Traveling through the Straights of Messina is an interesting experience.
Approaching from the north, you pass the active volcano on Stromboli (a rock jutting out of the Tyrrenian Sea). The straights itself, is only 3.1km wide, and ships have to use a pilot to navigate through. Of course the area was settled by the Greeks as part of Magna Graecia. Syracusa on the Sicilan side and Reggio (Roman Rhegium, Greek Rhegion) on the Italian side. The Greeks originally settled Messina as Zancle (scythe), because of the shape of its natural harbor.
The Romans didin't pay much attention to Sicily until they began to reach beyond Latina. This expansion coincided with Greek and Carthiginian disagreements over control of Sicily. Ultimately, Rome was dragged into the first Punic War when they took the side of the Mammertines in Messina who had come under the control of a Carthaginian garrison. Three kilometers from Italy was too close for the Romans to tolerate, and the Senate eventully decided to oppose Carthage.