Climbing Sicily – An Adventure to Remember-Oct 2025

Climbing Sicily – An Adventure to Remember

In early October, four couples set out for a climbing trip to Sicily,-Kameans, Zitrons, Schwartzes, Vainers – joined by four guides: Albi,  Alesandro,Carlo and  for the first  time Marco , who is local — to explore the island, its wild cliffs, sparkling seas, and volcanic landscapes.

We landed in Palermo, dove straight into the city’s pulse, and wandered through its lively market, filled with shouting vendors, fresh fish, and the irresistible smell of fried arancini. The Norman-Arab Cathedral, standing proudly above it all, reminded us that Sicily has seen many civilizations and rulers.

From there, we drove west towards Trapani to  Parco degli Aromi Hotel , a serene hilltop hotel surrounded by lavender, rosemary, and thyme. The views stretched endlessly over the Mediterranean and Mt Cofano and at sunset, the air filled with the scent of  sea breeze.

San Vito Lo Capo – Cliffs, Sea, and Grit

Our first climb was a multi-pitch route on Monte Monaco, rising directly above the turquoise water. The limestone was grippy  yet very jagged and sun-warmed, the scenery beautiful . After climbing and rappelling down , Reg slipped on loose scree and fell a few feet, breaking her collarbone. But in true Reg fashion, she stayed calm, tough, and determined — continuing the trip despite the pain.She’s tough!

After  the climb  we gathered at San Vito Lo Capo, a laid-back beach town, where we toasted the day with Aperol spritzes, wine , cheeses and cold cuts .

The next day brought a ridge climb with sweeping coastal views — but the descent was quite  brutal, a mix of steep scree and dense, thorny bushes that clawed at us the whole way down. Scratched, dusty, and laughing, we ended the day at a beach side restaurant in San Vito, eating sea food and delicious sicilian dishes , like caponata .And of course Cannoli!

Capo Calavà – Roadside to Sea Cliffs

From San Vito we drove toward Milazzo, stopping at Capo Calavà for a unique route that began right off the road, rappelling down the cliff toward the sea before climbing back up. The views were spectacular, but midway through the route Jeff slipped, injuring his heel and back. He was grounded for a few days but handled it with grit  â€” a theme for this whole resilient crew.

Lipari and the Aeolian Islands

From Milazzo, we took the ferry  to Lipari, where we spent 2 nights at Villa Augustus .We  climbed by the sea —on the west coast , with panoramic views of the surrounding islands.we also took a dip into the sea. In the distance, Stromboli volcano had faint columns of smoke, a reminder that this whole region is  volcanic .

But then the real adventure began.

La Canna di Filicudi – The Heart of the Journey

A zodiac boat carried two couples and three guides to La Canna di Filicudi, a dramatic volcanic spire rising nearly 70 meters straight out of the Tyrrhenian Sea. Two other couples stayed behind on Filicudi — recovering from injuries and a persistent virus — while we ventured out.

The sea  luckily was calm, but the landing was treacherous. There’s no dock — only slippery, slimy -covered rock at the base — and getting from the rocking boat onto the wall required timing, nerve, and a helping hand. From there, the climb was raw, exhilarating, and unpredictable, with loose rock, and the endless blue stretching beneath our feet.There was very little beta about this climb.

At the summit stood a small Madonna statue, arms open to the sea. We stood beside her in silence, overwhelmed — wind whipping, hearts pounding.

The descent was no less intense: the boat pitched with the waves as we climbed back in/ Later, we learned that only about thirty people have ever climbed La Canna, due to the fact that it is a protected area and  also the only home of the black Filicudi lizard, a rare species that lives nowhere else on Earth 

Adding to the magic, Alessandro flew his drone, capturing stunning aerial footage of the climb — the rock tower glowing  against the deep blue water.

Chaos, Grit, and Kindness

While we climbed, Albi was on his own adventure. He had left his wallet on  the remote Lipari beach, ( where we climbed earlier on)realized it too late, and somehow managed to retrieve it — taking the hydrofoil solo and rejoining the group just in time for the Canna climb-on his own .

Meanwhile, a virus made its way through the group — first Jeff, then Nicole, and finally Tami. But no one complained. Reg, despite her broken collarbone (and future surgery), smiled through it all. Jeff K was an exemplary husband, tending to Reg with calm devotion. And Tami, who two years ago said she’d never climb at all, stood on top of La Canna, wind in her hair and pride in her eyes.

Etna and Taormina – The Grand Finale

After Filicudi, we returned to Milazzo and drove south to Taormina, where we had dinner at a lively restaurant — delicious pasta, local wine, and a band playing songs from The Godfather. It was very much  touristy, but charming and joyful in its own way.We had excellent fish there.

Then came Jeff’s turn for trouble: after recovering from his heel injury, he discovered that his passport was still on Filicudi. Miraculously, it was found and sent by ferry to Milazzo, where Carlo, one of our guides, drove all the way from Taormina to retrieve it. That’s dedication.

The next day took us to the slopes of Mount Etna, where Jeff K arranged for us to visit visited a  winery- Cantine Tornatore in Castiglione di Sicilia , tasting  reds and crisp whites grown in volcanic soil. Learned about the local grape, Nerello Mascalese.  Then, in a veyy large and rugged 4x4s, we made our way towards the top of Mt Etna.  climbed higher until snow appeared on the ground. We hiked the final stretch to the crater , surrounded by snow,cold wind, fog, and a landscape that felt like another planet.

On our last day, we climbed above Taormina and took a scenic boat tour along the coast. That’s when Tami finally caught the virus — the last twist in a trip already full of them.

Sunday morning came early. The group headed home from Catania, while Lori and I continued to Naples.

Reflections

It was a trip that tested everyone — full of injuries, lost items, viruses, and wild moments — but also laughter, courage, and unforgettable beauty. The food and wine were incredible — pasta with pistachio cream, grilled fish, caponata, pizza and cannolis that no one could resist.

Through every challenge, our guides were phenomenal — calm, patient, endlessly professional. They inspired confidence even on the sharp limestone of Monte Monaco and the slippery basalt of La Canna.

Sicily gave us everything — beauty, chaos, friendship, and adventure.

A journey none of us will ever forget.