Small Tour in Sicily, Taormina, Agrigento, Marsala

Easy to do on your own. No need to bother with travel agents, most of whom don't know what they are doing.
Since you plan to go outside of major cities and towns, maybe a car is preferable.
CTA is close to Taormina, PMO is closer to Marsala, Agrigento is a distance from both. If you have never been to Sicily, I suggest including also other important destinations in your trip. Sicily has a lot to see, therefore a week may be too short. In your shoes I would concentrate with Sicily for the two weeks and leave Abruzzo for another time. You might also combine a day or two in Rome at the beginning and ending of your trip. The only major airline that goes to Sicily is Alitalia, and coming from the US you'd be stuck with only that airline. But if you stay in Rome a day upon arrival and a day or two before departing you can take advantages of the numerous low cost airlines that fly to Sicily from Rome.
For Sicily's ideas see below:
www.bestofsicily.com
Also the Pescara airport has no connections to either Rome or Milan Malpensa, it is mainly a low cost airport for Ryanair. Therefore to fly back to the US you'd need to drive or take a bus/train to Rome and fly from there.

It eould be difficult for me to leave Sicily after a week. Palermo has many things to see and is a convenient base for trips to Monreale, Segesta, and Erice (which you could visit on a stop in Trapani on your way to Marsala). Agrigento, Cefalu, Siracusa, Taormina - not to mention the islands off the coast.

Good suggestion to fly in and out of Rome to make a less expensive and less time-consuming connection.

Another major airline flying from the US to Sicily is Lufthansa. I am flying soon from JFK to Munich, connecting to a direct flight from Munich to Palermo on Air Dolomiti, which is a Lufthansa regional airline. Maybe you could do this out of Boston instead of jFK.

I had the experience of flying from Roma to Catania and made my way up and down the eastern coast of Sicily using public transportation.
It was wonderful to stay in Taormina multiple nights. The town is lovely. There were having a film festival when I was there in the month of June and I got to watch a film from a screen in the amphitheater. I also took a day trip (via tour bus) to Agrigento which also included a stop at the Villa del Casale at Piazza Armerina. It was an early morning departure and took all day. Since this was over 5 years ago, the roads might be better and transportation times place to place might be quicker.
It was really easy to sign up for a tour in Taormina and I'm sure a hotel there can guide you so you might want to contact them ahead of arrival and see what they would suggest. I found buses sometimes problematic. If you get a car, you'll have more freedom to come and go when you want.
Easy to fly from Catania back to Rome.

In Taomina I used legendofsicily.com for both of my stays, in the Eastern side of Sicily. I rented an apartment and took a day-tour with them. I went to both Mt. Etna and a winery and loved it. The second time I rented a bnb also through this website..

Rick's Sicily tour itinerary will give you an idea of about the fastest way that you can circumnavigate Sicily in 10 days. More time would be more relaxing, if you're doing your own driving. I would not particularly have any qualms about driving, although the tour guide I traveled with last year recommended buses. The latest Lonely Planet guidebook to Sicily was published in January, 2014 and has more info than their all-Italy book.

Thanks for all these helpful replies. I will look into all the responses and see what happens. I have an Italian pen-pal in the town of Tromello which is about 1 hour south of Milan. I want to somehow spend an afternoon with him at least. We've been talking back and forth for well over a year.

I also have a "virtual" friend in Frankfurt Germany I'd love to meet up with for an afternoon. Somehow, if I plan this right, I may fly in and fly out in a way that allows this to happen. It's logistically hard for me to understand. But, I've got a year to go so time to plan it all out.