I’ve been been meaning to cycle the circumference of Sicily for a couple of years and this summer I finally had the opportunity. I was originally going to do it over four days, sleeping on beaches at night, but with my time running out here I would have to do it in 48 hours riding non-stop. It’s pretty much bang on 1000km around the perimeter with over 8000 metres of climbing, a tough course but possible to do in two days at a decent pace.

My friend Chris Herbert “The Barbarian” heard what I was planning and came out to Sicily to join me. Chris was fresh from London-Edinburgh-London where he finished up second and a very experienced endurance cyclist. My previous longest ride was the Kingston Wheelers 300km audax Amesbury Amble, so this would be a trip into the unknown and I was thankful to have Chris along for the ride.

On planning the route, I discovered there is an audax every two years Sicilia No Stop, so we used their route, however we would start from Catania and ride clockwise (senso orario) down towards Syracusa. Some said this was the tougher way to ride it, but I was keen to do it this way around as the second half from Palermo to Catania would be a much more scenic (but very hilly) return leg. I had split the route into four parts, roughly equating to 12 hours each… two days and two nights of riding.

Part 1: Catania to Gela

We started Thursday morning at 8.20am from the Castello Ursino in Catania and headed out on the coast road towards Syracusa. It is the least scenic part of the route with a huge oil refinery at Augusta that looks like something out of Mad Max. There was a lovely tail wind and we were soon setting a blistering pace on the aero bars, ticking along with an average of 30kph. It took four hours to reach Sicily’s most south easterly point, the fishing village of Portopalo, which sits parallel to Tunis.

After heading inland to Ipsica, we then got back on the coast road and slap bang into a head wind that dropped our average speed. Nevertheless we reached the town of Gela and the end of the first part of the route after 9 hours, several hours ahead of schedule. At this point I boldly claimed that we could be back in 40 hours (how misguided that would turn out to be).

After some refreshments in Gela at Harry’s Bar – I tried to blag the drinks free without luck – we set off into the sunset for our first night of riding. At this point I was getting some jip from my left knee from riding pretty hard on the aero bars for several hours – I hadn’t had much time to test and tweak the setup. Chris was also suffering with his left knee after a pretty bruising ride a few weeks before at LEL. Elements of doubt started to creep in and I wondered if we would be totally wrecked by Palermo.

Part 2: Gela to Trapini

The road out of town was pretty busy but we were well lit and staying right and cars were giving us plenty of space. We were riding on the hoods and in the drops, avoiding the aero bars to rest the knees and give us more control in the dark. I was starting to feel the tiredness in the legs after 10 solid hours of riding, but decided to settle in best I could and tapped out a steady pace. Agrigento looked spectacular with its ancient Greek temples that equal those of Athens, lit up on the hillside in the dark.

After Agrigento, my knee was starting to feel really sore, so we stopped at a pharmacy at 9pm to buy some Neurofen. I must have looked a bit of state after 12 hours on the bike as I got some funny looks from the pharmacists. We found a bar down the road and loaded up on pizza, cokes and espresso. I drink a fair bit of coffee, but I found myself having an espresso at every stop as I was feeling turbo charged after each one, but I was worried about getting too wired and not being able to nap.

We reached Sciacca at midnight, over 15 and a half hours in and stopped again as Chris was after some Red Bull. I had my final espresso of the evening, then we broke out our stash of Bounce Balls and got ready for the final few hours of night riding. When we left the town the route broke off from the main road, the SS115 which we’d been following and started winding its way through unlit B roads, It was really slow going as the road was full of pot holes and seemingly heading up and over every hill available. It was also getting very chilly, cold enough to freeze the balls off a brass monkey by Sicilian standards and we layered up with gilets and jackets.

We finally reached Marsala 460km in at 4.30am after 20 hours of riding, both feeling pretty knackered after a tough section of road. We sat down in a piazza for a while, enjoying the warmth of the town before setting off for Trapani which would bring us to the end of the second part of the route. The road to Trapini headed through cultivated fields which weren’t holding any warm air and it was bloody freezing! It was a 30km dead straight Roman road that seemed to be never ending. After an hour and a quarter the lights of Trapini came into view and we entered the outskirts of the city. We could see the lights of Erice up on the hill and tried to ignore the fact that we would need to climb over that in a few hours.

Chris was getting very sleepy and we pulled into a petrol station so he could sit for 5 minutes and stare into the lights. I was buzzing from caffeine but I could feel the tiredness creeping in and I was trying not to yawn. We carried on to the centre of town, now just under half way at 490km. For lack of a better option, we pulled in at another petrol station and took out our down jackets and lay down on the concrete for 15 minutes. I closed my eyes and thought about my warm bed and started to question what the hell I was doing, with still another 500km left to ride. Something bit me on the arse and Chris stirred and announced what a great sleep it was and I half-heartedly agreed, although I did strangely feel more awake and less fuzzy.

Part 3: Trapini to Santo Stefano di Camastra

As the sun came up we rode out of town and straight onto a massive climb. Chris seemed to be full of energy spinning away up the climb, whereas I was totally wrecked and was having to get out of the saddle just to keep my momentum going. After waiting for me at a roundabout he broke the news that it was 30km to the beach at San Vito Lo Capo, with a massive hill to climb both there and back. Minchia!

I spotted a bar and shouted to Chris to stop as I was desperate for some solid food after a night eating bars and gels. Chris must have thought it was curtains for me at this point and let me know he thought we wouldn’t make the 48-hour limit. I realised I had been looking pretty messed, but I knew it was just a lull and said to Chris we can do it. He looked doubtful but agreed we’d give it our best shot. We had a rollò con wurstel, the closest thing you get to a sausage roll in Sicily and I immediately felt a lot better. With the sun up I was feeling more positive and we carried onto the beach with a new vigour, enjoying the long descent after the climb. After 24 hours, we had hit 527km, over half way but with a shedload of climbing to come.

Down at the beach I had some more food, a cornetto (croissant in Italian) and yet another espresso and then we headed back up the climb, tapping out a nice rhythm and getting back to the top after 1 hour of climbing. By this point the sun was fully up and it looked set to be another hot day. I was in my element in this weather, but it was hot for Chris who by now had pretty salty kit and was starting to get some chafing.

We headed around the coast on some beautiful roads, admiring the views of the Mediterranean Sea to our left and mountains to our right. After 30 hours riding and 640km in, we reached Palermo at 1pm. As I suspected, it was a fairly manic cycle through the city… the driving is chaos and we had a couple of near misses with cars bombing onto roundabouts or pushing into our lanes. There were lots of shouts of “JESUS CHRIST!” from us. I said to Chris let’s find a decent spot for lunch then get the hell out of there. We spotted a bar and pulled up for a plate of pasta, cokes, and then I got a second course of meatballs, caponata and potatoes, and of course all washed down with another espresso. When I went to pay I realised we were out of cash and they wouldn’t take card. Chris went off to find a cash point and finally returned over 30 minutes later after touring the broken cashpoints of Palermo. I’d wanted to leave at 2pm and we were behind schedule, losing around an hour. It took an age to get out of Palermo, navigating our way slowly out of the snarled-up traffic and finally got back on the open road.

There were beautiful coastal roads after Palermo and I resolved to enjoy the last of the day’s sun. My knee pain was gone and I felt great, tapping out a steady pace on the front, trying not to push it too hard on the rolling hills. As the sun began to go down we reached Cefalù with a stunning pink sunset along the coast. As we were rolling through a coastal town Chris pulled up and suggested we split up as his knee was giving him pain on the climbs and he was having to accelerate over the top of every climb to catch up with me. We were going the same route so I suspected we would see each other again on the road.

We touched fists and then I road on up the road, keeping an eye on the clock. There would be 12 hours to complete the last 260km, which should in theory be easy, but with a long night ride ahead I wasn’t counting my chickens. Although it was a long way to go, after riding the best part of 1000km I felt pretty serene and chilled with what was to come. With the sun fully down it was very dark on the country roads and I had to stop for a while to sort out my lights, at which point Chris passed me. I must have stopped for about 10-15 minutes messing around with my kit before carrying on.

Part 4: Santo Stefano di Camastra to Catania

I reached Santo Stefano di Camastra where the fourth part of the route was due to start at around 7pm, after 34 and half hours riding. I loaded it up on the Garmin and continued in the dark.

The roads were fast and my main lights were cutting out, as I was struggling to charge them whilst riding as one had a dodgy connection and another couldn’t be charged whilst in use. I felt quite exposed just using my back-up blinky lights and I was pretty relieved when I caught Chris and we were better lit up together on the road.

We rode on together reaching Capo d’Orlando, on a rolling and windy coastal road full of false flats, ramps and descents. It was a pretty knackering profile and by this point our pace had dropped right down. We stopped for a rest in Patti around 11pm and went into a bar for espresso. I was feeling really spaced out in the bar, as if I was drunk, and had a laugh chatting with the locals about what we were doing.

We pushed on in the dark and Chris’ pace had dropped right down, and he was struggling with his knee. I kept the pace down to stick together but I had one eye on the clock and making it back for 48 hours. I knew that once I got to Messina it would be a quick dash home on home roads that I know well. Somewhere along the coast before Messina I looked back and Chris was gone. I backtracked down the road and found him sat on a wall stretching out his knee, he was in some discomfort and urged me to push on. He would try to ride to Messina and sleep or get a train to Catania.

I rode on solo into the night, with my front light out of action I couldn’t see a thing on the dark country lanes. I was picking a line down the centre of the road hoping to avoid pot holes and praying for the best. Outside of Messina I entered a little village called Sparta and shouted “MADNESS? THIS IS SPARTA!” Moments later a big white dog came bounding towards me out of the darkness looking for a cyclist dinner. I promptly shat myself and sprinted away as fast as my legs would allow, at which point the battery pack charging my light flew from my bike onto the road. I stopped up the road for a couple of minutes before quietly returning, being careful not to freewheel to find the battery pack. A funny few minutes.

Down the road I reached Torre Faro, Sicily’s most north easterly point. I had now touched all three corners of the island. I felt a few drops of rain so I got my jacket out of my bag into my jersey pocket and loaded up my pockets with food and caffeine gels for the final part of the journey. On reaching Messina there were only 100km left, with 4.5 hours to ride them, but I was feeling totally screwed and struggling to keep any kind of decent pace. I headed through town getting some funny looks and comments from locals. On the main drag there was a traffic light every 100 metres which would turn red as soon as I reached it, so I duly jumped every single one and got back on the strada statale to head down the coast towards Taormina.

The drops of rain had now turned into a steady shower so I pulled my jacket on and kept heading down the coast. At some point I got stopped by the carabiniere who asked me if it was wise to be cycling at this time of the night in the rain? I garbled something in Italian about circumnavigating the island in 48 hours and he replied “ciao ciao” and turned away. Malaka!

The villages I past through had street lamps, but when I reach Taormina I was riding in the pitch black with my blinky light showing none of the road. There was a pretty nasty decent in the rain, where I started to question my own sanity. With the sleep deprivation taking full effect I was hallucinating big time, and every plant was turning into a person or an animal. I was trying to call Maria Grazia to get her to bring a change of clothes to Catania, but my phone was working in the rain.

After a brutal climb to Taormina I was back on familiar roads heading towards Catania, however everything looked different and at times I wondered if I was heading the wrong way. My body was racked with pain and my knee was sore again, I was finding it hard to apply pressure on the pedals. The last 50km just didn’t seem to be moving on the Garmin and every km seemed to talk 10 minutes to tick by.

Around Giarre I hit a cobbled section of the road and I was yelping on each pedal stroke and had to jump onto the pavement to keep going. Our house is just up the road from here and it took a lot of willpower to keep going and not turn off and head to a warm bed. At 5am people were driving ridiculously fast to head to work and I gave the finger to several drivers who pulled out in front of me or cut me up. At Acireale the road to Catania becomes quite busy and I was getting properly sleepy, trying to hold a straight line and see it home.

The rain had stopped and at 7am the sun came up with another beautiful ink sky. I crawled into the city and joined a bike path, probably looking a proper state slumped on the aero bars with other cyclists giving me a wide berth. At 7.50am I reached the finish point Etoile d’Or, after 47.5 hours on the bike and with half an hour to spare. I stuck on my down jacket and took a selfie. Maria Grazia had been following Chris on the Spot tracker and arrived 10 minutes later along with Chris himself. He had slept at Messina and then clawed back time on me to finish only 10-15 minutes later. Chapeau!

It was a pretty incredible ride, but mentally it was the toughest thing I’ve done. I’m still suffering the after effects with numb fingers and a trapped nerve in my back. I think it will be a while before I attempt another 1000 and next time I will bring better kit. Big thanks to Chris for teaching me the ways of the #prohobo life.

The ride on Strava – https://www.strava.com/activities/1250126086