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Chasing the sun

Coast-to-coast in Italy—275 kilometres by bicycle

By Georgios Vasilopoulos

July 2^nd, 2019

Chase the Sun Italia—the literature on their website promised a do-it-yourself event without rules, route signs or reward, other than accomplishing this remarkable feat. Cyclists of all abilities were beckoned to begin at sunrise from Cesenatico on the east coast of Italy. From there, participants would cycle through the heart of Tuscany to Tirrenia, where the sun dips beyond the horizon at the end of the day.

From its beginnings in 2008, when three ‘average cyclists’ rode coast-to-coast across the south of the UK, Chase the Sun has grown to attract hundreds of riders each year. The Italian edition has been running since 2017 and, this year, a second northern route was added from Tynemouth to Prestwick UK. All three events took place on the longest Saturday of the year, 22 June.

The 275-kilometre Italian event is arguably the most romantic of the three—across the coastal flats of Emilia-Romagna, through the mountains of Parco Nazionale Foreste Casentinesi, through Florence, Carmignano⁩, Vinci, Fucecchio and Bientina, over the mountain pass between Buti and Calci, down to Pisa and along the final stretch to Tirrenia. Add in a healthy dose of Italian sunshine, while soaking in the golden Tuscan countryside, and it’s understandable why more than 300 cyclists were seduced by the challenge this year.

One such rider was Federico Vandone Dell’Acqua. Fed is a 26-year-old photographer and avid cyclist from Milan who, with a bit of confidence-boosting encouragement from me, signed up a few days before the event.

“I found it a romantic and fascinating idea to ride coast-to-coast by bicycle, following the sun across some of the most beautiful landscapes in Italy,” Fed said. “I was curious about taking on an event that is iconic in the Italian cycling community and embracing a journey of this distance. I wanted to see if I could push my body and mind.”

Fed’s longest ride previously was a route running the circumference of Lake Como in Lombardy, northern Italy—175 kilometres and 1,700 metres of altitude, no small feat. But it wasn’t quite the 275 kilometres and 3,300 metres of altitude of Chase the Sun Italia.

Collecting his freshly tuned-up matte black Specialized Diverge Comp Carbon from the local bike shop, we loaded up the van. The van would play double-duty as our home and support vehicle for ‘Team Fed’ during the event. We set the GPS and aimed the van east.

The normally three-and-a-half hour journey to Cesenatico took nearly five hours due to the horrendous traffic around Milan and Bologna—too many people trying to get away for the first weekend of summer. It’s all about the little luxuries when parked on a motorway for more than five minutes at a time and, in this case, after several coffees and bottles of water, one of those luxuries was having an onboard toilet. It was a life-changing amenity in this context.

We arrived two hours late to 35°C heat and thick, humid air. The event hotel was a relic from the 1970s. We navigated the brightly painted, over-styled, kitsch corridors to the check-in table where Fed was assigned rider number 228, handed his goody bag and given an abridged orientation. We were quickly ushered to the restaurant where we sat opposite a lovely couple and their daughter. The excitable wife was ecstatic about her husband taking part.

Many of the other riders were already leaving but the restaurant was able to accommodate us, pushing through four courses in 20 minutes instead of two hours. The meal started with a delicious antipasto of insalata di polpo (octopus salad), moving on to a somewhat unremarkable first course of trofiette con zucchine e gamberetti (trofiette pasta with courgette and crayfish) and penne al ragù di verdure (penne with vegetable sauce), a beautiful second course of sogliola con pomodorini, olive e capperi (sole fish with cherry tomatoes, olives and capers), and ending with a dessert of mousse ghiacciata con coulis di frutti di bosco (frozen mousse with berry coulis).

We returned to the van and drove to the campground. Because we had to leave at 4:30am we were instructed to park up against the main road—not a promising location.

Final preparations for the day ahead

Final preparations for the day ahead

Final preparations for the day ahead

Fed carried out some last-minute maintenance on his bike, oiling the chain and putting the GPS in place, before having a quick shower and attempting to get some sleep before the big day.

Sleep proved challenging with cars and motorbikes racing up and down the road all night, and late-night revellers stumbling home at silly o’clock. When I did finally manage to nod off, the 4am alarm was right there, rudely commanding me to get up.

Fed ate some energy bars and gels and set off on his bike to the starting grid. I was close behind in the van.

Fed makes his way to the starting grid at 4:45am

Pre-rally jitters

Another energy bar

Pre-rally jitters

Sunrise breaks at the harbour in Cesenatico

A quick pose on the docks

One last photo before joining the starting grid

The atmosphere was much livelier than expected at this early hour, with more than 300 riders assembling themselves in the starting grid, and their friends and families lining the pavements. Some were excited, others anxious, but all were anticipating the enormous ride ahead.

