Sicily Road Trip: The Real Story of Driving the Island Ourselves

A first-person Sicily road trip: what it is really like to explore the island on your own, wrong turns and all.

I did not plan to fall in love with Sicily. I definitely did not plan to leave one of our stays a full day early. But I had convinced myself every place we booked was only one night. That is exactly how our Sicily road trip started. Looking back, that little mistake turned into one of my favorite parts of the whole thing.

We had just come down from the Amalfi Coast. We picked up a rental car in Palermo and set off to explore the island on our own. My husband Jim, our son Aaron, and me. Mainland Italy already had my heart after our Italy and Paris anniversary trip, but Sicily turned out to be its own kind of pull. No guide, no set schedule. Just the three of us and a car and a very loose plan. I will tell you right up front, that is not how most people should do Sicily. But it gave us the kind of trip I still think about.

A wrong turn that turned out right

Here is what happened. We had a place booked north of Palermo, right off the water near Sferracavallo, for two nights. Except in my head, it was one night. So we packed up and left and drove about an hour and a half toward Ragusa. Somewhere on that road it hit me: we had just given up a whole night we had already paid for.

Jim did not want to backtrack. So we did the only thing you can do. We pulled up a map and found a last-minute stay in a little coastal town called San Leone.

It ended up being one of the sweetest surprises of the trip. Our place was a two-story rental, and up on top where we were staying there was a balcony that looked right out over the water. It was less than a ten-minute walk down to the beach. The town was full of little restaurants and shops, the kind of spot you would never find on a rushed itinerary. The beach itself was not the cleanest, and there was some trash here and there. But the town had so much charm that I did not mind.

A Lemon Tree and No Common Language

The woman who owned the place did not speak a word of English. We talked with her entirely through a translation app on my phone. She had lemon trees right there in her gated courtyard, the one we pulled the car into and parked inside. And she insisted, absolutely insisted, that we take some home, picking five or six right off her tree. We were living out of a car. We only ate one or two and passed the rest along to someone else down the road. But I have never forgotten how kind she was.

The people are the thing I keep coming back to

That turned out to be the theme of Sicily for us. The people were some of the kindest we have ever met in Italy. The woman in San Leone set the tone. Back in Palermo, the owner of our place spoke no English either, but she could not have been warmer. Even strangers we passed on the street were kind. If you are staying in the smaller towns and not in a big hotel, that is what you should expect. Not much English, a whole lot of warmth, and a translation app that becomes your best friend. It became part of what I loved about the place.

“Not much English, a whole lot of warmth, and a translation app that becomes your best friend.”

One document check I was very glad we were ready for

Now let me tell you about the moment that could have gone very differently if we had not been prepared.

We were driving near where we had stayed outside Palermo, moving slowly through traffic. Two police officers stepped out in front of our car and waved us to stop. No lights, no pulling us over the way you would picture it back home. They just stopped us in the road.

They asked for everything. Jim’s international driving license, and all three of our passports. They took them, looked everything over, and after a few minutes handed it all back and sent us on our way. They were not rude, they were not unkind, they were doing their job. But it is a little scary in the moment. You are in a foreign country, handing all your documents to police on the side of the road.

Here is why I am telling you this. We were fine because we were ready. Jim had his international driving license, which you are required to have to drive in Italy. And we had our passports on us. I had read again and again that you should carry them in Italy at all times. If we had not had those things, I do not know how that stop would have gone. So if you take one practical thing from this Sicily road trip, let it be that one.

The place I picture when I think of Sicily

If you asked me to close my eyes and picture Sicily, I go straight to Castelmola.

It is a tiny village that sits way up high above Taormina. To get there you drive a series of hairpin switchback roads that climb and climb. Jim does not usually get rattled behind the wheel, but after going up and down those roads a couple of times he was done. He parked the car and said we were taking a bus or hiring a driver if we wanted to go back down to Taormina. He was not driving that road again. The next day we took the bus, and how those drivers handle those turns I will never understand, but they do it every single day.

Parking in Castelmola

There is one more thing about Castelmola worth knowing before you go. You cannot really park at your lodging up in the town. Our place was a small bed-and-breakfast with four or five rooms. Like most of the village, it had no parking of its own. You park in the town lots on the way up, set almost right along the edge of the cliff. Then you climb a lot of stairs to reach the town itself.

