Two Month Sicily Roadtrip:
After spending April on mainland Italy, Barbie and I packed our bags and caught a flight from Bologna down to Palermo, Sicily. We deliberately timed our two-month Sicilian road trip for May and June to hit that perfect shoulder-season sweet spot.
Right now, we’re actually sitting at the airport in Catania, waiting for a flight to Naples for our final week in Italy before we head off to Turkey for a full summer of beach-hopping. Looking back, April through June is hands-down the absolute best time to visit Sicily. We completely avoided the notorious insane summer crowds and extreme heat of the high season, which, if you ask me, is a guarantee for a ‘not so pleasant’ experience.
If you can’t make spring work, September is your next best bet to beat the masses. Just a heads-up: pretty much everything in the beach towns shuts down from mid-October until late April, so skip those months unless you’re looking for cold weather isolation and closed restaurants.
Our strategy was simple: we spent a full week hunkered down in each town as we circled the island. Over my 30 years of backpacking and traveling the world, I’ve learned that packing too much shit into a single day and constantly jumping from hotel to hotel is a massive drain on your mental energy. It’s a one-way ticket to travel burnout.
Our newly adopted philosophy is all about going slow and easy. Lingering in one place for seven days gave us the freedom to wander, sleep in, and fully embrace the Italian siesta lifestyle. In Sicily, almost everything shuts down between 1:00 PM and 5:00 PM. It takes some getting used to, but it forces you to just sit still, relax, and experience a place exactly how the locals do.
The “Luigi” Restaurant Reservation Hack
The food in Sicily is out of this world, and we spent two straight months eating our asses off, filling our bellies with fresh seafood and pasta every single day.
Of course, making dinner reservations over the phone can be a bit tricky when you don’t speak the language. Over the years, I’ve developed a foolproof hack for the language barrier: I adopt a local name. In Mexico, I am always “Diego.” In Italy? My name is Luigi. A simple, single-syllable name that rolls off the tongue completely eliminates any confusion.
The phone calls always go exactly like this:
Me: Ciao, Lei parla inglese? (Hi, do you speak English?)
Restaurant: No.
Me: Ok, due persone alle otto per Luigi. (Ok, two people at eight for Luigi.)
Restaurant: Ok, Luigi!
Me: Grazie, prego!
Works like a charm every time.
We fully expected to pack on some serious weight with all this eating, but thankfully, almost every town we visited was incredibly pedestrian-friendly. Between all the walking and navigating the steep inclines in these historic towns, we managed to burn off most of the calories. We might still have added a pound or two, but I can confidently confirm that Barbie and I both left Sicily with buns of steel.
We also fell in love with the Passeggiata—the traditional early evening walk where the entire community comes out to catch up and shoot the shit before dinner. Everyone from the tiny newborns in strollers to the oldest nonne gets dressed up and hits the streets. The energy, especially on weekends, gives you such a great sense of local community.
Our Sicilian Route: The Destination Breakdown
The beauty of the roadtrip around the island of Sicily are all the incredible views while passing thru coastal towns and always being surrounded by fresh sea air and crystal clear blue/green sea water. Simply a relaxed and magical place.
Palermo, Cefalu, Castellammare del Golfo, San Vito Lo Capo, Trapani, Erice, Favignana Island, Agrigento, Noto, Marzamemi, Siracusa, Isle of Ortigia, Calabernardo, Catania.
We circled the largest island in the Mediterranean in a deliberate, leisurely loop. Below are the towns where we stayed and our thoughts of each town:
1. Palermo
We kicked things off by flying in from Bologna. You absolutely do not need a car here. We spent our week wandering the chaotic, vibrant alleyways of the city center and eating our way through the incredible street food markets. Palermo was a really cool city with great energy and a great city to walk around.
2. Cefalù
We took the train from Palermo to this sunny, relaxed beach town. Arriving here after a lot of heavy city travel on mainland Italy felt like a breath of fresh air. We had a killer Airbnb right on the seafront. Cefalù is a total must-visit during the warm months. No car is needed to enjoy Cefalu. We picked up our rental car the day before we left, specifically to take a day trip drive through the Madonie Mountains to explore the cool mountain town of Castelbuono. There are many cool mountain towns to visit and we chose to hang in and explore the town of Castelbueno.
