All Articles A 6-day road trip through Northern Sicily

A 6-day road trip through Northern Sicily

Embrace spontaneity on Sicily's winding roads.

Laura Delarato
By Laura DelaratoApr 19, 2024 9 minutes read
Skyline view of Palermo on a sunny day
Skyline view of Palermo on a sunny day
Image: FilippoBacci/Getty Images

Last summer, my boyfriend and I embarked on a six-day trip through Sicily’s winding roads. For months, I had been functioning like a robot—work, meetings, life—with no respite from New York City's rat race. The plan for our Sicilian road trip needed to be less structured and more spontaneous, allowing us to follow where the road and sea took us.

But it was more than pure relaxation that brought us to Sicily. My grandmother, who grew up in Naples, often regaled me with stories of our family in Italy, painting vivid pictures of sun-kissed relatives enjoying pasta dinners and late nights under the Italian moon. A seasoned traveler, she adventured well into her 70s and always wanted to return to Italy and its islands, particularly Sicily, to explore its cuisine and landscapes as her mother had described. Unfortunately, she never realized these dreams before she passed in 2021.

Our voyage became a tribute to embracing spontaneity and confronting the unknown—to the places my grandmother never saw, the gelato she never tasted, and the beaches she never swam in. It was a thrilling adventure of exploration and self-discovery, where intuition served as my guide.

Each day unfolded with new marvels and escapades, from the quaint fisheries of Isola delle Femmine to the awe-inspiring views of Taormina. Here, our unforgettable journey through the heart and soul of Sicily—and how you can follow our route.

Tip: When you’re picking up your rental car, opt for the smallest available rental (as long as it fits your luggage). The roads can get narrow, especially in Sicily's smaller towns like Taormina, and parking, let alone driving, can be tricky with a big rig.


DAY ONE

Total mileage: 14 miles

Pizza at Antica Pizzeria la Punta
Outdoor dining at Antica Pizzeria la Punta
Left: Pizza at Antica Pizzeria la Punta, Right: Outdoor dining at Antica Pizzeria la Punta
Image: Management/Tripadvisor

EVENING: Settling into Sicily

Once we disembarked from the plane at Palermo’s airport and secured our rental car, we drove for 40 minutes into Bellacera to reach our Airbnb. Our first stop, though, was an Esso gas station off Strada Statale 113 to load up a full tank of gas (il pieno, per favore) before heading to Casetta Bianca. This laid-back spot, just a minute's drive from the gas station, offered pizza and pasta with friendly service and a terrace overlooking the sea. We sat there with a bit of "wow, we made it" stare on our faces as we bit into a plain slice of pizza.

While the rest of our trip would be spent in hotels, we were eager to spend our first night in an actual home, which is why we chose this spot off the beaten path. The host’s family, along with their dog, greeted us at the gate with a plate of ricotta and pan-fried steak with basil. We soon found ourselves on the top floor of the family home, offering views of both mountains and the sea simultaneously—a real welcome to the country.

DAY TWO

Total mileage: 100 miles

Beach at San Vito Lo Capo with Mount Monaco in the distance
Beach at San Vito Lo Capo, Italy
Image: David C Tomlinson/Getty Images

MORNING: Head to the beach

Our first destination was 20 minutes away at the Lido del Carabiniere, a tucked-away beach frequented by police officers and their families, with a public section available for a fee. We paid around 30 euros for access to a chair of our choice, a charming pebble beach, crystal-clear waters, and rocky reefs. We had two options: sunbathe on lounge chairs above the water with easier access to restrooms and the snack bar, or sit in beach chairs on the sand with the water occasionally lapping at our toes. We opted for the latter, enjoying the sea glass and watching Sicilian children wade into the water.

Tip: Roads to the beach get very narrow. Upon arrival, resist the urge to venture down the tight driveway. Instead, park on the street alongside other cars and stroll down to the entrance gate.

EVENING: All about the pizza

To wrap up our first day, we stopped by Pizzeria La Punta, a bustling upscale pizza joint offering seafood-infused pies and stunning waterfront views. While this spot has temporarily closed, nearby Pizzeria D'Anna Di Paolo D'Anna and Casetta Bianca offer an equally inviting spirit perfect for unwinding after a day at the beach. Note: Typical Sicilian pizzas, like the ones you’ll find at these restaurants, will be more of a thick sponge crust and meatless sauce.

