From the tip of Puglia to the western shores of Sicily, South Italy covers quite a long stretch. Add to that the lack of a good east west highway in the South (or most anywhere on the mountainous peninsula, for that matter) and the hassle of catching a ferry from Sicily to the mainland, and any trip across the Mezzogiorno takes a very long time indeed. I think it’s much more prudent to concentrate on either Puglia or the coast of Campania and on to Sicily in order to get the most out of your trip. I’ll focus on the latter one here. The trip from Rome to Naples is only about two hours on the highway as it’s pretty fast-moving traffic; it’s the bit south of Naples that is infinitely slower. It is also one of the most spectacular coastlines in the world. In fact, the whole coast down to the tip of Calabria includes some spectacular, well-known resorts: Maratea and Tropea, especially. The adventurous beach house seekers might turn up something very interesting down here. From Reggio, take the boat over to Sicily and explore the eastern coast: Siracusa, Catania and its volcano, and Taormina are the major points of interest. Just northwest, the Aeolian Islands are the highlight of any trip to Sicily in my opinion, with Stromboli as the crown jewel. From there, the northern coast to Palermo, in particular Cefalu, is studded with pleasant medieval towns, while Palermo itself will be one of the most unexpectedly magical cities you’ll visit in Italy.