We flew into Palermo, spent one night there, then drove across the northern coast for 4 days, staying in various small towns ending with 2 days in Catania.
The drive is nice, though some of the towns are on top of crazy steep hills! And driving in towns can be nuts with really narrow streets and locals with no regard for rules or lanes.
Mount Etna is a good 1/2 day trip from Catania. We drove to the base, took the gondola up, then got on the shuttle that takes you as near to the summit as allowed. From there, you can walk around a couple calderas but you are no longer allowed to climb to the active crater. It is definitely worth paying the extra for the gondola and shuttle - we saw a lot of students and such taking the cheaper option of walking it, but it's truly not worth it between the heat , the boring scenery and the dust. of course, if you're going in winter, bundle up - the top will be freezing cold (it may even be a full ski hill right now). I was ther ein the summer, it was 38C in Catania and about 15C up top with snow still present.
Since you're a history guy, I'd definitely recommend 2+ days in Palermo - so much history there and it shows in the architecture and city lay out.
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