Where to stay:

Worthy detours along the way

DAY THREE

Total mileage: 106 miles

View of Levanzo island in the Mediterranean
View of Levanzo island in the Mediterranean sea west of Sicily, Italy
Image: EleSi/Getty I mages

MORNING: Breakfast and folklore in Isola delle Femmine

A quick note: while this day may seem long, the drive from stop to stop is not as daunting as it appears on the map. We kicked off our day with a short drive from Bellacera to Porticello, making a pit stop at Le Delizie for a quick morning espresso fix and some cookies—cassate, pizzelle, and cornetti—to tide us over to breakfast. Our route, which took us around the outskirts of Palermo, offered glimpses of scenic hiking spots like Pizzo Sferrovecchio and Pizzo Manolfo from the car window—but we were laser-focused on getting to the town of Isola delle Femmine, so we didn’t stop.

The fishing haven sits just across the water from an island of the same name, home to intriguing ancient lore, including stories of a women's prison and Turkish girls shipwrecked on its shores. You’ll need to hire a boat to visit the island itself, but we simply stopped for breakfast and views from the mainland. At Bar Pasticceria Valentina, I enjoyed a Sicilian breakfast with granita con brioche, taking in the bustling ferry port. We then strolled around, passing Italclam, the local shellfish shop, and Cascino Fiori, the town florist, before getting back in the car to drive to Rocce Isola delle Femmine—a tourist hotspot where you can walk along the rocks and sand toward the crashing water's edge. Its breathtaking scenery justifies the visit.

AFTERNOON: A beach day straight out of a dream

Then it’s back in the car for a staggering route that passes olive oil groves and towns like Buseto Palizzolo and Custonaci. Our destination: San Vito Lo Capo—a one-way-in, one-way-out beach town—just an hour away.

Spiaggia San Vito Lo Capo epitomizes a quintessential Italian beach, with its crystal-clear waters and rows of orange umbrellas, all sheltered by Mount Monaco in the distance. For around 40 euros, we rented two lounge chairs and basked in the sun, relaxing until the sun set. Before leaving the town, we grabbed some takeaway arancini and drinks from Sfrigola, a renowned local chain, and savored them on the steps of the white-and-green checkered Marinella Square.

EVENING: Gelato and pizza

Driving back, we worked out way through Castelluzzo, stumbling upon Bar Gelateria Case Vacanza La Giara and treating ourselves to pistachio gelato and a cannoli. Then, it was off to our hotel in Trapani: Central Gallery Rooms inside Palazzo D'Alì Staiti XIX. Once settled, we changed out of our beach attire and strolled to Amici Miei for some pizzas—the quattro gusti, a pie with cooked ham, artichokes, mushrooms, black olives along with the standard tomato and mozzarella, was a personal favorite—before retiring after an eventful day.

Where to stay:

Worthy detours along the way

DAY FOUR

Total Mileage: 0 miles

Aerial view of Pretoria Fountain in Palermo
Aerial view of Pretoria Fountain in Palermo, Sicily, Italy
Image: FilippoBacci/Getty Images

MORNING: Pre-ferry breakfast

Every road trip deserves a designated break from driving, and so we swapped our rental car for exploration by foot and ferry. For espresso, we stopped by San Lorenzo Café, about a 10-minute walk from the hotel. It makes for a great place to people-watch, as older men and nonnas wander the street or gather at the San Lorenzo Cathedral across the road.

Then, it was off to the Trapani Ferry Port for a day trip to the serene Levanzo, one of the tranquil Aegadian Islands. Equipped with pre-booked tickets on the Ferry Hopper app, we boarded for the 50-minute journey. It’s a brisk ride with a few wavy bumps to Levanzo—there were a few times when I felt my stomach in my throat. And while I'm not a person who gets seasick, I did see a few people hammering water and Dramamine as we made our way across the strait.

Tip: Everything in the app is marked in military time, so be diligent in planning your time when you get off the boat (and give yourself a buffer when it’s time to board again).

AFTERNOON: Finding connection in Levanzo

I’ve wanted to visit Levanzo ever since I read an article from Italy Segreta, an Italian culture magazine, that aligned the island with my zodiac sign (Pisces). It described how the island lacks paved streets and exists in its own world, much like Pisces with their heads in the clouds. This struck a chord, as it was a feeling my grandmother always recognized and nurtured in me. So when I saw the pastel-hued homes and the local boats in the harbor and the waves crashing against the rocks welcoming the ferry upon arrival, my eyes welled up with tears.

This colorful little island in the Med felt like a sanctuary. After exploring the main street of Via Calvario, we took a stroll along the shoreline, carrying our water shoes (a must on the island's rocky beaches) and spare clothes. Once we made it to the Spiaggia di Cala Fredda, we took a dip in the admittedly chilly water and enjoyed the natural beauty around us. After we basked in the sun's warmth, we savored aperitivos, olives, and caprese sandwiches at Panetteria La Chicca, a laid-back local haunt, anticipating our return ferry to Trapani and the comfort of our awaiting beds.

