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Big scenery, epic history, rich culture, amazing food and wine: this is road tripping at its very best. For us, Sicily encapsulates everything we love about road tripping: roads through big, beautiful landscapes, layers of visible history, a vivid cultural scene and, best of all, pasta and vino! Our own Sicily road trip was just shy of two weeks and we loved it.

With hindsight though, there are things we would do differently if we did the trip again. This is the result: a curated 2 week Sicily itinerary that takes on board our own learnings and experiences of exploring and driving in Sicily, and showcases the very best highlights around the island. How long does it take? This is a self-drive 14 Day Sicily itinerary. See further on for our suggestions if you have less time or more time. This post contains affiliate links. If you choose to purchase through these links we may receive a small commission, at no extra cost to you, which helps us to keep this website running.

Your support is very much appreciated! As this is a looping itinerary, you could also fly into Catania in the east, or Trapani in the west, and set out from either of those cities. Sicily sits at the heart of the Mediterranean, which means hot, dry summers and mild, wet winters. All of the overnight stops in this Sicily itinerary are in cities or decent-sized towns with a range of accommodation to suit various budgets and travel styles.

You can book accommodation for Sicily through all major booking engines. For this trip, we booked our accommodation through Booking. Just be ready for it, and drive defensively. Also, bring a car charger for your phone.