Sunrise was breaking. Cinelli—a Milanese bicycle company and one of the main event sponsors—had a small team of riders taking part. The organisers were barking out commands so the event photographers could take a few snaps of them and the wider group before the start.

As the sun began to peek over the horizon, bathing the harbour in golden light, it was time for the rope to drop. The riders set off with cheers from the crowd.

The cyclists in the starting grid, anxious to get riding

Kilometre zero—the riders set off at 5:07am with determination

Returning to the van, the fanfare died down as the crowd dispersed, silence falling once again on Cesenatico. I programmed the first checkpoint—Bar Cavallino near San Godenzo—into the GPS, stopping briefly at Cesenatico’s Piazza Andrea Costa to capture one of the most beautiful sunrises I’ve witnessed firsthand to date.

Stunning sunrise at the wheel in Piazza Andrea Costa, Cesenatico

With my back to the sunrise, Via Roma was illuminated with the golden glow.

Via Roma, Cesenatico in the morning sun

Not wanting to interfere with the cyclists on the narrow backroads, I took the motorway to Forli, getting ahead of the group. I learned later that, by this time, one of cyclists was already out of the event, having bumped up against another rider and losing control, crashing into a ditch. He was injured and his bike damaged—a disappointing and premature end to the day.

Despite the event not being a race, competition was running high and some of the cyclists were going all out from the beginning, pushing beyond their limits, rather than pacing themselves for the long journey ahead.

As I reached Predappio—a small town with the dubious distinction of being the birthplace of Benito Mussolini—the first drops of rain started falling and the imposing Chiesa di Sant’Antonio loomed into view. Completed in 1934, the neo-Renaissance-style church was designed by Cesare Bazzani, one of the most prolific architects of public buildings during the early 20th century. The first stone was laid in 1931 with Mussolini’s wife Rachele in attendance.

Predappio remains to this day a site of pilgrimage for fascists.

Chiesa di Sant’Antonio, Predappio

From Predappio the road kept climbing. The drive took me through the small towns of Tontola, Strada San Zeno and Premilcuore as the rain came down with more and more verve. Piloting the 2.3-metre-wide ‘Enterprise’ along a 4-metre-wide, rain-slicked, twisty mountain road was somewhat less than ideal. But there was an element of excitement to it, and the scenery in Parco Nazionale Foreste Casentinesi was breathtaking.

Crossing from Emilia-Romangna into Tuscany, the rain stopped and the road widened marginally. I arrived at Bar Cavallino, the first checkpoint, at about 8am—an hour ahead of the riders.

A sliver of sun briefly peeked out from between the clouds

The car park overlooked a valley that offered panoramic views of the lush mountains. Bar Cavallino was run by an attentive, friendly couple. The husband was preparing trays of gorgeous focacce al prosciutto (ham sandwiches on unsalted Tuscan bread) while the wife was running around straightening out the chairs and wiping the tables outside—between smoking a generous number of rollies.

Rolling hills in eastern Tuscany

I ordered a caffè latte (culturally in Italy, it is only socially acceptable to drink caffè latte in the morning) with one of the sandwiches and a beautiful honey-filled pastry. I was absolutely famished, and the food was delicious. The couple were chatty and excited about the cyclists’ imminent arrival.

The Cinelli rep arrived and set up his tent to offer basic maintenance to the cyclists—and it wasn’t long before the first riders started to appear. Among the first 20 or so, Fed turned up wet but still smiling.

Kilometre 94—Fed arrives at the first checkpoint, smiling but wet

“It was so wet—I’m soaked!” Fed said. “So far it’s going really well. The beginning was a bit boring—flat and straight—and then it started raining. But once I got into the mountains it was amazing, although the roads were a bit slippery."

He was ecstatic—full of energy and excitement for the adventure ahead. After changing into dry socks and warming up for a few minutes, Fed ate a couple of sandwiches and had another energy gel. The bar was getting packed and he decided this was his cue to fill up his water bottles and carry on.

The local hound wonders what all the fuss is about

Posing at the first checkpoint

Posing at the first checkpoint

Ready to ride!

I got back on the road towards Florence. Despite leaving only a few minutes after Fed, it took about 20 minutes to catch up with him—the descent, with its sweeping curves, made for fast riding. We went our separate ways as I moved to the main roads towards the second checkpoint, Ristorate il Pinone near Verghereto, about 35 kilometres west of Florence.

