If you are wondering how to get to Sicily, what to see first, how to move around, where to lodge and all that. You get to Sicily by plane connecting mainly through Rome and Milan even though there are several companies flying directly from abroad.
There are ferries from Naples (10-hour journey) and from Cagliari and Genoa. Driving down from Calabria it is quite a long drive. It depends on how much time you've got. Remember there is no bridge in Messina.
Once you get there, you should be able to see the main land destinations in a couple of weeks. It may be convenient for you to focus on the West Side of the island, if you land in Palermo and on the East Side when landing to Catania airport. Rent a car! Do not rely too much on public transports. They are OK for moving between one town and the other but once at destination it is not easy reaching the right spot.
As far as the island resorts are concerned, it is possible to take ferries from Palermo to Ustica and to the Eolie. Rent sailing boats if you have more time, it really is worth. The Eolie can also be reached from the coast of Messina. Ferries also depart from Trapani and Ustica for the Egadi Island. Pantelleria can be reached by ferry from Trapani and by plane. There are ferries serving the Pelagie from Porto Empedocle (Agrigrento).
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