We were able to drive up just far enough to drop our luggage. After that, Jim took the car back down to one of those lots. Every time we wanted the car, it was about a fifteen-minute walk down to get it and back up again. That was part of why we were so happy to let the bus do the work. So if Castelmola makes your list, plan on parking below and walking up. Pack light enough to handle the stairs.

The reward for all that climbing is the view. Up at the very top of Castelmola are the ruins of an old castle, the Castello di Mola. When you stand up there you can see Taormina spread out below you, the coastline, the water, all of it. It is one of the prettiest things I saw in all of Sicily.

“It is one of the prettiest things I saw in all of Sicily.”

The town itself has such a cool vibe. Little winding streets, and cats everywhere. Jim was teasing Aaron that you cannot call an Italian cat with here kitty kitty. These are Italian cats, and they will not understand you. We had our last dinner in Sicily up there in Castelmola, at a little Italian restaurant. I had the best lasagna I think I have ever eaten. I am not much of a foodie, and I do not eat seafood at all. So for a meal to stay with me the way that one did, it had to be good.

More Stops on Our Sicily Road Trip

Castelmola was the moment that sticks, but it was not the only place that got me.

Agrigento and the Valley of the Temples was something to see. You stand next to those ancient Greek columns. They have stood there for thousands of years. It is the kind of thing that puts your own little life in perspective.

In Syracuse we spent time at the Tecnoparco Archimede, an open-air museum of Archimedes’ machines, and Aaron loved it. They had full-size reconstructions of these old machines, some of the earliest ever built. There were hands-on stations where you could try to work them yourself. He got such a kick out of it.

Then there was Ragusa, more inland than most of our stops. It had one of those pretty streets lined with colorful umbrellas strung overhead, like you see in a few Italian towns. Our rental there was, let me just say, an experience. The layout was so open that the tub sat right out in the bedroom behind a pane of glass, in full view of one of the beds. And it was the only shower in the place. When it was my turn to shower, we had to send Aaron into the one bedroom that actually had a door. It was odd, but it is one of those things we still laugh about.

And on a day trip from Palermo we drove over to Cefalu, and oh, I loved Cefalu. Such a pretty, welcoming little town right on the water. If I had it to do again, I would have booked a few nights right there.

The honest part I want you to hear from me

I will tell you the one thing that surprised me most, because I want to be real with you the way I would be with a friend. I always pictured Italy as spotless. Sicily was not. You would be driving along one of those narrow roads, the coast and the water opening up beside you. Then you would glance over. There would be a couch dumped on the roadside, or bags of trash, or a car seat somebody had pulled out and left behind. It was a shame, because the setting is so pretty. It is part of the real picture, and I would rather you hear it from me than be caught off guard.

How to Plan Your Sicily Road Trip

Here is my real advice, the kind I would give a client sitting across from me.

How you do Sicily depends on the trip you want. If you want to explore freely the way we did, rent a car and go. You get to wander from town to town on your own schedule. Thinking of pairing Sicily with the mainland? My Rome and Florence itinerary walks through the same rent-a-car-or-not question for that side of the country.

But most people will not be comfortable doing it exactly the way we did. English is scarce in the smaller towns, and public transportation on the island is limited. If that is you, I would set you up with a guided tour. It carries you through the different regions of Sicily and takes the driving and the language barrier off your plate. And if you only want to base yourself in one spot, say Palermo, Catania, or Taormina, you can skip the car altogether and be just fine.

When you are ready to start mapping out the practical side, the official Visit Sicily tourism site is a reasonable place to begin.

Was it worth it? Without a doubt. I would go back to Sicily in a heartbeat. We barely scratched the surface. We hardly saw Palermo, we did not see Catania at all, and there is so much of the island still left for me. I could spend a month there and not be done. Somehow, trash and wrong turns and roadside police stops and all, I fell for Sicily completely. I am not even sure I can fully explain why. Some places just get you.

If Sicily has been sitting on your someday list, let’s talk about what your version of it could look like. Maybe that is a rental car and an open map. Maybe it is a guided route with everything handled for you. Either way, I would love to help you build the trip that fits you.

Frequently Asked Questions About Sicily

Dreaming of your own Sicily trip? Let’s build the version that fits you.

Links to whisperingwillowtravel.com/consult

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