Exploring Sicily: Must-See Towns and Hidden Gems

Sicily had long called my name — a land steeped in history, sun-drenched coastlines, and postcard-worthy towns perched on hillsides. In March, I finally answered that call. I mapped out a 10-night road trip, starting and ending in Palermo, circling the island clockwise. What followed was a blur of ancient ruins, long lunches by the sea, winding roads through olive groves, and the kind of charm that only Italy can deliver.

Whether you’re planning your own Sicilian getaway or dreaming from afar, here’s the full itinerary with hotel recs, favorite moments, and packing must-haves to help you plan.

🚗 Getting There + The Car Rental Tip

Flying into Palermo, I picked up a sprightly little Fiat 500 — the kind of car that fits the winding, narrow streets of Sicily like a glove. If you’re visiting during high season, definitely book in advance. And don’t forget an International Driver’s License — rental companies will ask for it.

Driving was smoother than expected. Most towns had parking just outside their centers, which meant I explore on foot — espresso in hand, always.

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🏛️ Palermo (3 Nights)

I started the trip in Palermo, and the city greeted me like an old soul — layered, complex, and utterly enchanting. Crumbling Baroque facades peeked out between colorful market stalls. Street food vendors selling spremuto d’arancia next to centuries-old churches. It’s a place that moves to its own rhythm.

For the first three nights, I stayed at Open Sicily Rooms — a great, budget-friendly choice in the historical district. The host was warm and welcoming, the location ideal for exploring on foot, and there was even a luggage locker available at checkout which made things super easy.

One morning, I discovered I Segreti del Chiostro — a hidden café inside a former monastery. I sat there with a warm cannoli and rich espresso, surrounded by faded frescoes and sunlight pouring through stone arches. One of those quiet, unforgettable moments.

Palermo’s Catacombs were something else — rows of real mummified bodies lining the walls. Haunting, yes. But also a reminder of how deeply the past still lingers here.

🏞️ Monreale (Day Trip)

Leaving Palermo, I made a detour to Monreale — a hilltop town with a cathedral that took my breath away. Inside, golden Byzantine mosaics shimmer from every corner. Outside, sweeping views of the valley below make the climb well worth it.

⛰️ Corleone (Drive-Through Stop)

On the drive toward Agrigento, I passed through Corleone, made infamous by mafia legends. I didn’t stop for long, but the mood was cinematic — winding roads, misty hills, and a kind of gravity in the air.

🌅 San Leone / Agrigento (2 Nights)

My next stop was San Leone, a sleepy beach town that felt like a hidden pocket of calm. I’d wake up to the sound of waves, grab a cappuccino, and then head to nearby Agrigento.

Seeing the Valley of the Temples at sunset was like stepping into another era. The ruins blazed gold against a pink sky — pure magic. On the coast, I climbed the surreal white cliffs of the Turkish Steps (Scala dei Turchi), where the sea sparkled turquoise and the wind carried stories.

🍫 Ragusa (1 Night)

Driving into Ragusa felt like arriving on a film set. I stayed at Centodici Rooms, a stylish spot just steps from the baroque beauty of Ragusa Ibla.

Before checking in, we popped into a local grocery shop and stocked up on everything delicious — salamis, cheeses, olives, bread, and fruit — for the ultimate Sicilian picnic in the room.

I wandered cobbled alleys, stumbled upon secret courtyards, and admired views that stretched forever.

🍦 Modica & Siracusa (Drive-Through Stops)

We left Ragusa in the morning and drove through Modica and Siracusa on the same day, en route to Catania. Modica is known for its Aztec-style chocolate — grainy, rich, and completely addictive. I didn’t get the full chocolate experience this time, but it’s definitely worth a proper stop if you can. We did make a few quick stops in local shops to taste and learn about the chocolate, and I even brought some home. If you’re not used to the grainy texture, I melted it down with dark chocolate to make chocolate-covered berries after the trip — a delicious way to extend the memories.

Siracusa was a quick seaside stop — just enough time for a caffe affogato (one of many I had during the trip, alongside countless tiramisus). It had a breezy charm and beautiful waterfront views, and I was happy we got to pass through without needing to do more.

