The Quiet Between The Chaos: Picking Up On The Sicily Divide

“The climb began gently, politely even, the sort that lets you believe you’re still in control. ”

The climb began gently, politely even, the sort that lets you believe you’re still in control. Then, without ceremony, it steepened. The gravel turned pale and loose, the air thinned just enough to be annoying, and the landscape opened out into wide, green silence. Sicily stopped posing for photographs and started asking questions of our legs.

Ahead, the ribbon of dirt had the colour of crushed biscuit. To the sides were sheep pasture, a few stubborn pines, and that particular Sicilian green that makes you question everything you’ve ever said about winter riding being bleak. The air was 17 degrees, warm in the sun, cool in the shade, the sort of temperature that makes you feel like your riding hero. The sort that convinces you you definitely packed the right layers and not, say, an entire wardrobe for emotional comfort.

I turn to Alexa to see a face of struggle, she is more used to riding horses than bikes but our eyes connect for long enough to return smiles even though it’s tough - she’s enjoying herself too. I consider saying something, but my lungs have retired so I get my head down and plough in the lowest gear I have. And somewhere in the background of my wheezing, a second thought arrived. It’s funny that this all started with an airport not long ago.

Not a dramatic ferry crossing or a misty sunrise over a cobbled piazza. Just Palermo, breezy and efficient, with more flights than you’d expect and none of the faff you’d normally associate with transporting an entire bicycle through Europe. We had the kind of itinerary that looks glamorous on Instagram and feels like a spreadsheet in real life, only a few days between work commitments, which meant we had to compress what most people savour over a week into something closer to a long weekend.

“There was a running commentary on Sicily that somehow included football, food, and an opinion on every town we passed. We told him we wanted to see the south, and he took it as his personal mission.”

So we did what any sensible people do, when attempting to ride the length of an island. We immediately got in a taxi. Our taxi driver from the airport set the tone right away. He was the sort of friendly that makes you feel you’ve known him for years, despite him having met you approximately twelve minutes ago. There were hand gestures, lots of help carrying our bikes and no shortage of recommendations. There was a running commentary on Sicily that somehow included football, food, and an opinion on every town we passed. We told him we wanted to see the south, and he took it as his personal mission.

By late evening we were in Sciacca, a hill town with the Mediterranean spread out beneath it like a well-behaved postcard. We stayed in a boutique hotel perched above the water, and the next morning the first light hit the sea with that soft, golden kindness usually reserved for romantic comedies. Sciacca itself sits on the slope in layers, tiled roofs, pastel walls, little balconies, as if the town is leaning forward to see what the ocean is up to today. Sicily has a habit of doing that. Presenting itself neatly when you arrive, then revealing its true personality once you start moving through it.

Our plan, ambitious and possibly unwise, took inspiration from the Sicily Divide. A remote mix of gravel and road that carves down through the interior where tourism thins out and the island feels less curated. Sicily is the largest island in the Mediterranean, and it has been a crossroads for just about everyone with a fleet and a plan. Greeks, Romans, Arabs, Normans. The layers show up in architecture, language, and, crucially, what ends up on your plate. You can taste history here. Sometimes literally, if you’re careless around a particularly generous bakery.

We aimed for a deliberate 50-50 mix of road and gravel. The wild quiet of farm tracks through sheep country, broken up by sweeping, alpine style tarmac that curls around valleys like it’s enjoying itself. On those road sections we’d hear it before we’d see it, the gentle rattling approach of a 1990s Fiat Panda doing 23 kilometres an hour and apparently having the time of its life. It would pass with a supportive and sympathetic wave, reminding us we’re far from the bustle of cities and towns now.

The interior was all rolling hills in full flourish. Lush fields, orange trees, olive groves, the kind of green I’d have previously associated more with northern England than this close to Africa. In summer, Sicily can be brutally hot. In this shoulder season it was, for my tastes, perfect. Warm enough to feel alive. Cool enough to keep moving. The sun had that low winter angle that makes everything look more impressive, including your own mediocre climbing technique.

We’d roll into mountain top villages that seemed to operate at a different speed, as if someone had quietly turned the world’s volume down. There were cafés with proper coffee, small, strong, and served with the casual competence of people who’ve been making it correctly for centuries. We’d sit and watch locals preparing for a food festival. Tables being hauled out, decorations going up, a mild chaos unfolding with an underlying calm. It was both relaxing and slightly frantic, which we were beginning to realise was the very epitome of what Sicily is all about.

The friendliness was constant, and it wasn’t the performative kind. People were curious about the bikes, the bags, the obvious question of why two tourists in tight clothing would choose to pedal through the middle of nowhere in winter. Alexa had the unfair advantage of growing up with Italian, which made every interaction warmer and easier, although even she kept catching the edges of the local dialect, which is spoken as much as standard Italian in these quiet villages. Sicily is closer to Tunisia than it is to Milan, and you feel it in the light, in the wind, and in the way the island refuses to be only one thing.

And then, inevitably, the brutal hills reminded us who was in charge. Sicily is relentlessly lumpy. The kind of terrain that doesn’t give you one heroic climb and then reward you with an afternoon of flat smugness. It’s up, down, up again. Much of the gravel is steep enough to be character building, always engaging but Sicily pays you back in panoramas that quickly make you forget the struggles before.

By the time we reached Catania, the contrast was almost comical. After days of quiet tracks and sleepy villages, arriving into the island’s second largest city was overwhelming. Bustling, chaotic, vibrant, loud. Traffic flows like water that’s been told to hurry up. It was fun in the way that only slightly stressful things can be, a reminder that Sicily isn’t only empty roads and pastoral calm.

From there, the pilgrimage felt inevitable. A trip to Sicily doesn’t feel complete without pointing your bike towards Mount Etna. It’s Europe’s highest active volcano, and it dominates the eastern skyline with the casual confidence of something that is still, technically, making new land. The climb is long and steady, the sort you settle into, and then suddenly you’re riding through black lava fields, snow dusted rock, and the eerie beauty of a landscape that looks freshly invented. Exchanges with locals revealed however, Etna is revered, not feared here. Despite numerous devastating eruptions throughout history, she is seen as a provider — bringing fertile soils, volcanic-filtered water, a milder climate, always keeping a watchful eye on its people.

On our day, the mountain was doing what it does. Erupting. Not in a Hollywood panic, but in that quietly astonishing way where you can see a plume rising only a few kilometres from the road and realise you’re watching geology happen in real time. You stop, of course. You stare. You try to take a photo that will never capture the true scale of it, grateful to experience mother nature while out on a bike ride. The descent was the kind that resets your brain. Nearly 2000 metres back down to sea level, a ribbon of smooth road unfurling forever, the air gradually providing much-needed warmth with every minute of downhill. It went on and on, matched by an everlasting sunset that seemed determined to escort us all the way back to Catania.

By the end, Sicily had done what it does best. It had been generous. With landscapes, with people, with food, with that strange mix of calm and chaos that makes a place feel alive rather than staged. And in winter especially, it’s hard to think of many riding destinations that offer this much. Rolling green hills, quiet gravel, chunky climbs, and a live volcano for good measure.

Sicily feels like the epitome of loveletter from Italy, the version people imagine in the movies, except it’s for real, and it makes you work for it which, in cycling terms, is the highest compliment I can offer.