The temperature had risen to the mid-30s and the hills leading up to il Pinone were steep and slow—I was grateful for being cocooned in the climate-controlled comfort of the van. I arrived at about 11:30am and parked among the trees in the upper car park. The lack of sleep the night before was catching up so I succumbed to a disco nap for about half an hour. The little luxuries aren’t just limited to onboard toilets—having a bed available while on the road can can be life-changing as well.

Behind the restaurant were dirt trails, and a number of mountain bikers were out and about braving the heat. A few took shade under the trees briefly, before disappearing off into the hills again. I could see on the tracker that Fed was only a few kilometres away, so I moved the van down opposite the restaurant.

View from the second checkpoint with the plains around Florence in the distance

Fed approaches the last corner before the second checkpoint

Final push to the second checkpoint

Kilometre 174—Fed arrives at the second checkpoint, Ristorante il Pinone

Those last few kilometres proved a challenge for Fed. He arrived 25 minutes later at about 12:40pm dripping with sweat and looking a bit unwell.

“It was so hot and humid. The hills were really tough—tougher than I imagined they would be,” he said before downing a bottle of water and towelling off the sweat. “But the downhill after the first checkpoint was incredible—so fast!”

After catching his breath we sat down outside the restaurant. Fed enjoyed polpette di maiale (pork and bread balls) and focaccia al prosciutto (ham sandwich) while I had a panino con la porchetta (bun filled with roast pork). We finished lunch with a shot of espresso.

“Okay. I’m ready to keep going,” Fed said, revitalised. He took a couple more energy gels.

The Cinelli rep arrived around 1:15pm as Fed was about to ride off—a bit of a boost for him as he knew he was well ahead of the pack.

Time to rehydrate

Tucking into an energy gel

A quick pose at the second checkpoint before carrying on

The next leg was comparatively less challenging, a 50 kilometre stretch with a fast descent from il Pinone and across the flats towards Bietina. I caught up with Fed briefly as he emerged from the hills and into Vinci, near the birthplace of Leonardo da Vinci. He was looking in much better spirits and flew past, without stopping, a big grin on his face.

Bar l’Angolo—the third checkpoint in Bietina—was in the middle of the town with no convenient place to stop or park. The farmers’ market was in full swing and the streets were lined with vendors. I eventually managed to find a space at the piazza not far away. It was now the hottest part of the day and the heat was oppressive, with not even a slight breeze to clear the air.

Fed arrived at 3:30pm and replenished with water and energy bars. Not wanting to hang about, he said he’d meet me at the fourth checkpoint and set off straight away.

Kilometre 224—Fed reaches Bar l’Angolo, Bietina, the third checkpoint

As I left Bietina, the road quickly became steep and narrow, with mirrors on many of the corners to check for oncoming traffic. Crawling my way up, the van’s motor laboured. I saw a pullout and waited for Fed to catch up in case he wanted some water.

“I can’t stop—I need to keep going and stay focussed,” he said as he rode by.

Non-stop climbing between the third and fourth checkpoints—no time to stop

I drove on to the fourth checkpoint at Ristorante i Cristalli in Prato a Ceragiola. This was the summit between Buti and Calci which had spectacular views of the flats below. Thankfully the altitude meant cooler temperatures and some respite from the infernal heat.

View from the fourth checkpoint with Bietina in the distance

The final push to the fourth checkpoint

The final push to the fourth checkpoint

The final push to the fourth checkpoint

Posing at the fourth checkpoint

Fed was only 30 minutes behind. He arrived at 4:45pm and looked fatigued. Topping up with water, he got himself a focaccia al prosciutto (yes, another ham sandwich—clearly the go-to snack in Tuscany) and sat down for a few minutes of rest and reflection. He had contemplated taking the alternative route, avoiding this final mountain pass. But this would have meant not having the stamp from the fourth checkpoint. After coming this far, he hadn’t wanted to give up.

“A few moments after I left Bietina, I felt like I was about to drop and couldn’t finish—my body was telling me I couldn’t do it, but I forced myself to keep pushing forward,” he said.

“It was hot, humid. I was hungry and dehydrated. My legs were fatigued and screaming at me to take the shortcut through the flats.

“I couldn’t bring myself to give up. I endured it and pushed on. The uphill was tough, yes, but cool and breezy. When I got on top of the hill it was so worth it—I feel really proud of myself.”

Kilometre 236—still smiling at the fourth checkpoint

Fed was looking a bit shaky, even after eating and rehydrating. I asked him several times if he was absolutely certain he was okay and he insisted he was. I urged him to take it easy on the last stretch—fast mountain roads and fatigue are not a good mix. It would be a devastating blow to have an incident after putting in so much effort to get to this point.

Promising to be extra attentive, Fed set off towards Pisa and the finish line.

Charred hills recovering from the Monte Serra wildfire which occurred on 25 September 2018

Leaving Ristorante i Cristalli, the landscape immediately changed to charred trees and destruction in the wake of the Monte Serra wildfire on 25 September 2018. But nature is resilient—many of the blackened trees were once again showing signs of life and the burnt ground was quickly becoming covered with greenery.

The roads were fast, with corner after corner snaking down the mountain though the rustic towns of Tiricella, Calci, Paduletto and Caprona to the flats around Pisa.

Blacked trees slowly showing signs of life

I arrived in Tirrenia around 6pm, squeezing the van into the cramped car park at Bagno Siria, a private social club. This was the final checkpoint and finish line of Chase the Sun Italia. No one was able to give me a definitive answer to whether I was actually allowed to park there so I put Fed’s Chase the Sun rider badge from his goody bag inside the windscreen and hoped for the best.

Due to a combination of fatigue and anticipation of post-event blues, Fed took his time in Pisa. He snapped some selfies at the leaning tower, and rode the last few kilometres to Tirrenia at a more leisurely pace—making the final leg of this incredible accomplishment last just a little bit longer.

Fed arrived with a huge smile on his face at 6:54pm—13 hours, 47 minutes and 4 seconds after leaving Cesenatico, averaging 24.9 km/hr moving and 20.2 km/hr overall. Total distance—275 kilometres with 3,300 metres of altitude, burning 6,560 calories. He got his stamp at the final checkpoint and, of course, the ubiquitous t-shirt.

We even ran into the same family from the restaurant the night before—the husband had made it as well, and the wife simply could not be happier about it, she was beaming.

Fed arrives at the final stretch

All smiles for the last few metres

At the final checkpoint

Fed gets his final stamp

Did the rally, got the t-shirt

The full booklet—all checkpoints stamped

Kilometre 275—a proud smile at the fifth checkpoint and finish line

Ready for the next challenge

After a refreshing dip in the Tyrrhenian Sea we joined the other riders for dinner. There were three antipasti dishes—the most gorgeous alici marinate (marinated anchovies) I’ve ever tasted, quinoa con cozze e vongole (quinoa with mussels and clams) and chou pastry with fish mousse. The first course of linguine con cozze (linguine with mussels) was also delicious.

By this point we were both fading quickly—Fed, of course, from burning more than 6,500 calories in a day and me from lack of sleep. We also didn’t have huge appetites, given the amount of food we’d both eaten throughout the day. With some regret we said our goodbyes and made a discreet exit.

The road to the campground went through the kind of place where you’d expect to find burnt out cars or bodies in shallow graves with the head, hands and feet chopped off. I asked Fed several times where he was directing us. When we arrived, however, we found ourselves in the most serene, quiet field with horses on one side and a lake on the other—absolute heaven for a good night’s sleep.

The next morning we stopped in town for some fruit and pastries for breakfast and set the GPS for Milan. We made one stop along the way at Recco to buy some Focaccia di Recco, a geographically protected, or IGP, specialty which is only produced in three bakeries in the area. The ingredients are flour, fresh cheese and olive oil—but the artisanal technique that brings these simple ingredients together into a delicacy is what makes it what it is. A crude way to describe it is two crêpes with cheese in the middle, but it is so much more than this—melt-in-the-mouth, gooey, crispy, moreish and absolutely delicious.

On the journey home, Fed had time to reflect on the day before.

“I’m so glad I did this,” he said. “Riding past the sights in Florence and Pisa on my bike while crossing the country coast-to-coast was something I never imagined I would do.

“I think my favourite sections were the downhills after checkpoints one (Bar Cavallino) and four (Ristorante i Cristalli)—being able to go fast and stretch my legs after the climbs was so energising and rewarding. I felt a sense of freedom and free-spiritedness, like there was no limit to where I could go on my bike.

“I feel proud that I didn’t give up after the third checkpoint and take the alternative flat route to avoid the last climb. In the end, while it wasn’t an easy event, it took less effort and strain than I thought it would.

“Chase the Sun Italia has motivated me to look out for more long-distance challenges in future. One day, perhaps, the Race Across America.

“People think that cycling is all about body, legs and physique. These things help, of course, but it’s 80 percent mind, focus and determination.”

And a little Italian sunshine.

More

Fed’s route

Footnotes

Writing, photography and post-production by George Vasilopoulos

FootNotes

Writing, photography and post-production by George Vasilopoulos

© 2026 Georgios Vasilopoulos

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