Sicily is a destination that in many ways we struggled to understand. It is naturally so rich but in practice so poor. We sadly conclude that the answer is the Mafia bleeding it dry and then some.
We spent a winter in Licata. It and Ragusa have sizeable winter liveaboard communities, but neither town is of any great beauty. Overall we found the island underwhelming. The east coast has Taormina, Catania, and Siracusa - all very beautiful visited from land, but only Siracusa worth visiting from the sea and even then the authorities are tedious in the extreme.
The south coast has little to recommend it, and almost no safe anchorages other than in the western corner. The coast faces south and the prevailing wind is westerly, so it is rolly everywhere.
We enjoyed the Aegadi Islands however, although the cruising permit is expensive enough for that to be rather a deterrent.