 7 days is, and how much there is to see in Rome and the (mainland) Italy. I would disregard where people are telling you to go as a "must" and make your own trip based on your own interests...but you'll have to do some background research first and figure out where you really want to go. If Sicily is genuinely a "must" for you, consider just doing Sicily for 7 days and keep it manageable (meaning stick to one region and not try to see the entire island)

I'll just agree with everyone else, and emphasize that you should listen to their advice, or you'll be sorry!

In seven days, you can see a tiny part of mainland Italy, or a bigger part of Sicily. You cannot "see Italy" or "see Sicily" in that time, and you certainly cannot see both! Accept these limitations now, or, again, you'll be miserable.

Why do you say "Sicily is a must"? If you can tell us that, we can help you plan better. It's not a typical place to see on a first trip, but it's wonderful, so if that's where you want to go, then make that your trip.

I agree with nancyscherer8, that descriptions of Palermo as "Naples on crack" were completely inaccurate. I did find Naples a bit stressful, but neither Rome or Palermo seemed "difficult" to me, coming from New York; coming from Chicago, I think you'll be similarly prepared.

If you want to see the smaller, more laid back Sicily, consider flying into Comiso Airport which is not far from the towns of Ragusa, Modica, and Noto - all of which are delightful. That Southeast Sicily/ Hyblean Mountain/ Val di Noto region is full of smaller Baroque towns with lots of things to see. The largest city is Siracusa and it's a fantastic stop. All the towns are well linked along a single train route, so it's not hard to get around provided you can deal with the train or bus schedules. Unfortunately, Comiso is a small airport so the only flights to it from Italy are from Rome and Milan; there are no international flights that will get you there.

Here's a good website of Sicily to get you started - ignore all the loud ads, I know they're annoying. The Palermo region is also a fine choice but it's just a larger busier city, that's all. Each region is Sicily is different and has much to offer.
http://www.bestofsicily.com/sights.htm
http://www.bestofsicily.com/roadmap.htm

If you like Agnes's ideas of places to see in Sicily but can't make it work with a flight into Comiso, you can fly into Catania. While Palermo is a larger city, Catania is the largest airport in Sicily, with more flight options than the others. Furthermore, the airport has direct bus service to all kinds of places in eastern Sicily, without needing to change in downtown Catania (if you're not renting a car). If you are renting a car, the Catania airport will have a large selection, which is particularly useful if you need an automatic.