3. Castellammare del Golfo
This place is a postcard-perfect small Sicilian town with a incredibly slow pace of life and a colorful marina packed with seafood joints. It served as our base to explore the many beaches in the Scopello area and the Riserva dello Zingaro. Our Airbnb was in the ultimate location right next to the town park (Villa Comunale Regina Margherita), making it a breeze to mosey down to the restaurants and our favorite gelato spot, Gelateria Vernaci. This town takes the afternoon siesta to a whole new level—it becomes a total ghost town between 1:00 PM and 4:00 PM. We loved this down time. It was our cue to follow suit and indulge in siesta time along with the locals, taking the most incredible power naps. Barbie never naps during the day, but this town’s chilled-out vibe knocked her out cold every afternoon.
4. San Vito Lo Capo
Even though it’s super close to Castellammare del Golfo, we wanted to hunker down here for a few nights just to enjoy one of Sicily’s best white-sand beaches and the ocean front coastal coves of nearby Macari.
5. Trapani
After the slow, sleepy beach vibes of San Vito and Castellammare del Golfo, hitting the faster pace of Trapani was a bit of a shock to the system. Luckily, we scored another winning Airbnb located directly on the sea, with our bedroom windows looking right out over Spiaggia delle Mura di Tramontana. Having those crisp spring sea breezes blowing through the giant windows was amazing—and having a phenomenal bakery (Oddo Michele Panificio) right downstairs was the absolute icing on the cake.
- Pro Tip: A must day trip. Take a short ferry ride over to Favignana Island for the day. Rent an electric bike and just cruise around the island exploring the hidden beach coves. Another fun day trip is taking the cable car straight up to the historic, misty medieval town of Erice to wander and eat along the walk.
6. Agrigento
The big draw here is the sweeping, unobstructed views of the valley and the sea that surround this town. The absolute highlight, though, was spending a day exploring the Valley of the Temples, a massive archeological site filled with incredibly preserved ancient Greek temples.
7. Noto
Noto is another cool, mellow town where you can just hunker down and wander around. The baroque architecture and cathedrals here are famous for a reason, and the town is packed with an awesome variety of food options, plus endless spots to down local gelatos and granitas. What makes Noto a good flashpacker base, though, is its accessibility to the ocean—it’s only a 15-minute drive to a ton of incredibly cool beaches inside the Riserva di Vendicari, not to mention the numerous surrounding beaches outside the reserve. While you’re based here, taking a day trip to the little Italian seaport hamlet of Marzamemi to have a long lunch and wander around is an absolute must.
8. Isle of Ortigia / Siracusa
We dropped off our rental car the second we arrived here because you can’t drive on this tiny island anyway. We spent a full week on this historic island doing a very strict routine: wandering the alleys, eating, walking the seafront, eating, shopping, catching a live Italian opera at the famous ancient outdoor Greek theatre… and then eating some more. It’s a magical place, but again, we caught it before the July/August rush. I can’t even imagine how packed these tiny alleyways get in the dead of summer. Consider yourself warned.
9. Calabernardo
For our final week, we picked up a fresh rental car in the nearby town of Siracusa and drove to a coastal Airbnb in Calabernardo. Let me tell you: there ain’t shit to do in Calabernardo, and that is exactly why we picked it. We spent the entire week just chilling on our deck overlooking the ocean and lounging on the wide white sands of Lido di Noto. It was the perfect way to wind down after two months on the road in Sicily. We celebrated our final night with an great meal at the famous Ristorante Manna Noto right near our place.
Next Stop: The Pizza Marathon of Naples
Now, we are trading the slow chilled out coastal life for the vibrant charm, modern grit, and chaotic energy of Naples. It’s time to shift gears and adapt to big city life. We have one goal, and one goal only for our final week in Italy: eat authentic pizza, pizza fritta, fried pasta, and fresh mozzarella every single day.
Big Doug & Barbie Drop Out of Society 
It seems like no matter how remote a place is, there’s lots of other folks who were looking for — and found — the same location. The temples and statues look like you’re in Athens! The Greeks were conquerers of the world! Beautiful sites and sceneries.
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