Last September, eight of us rented a boat and sailed around the coast of Sicily and up into the Aeolian Islands.
We started at Agrigento and hiked around ancient ruins...moved around the southern coast to Syracusa, probably the coolest large town on all of Sicily...then to Taormina, the touristy but charming town up on the hill.
We slept on the boat, and ate most meals on-shore. Every morning started with an espresso/cappucino dingy run to the local village. Not a fan of canoli? Then you haven't had it in Sicily.
Anxious to get to the far reaches, we sailed through the Straights of Messina toward the Aeolian Islands. Much of our route was the area Homer wrote about in The Odyssey. Amazing to think that the geography was identical to ancient times many of us read about in college!
The islands were incredible...each one with its own personality. Great restaurants and historic sites. One heads-up: beware of the scary-looking "medusa" jellyfish with long freaky tentacles. Their sting hurts like a )*^^_-)*&er...but the lasting scar is kind of cool.... A few of us continued on to the mainland of Italy...Rome, Florence, Pisa, Lucca, and Cinque Terre before flying to London from Genoa.
See below for a big tip here: