The 14-hour drive from Milan to Sicily is best taken in October, when weekend travelers trickle off the highways and the temperature drops into the pleasant high 60s. Beautiful sights are tucked behind Italian roads, and driving is the best way to see them. My husband, Ludovico, and I often do the trip in a weekend, but I suggest taking four or five days.
We usually leave Milan in the evening. Ludovico is a slightly unhinged driver who likes to zip through Northern Italy at 100 miles per hour, but I wouldn’t recommend that. Drive 90 minutes south before stopping for dinner in Emilia-Romagna, the heartland of prosciutto.