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Sicily in October

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We will be in Sicily October 14th through the 22nd. We will fly into Rome, and then down to Catania. I am an air line employee, so we will be travelling standby, doing a ZED fare on Alitalia, so we would like to keep our travel plans flexible. Destinations we are considering are Messina (visiting the Aeolian Islands), Taormina, Syracuse (Ortygia), and possibly Catania.

Our plan is to rent a car from Catania, and drive up and down the east coast, and explore the towns along the way. For accomodations we will book as we go, online, either through airbnb.com, or hotels.com.

Is there something I'm leaving out of this plan? A town, a must-see destination? Should I skip any of the aforementioned destinations in favor of another? My wife is a serial shopper, and loves gardens, beaches, and history.

Also, how difficult would it be to deal with a car with a plan like this? Obviously, parking is the most important consideration.

Any advice is appreciated.

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