Where to stay:

Worthy detours along the way

DAY FIVE

Total mileage: 66 miles

Elevated view of Piazza Bellini in Palermo city, on the left side Santa Maria dell'Ammiraglio and on the right side Chiesa di San Cataldo
Historical city centre of Palermo in Sicily, Italy
Image: Sergio Formoso/Getty Images

MORNING: Pastries and ocean views

Today, we're retracing our steps along northern Sicily back towards Palermo, Sicily's bustling capital. Sure, we could have cut through more of inland Sicily to see the country—but we opted to double back along the coastline so we could take in the ocean views again.

AFTERNOON: A walk through Palermo

Our first stop in Palermo was the Ficus di Villa Garibaldi—also known as The Strangler Tree—a century-old Moreton Bay fig in Piazza Mariana, regarded as the largest tree in Europe. Its immense size provided rare shade from the scorching Sicilian sun. (If you happen to visit on a Sunday, you'll find a flea market bustling around the piazza.) Then, we found Edizioni Precarie, a paper store that recycles Palermo's street market wrapping paper into writing kits, which made for the perfect souvenir.

For lunch, we headed to La Majolica for delicious panini and creamy gelatos at Dolce Capo, a small shop nearby with a singular artisan at the helm and a line that snakes around the block. The amarena and pistachio with whipped cream on top was heavenly and well worth the wait.

EVENING: A Mediterranean feast

We chose to take a cab back to our hotel (the Hotel Giardino Inglese) because our legs were tired. After settling in, we showered and started packing for our journey to Taormina—but we couldn't leave Palermo without a final meal at Bioesserì Palermo for quintessentially Sicilian Mediterranean dishes like insalata di gamberi (shrimp salad) and seppie e piselli (cuttlefish with peas). (If you’re looking for a walk before dinner, wander through the Parco Giochi Giardino Inglese, which stays open til 5 p.m.)

Where to stay:

Worthy detours along the way

DAY SIX

Total mileage: 181 miles

Tourists walking around the Piazza of Taormina and San Giuseppe Church
San Giuseppe Church and Piazza of Taormina
Image: Renata Tyburczy/Getty Images

MORNING: Witnessing a centuries-old tradition

If we had our bathing suits handy and not at the bottom of our suitcases, we might have been tempted to swim in Tre Piscine, a rocky cove with calm water, on our drive back north. Instead, we stopped at the Tommy Todaro ceramics shop, known for its refined Moors headpieces—a symbol of Sicilian luck. Then, we made a refueling stop at Bar Baronetto, a classic Italian gem for arancini and drinks.

Next, we drove 82 miles to Messina, the closest point to mainland Italy on our Sicilian journey. We parked near a local gelato spot, Perigolosi, before walking through the square of Piazza Duomo. Here, you’ll find the grand Astronomical Clock of the Cathedral of Messina, featuring biblical and mechanical figures as well as clock faces, a moon, a planetarium clock, and a perpetual calendar. We were too late to witness but every day at noon the clock's statues come to life, replaying biblical and allegorical scenes across the tower.

EVENING: A big night in Taormina

Onto the final leg of our adventure: Taormina. The roads were as windy, uphill, and narrow as they say, so be prepared. Yet, despite the ascent, the views persisted, even as the sun began to set. Our destination for the night was Hotel Villa Ducale, perched in the hillside's narrow ridges above the town.

Once settled, we collapsed into bed, eager to conserve energy for our night out. Recharged, we hopped onto the hotel's shuttle down to the main thoroughfare, Corso Umberto—a bustling hub of shopping, dining, and nightlife. We kicked off the night at Duomo di Taormina—more of a fortress than a cathedral—where I lit a candle in memory of my grandmother.

As we meandered towards dinner, temptation loomed—tote bags, peperoncino charms, and magnets beckoning from every corner. La Cantina del Sole proved a delightful spot for sampling wines to bring home as souvenirs.

Then, it was on to dinner at I Giardini di Babilonia, a tucked-away seafood and pasta oasis. Dinner concluded predictably, with a gelato pilgrimage to Le Delizie di Elianna, which served up the creamiest pistachio gelato I had the whole trip.

Satiated by food, wine, and gelato, we awaited the hotel shuttle back at the front of Corso Umberto to ferry us back up to our rooms. The next day, we'd journey to Catania for our flight back to New York, but for now, we savored our last moments in Sicily.

Where to stay:

Worthy detours along the way