🏙️ Catania (1 Night)

Catania was a quick overnight, but it had its charms. I checked into Archimede Suites, where breakfast is delivered to your room — a luxurious little touch. The room itself was spacious and beautifully designed.

Catania feels a bit grittier than other Sicilian cities, so be selective about where you stay. Still, it’s the perfect jumping-off point for Mount Etna.

🌋 Mount Etna

Even though the cable car was closed due to strong winds, I wasn’t about to miss Mount Etna. I took the bus up to the volcano, but honestly, it wasn’t worth the €50. If it’s windy and you’re not planning to hike, I’d say skip it. The cable car might have offered a unique experience. However, the bus ride didn’t add much to the adventure. This was particularly true given the price. The wind was freezing and howled like something out of mythology — not exactly the breathtaking experience I had hoped for.

But being that close to a living volcano? Unreal. Just make sure to bring real gear:

🏔️ Taormina (2 Nights)

If Sicily were a fairy tale, Taormina would be the setting. Perched high above the Ionian Sea, it’s all terraced gardens, winding streets, and balconies dripping with bougainvillea.

I toured the Four Seasons San Domenico Palace — yes, the White Lotus hotel — and stood in the Cecilie Suite dreaming. Modern luxe wrapped inside a historic monastery. Pure fantasy.

Taormina is for slowing down. I lingered over granitas and coffee, browsed handmade ceramics, and watched Mount Etna smolder in the distance as the sky turned rose gold.

🏖️ Cefalù (2 Nights)

By the time I reached Cefalù, I was ready to pause. This seaside town is the definition of charm — a crescent beach, medieval streets, and an easy pace that makes you want to stay forever. The weather was warm when we arrived. Sicilys unique location on the African plate bring warm winds from the neighboring continent.

I split my stay between the artsy Bohemian Guest House and sleek Sunset Hotel Cefalù. Both offered different moods, but shared one thing: unforgettable views.

Evenings were for slow walks along the sand, gelato in hand. One night, I drove into the hills to Castelbuono — a sleepy town where I had one of the best dinners of the trip and picked up a legendary Fiasconaro panettone to bring home.

🛫 Back to Palermo (1 Night)

I returned to Palermo for one last night before my early flight. It was quiet — just dinner, a glass of wine, and time to take in all that Sicily had given me. Magic, truly. My home base was the elegant Palazzo del Poeta, tucked inside an 18th-century palace. The rooms had artistic flair and a stillness I craved after long days exploring. We also returned here for our very last night in Sicily — a quiet evening and the simple comfort of enjoying our leftovers in bed while watching Netflix. It felt like the perfect closing scene to a magical journey.

Final Thoughts + What I’d Pack Again

March was perfect — spring blossoms, quiet streets, and cooler temps in the mountains. If you’re packing, keep it layered and chic:

👜 Travel wardrobe picks:

Also helpful: I loaded up a Visa gift card ahead of time to avoid foreign transaction fees — a great little travel hack.

And don’t worry about over-planning. Sicily has a way of guiding you.

❌ What I’d Skip Next Time

As magical as the island is, a few spots didn’t quite live up to the hype for me:

Corleone – While iconic in name, it lacked the charm or attractions that made me want to linger. If you’re short on time, this drive-through stop can be skipped.
Catania (for more than a night) – Unless you’re planning an excursion to Mount Etna, Catania didn’t feel as captivating as other towns. Gritty and industrial, it lacked the warm charm I found elsewhere.

💡 Bonus Tips: Road Tripping Sicily

Book hotels with free parking (or ask about it ahead of time). Many charming town centers are ZTLs (limited traffic zones), so it’s best to park just outside and walk in.
Don’t stress about the itinerary being perfect — I ended up booking all of my stays last-minute while on the road, and those nights turned out to be some of the best.
Gas stations aren’t always open late, especially in smaller towns, so top off your tank earlier in the day.
Cash still matters in small bakeries, cafés, and toll booths. Keep some euros on hand.
Download offline maps (Google Maps lets you do this), especially if you’re venturing into rural areas with spotty reception.
Enjoy the unexpected. A wrong turn led me to a bakery that handed me warm sfincione from the oven. Those are the moments that stay with you.