The same waiter who served us last night looks at me through dead black eyes, him up at 4am to serve breakfast, me just about awake enough to eat it. I give him a buongiorno to indicate I am no threat – with mini cereals and individual yogurts already laid out, I shall ask nothing of this man but coffee. He smiles like a sad tiger prawn in a bow tie.

Outside the sun is yet to rise and it will be many hours before Cesenatico’s beaches fill with glossy bodies rotating on sun loungers. For here is a town a bit like an Italian Blackpool – the same level of chintz, only with fewer arcades and more 14th century harbours, and with the proud boast of being Marco Pantani’s hometown. A fine place to start a coast-to-coast bike ride, then.

I join my fellow riders gathered along the harbour wall and we watch as the Earth’s inexorable spin turns the horizon from navy to orange. Seagulls have begun to circle overhead, perhaps attracted by an early fishing boat that’s putt-putting down the harbour canal. I take these last few moments to go back over my kit.

My top tube bag is stuffed with the three essential food groups for long-distance cycling: peanuts, bread and peanuts. Meanwhile my bar bag contains sun cream, energy bars and a back-up bottle of water. Europe is suffering a serious heatwave and today will not be the day I get peeled off the road like a dehydrated strawberry. In my jersey is the all-important brevet card, which is to be stamped at each of the three checkpoints.

‘Remember it’s a ride not a race!’ comes a shout from the front of our gathered pack. It’s Paolo, Chase the Sun’s organiser, espousing his event’s philosophy and likely some sage advice. A starter pistol cracks like the most exclaiming of marks, and we’re off.

The opening kilometres are Norfolk Broads-flat, the road snaking through farmland in an obliging manner for my legs, which haven’t been up this early in years. The pace is easy and it’s heartening to see the kilometres notch up until the foot of the first climb.

Nearly 40km down and it’s not even 7am. This is the longest day of the year (well, the longest Saturday) so there’s about 17 hours of daylight at my disposal, but I’ve done my sums and I reckon it will only take around 12.5 hours before I’m propping up a bar in Tirrenia. There’s 3,300m of climbing on offer, but over such a distance that’s hardly anything, right?

The first climb seems to validate the point. At 6km long and rising to just over 300m it’s more hill than mountain, but the second climb is a different beast. It’s certainly not a climb I’ve ever heard of, but 10km into Valico Tre Faggi I’m scratching my head as to why. It might only top out at a road-sog over 900m but it’s a mammoth 40km long and it starts near sea level.

As the road rises so the forests thin, the look-out spots become more frequent and Armco more guarded. Finally with treeline broached, the road flattens off and I dip around a bend to find a host of riders sitting around on plastic chairs. This is Bar Cavallino, checkpoint one and home to what Paolo described at the race – sorry, ride – briefing as having ‘the best focaccia in the region’.

I down tools and open the door to a dark room with a row of glass counters jampacked with the stuff. A great golden block of focaccia that could sink a battleship and be its own life raft is being sawn up on a huge wooden board alongside piles of Parma ham.

I exchange my food token for a dimpled slab, present my brevet card for its stamp and take up a chair in the sun. As predicted it’s hot, but there’s a nice breeze, I’m 90km in and it’s only 9.30am. Better get those glasses chilling, Tirrenia.

Red roofs and bridges

My exit from Bar Cavallino is nearly the end of my day. I overshoot a hairpin as a swerving driver screams ‘piano, piano!’ through her wound-down window. It’s totally my over-exuberant fault, so I take the descent as instructed: easy, easy.

I’ve long since crossed from Romagna into Tuscany, and while I wish I could say I could tell the difference, the landscape is basically the same – rolling wheat fields and green groves – although perhaps there are more vineyards. As if to prove this point, my computer chirrups the way like a guiding bird and I swing onto a steep single-lane track, which winds its way up into terraces of vines.

The air hangs like drying clothes, and while Tre Faggi was long, this unnamed climb is very much the steepest road so far. By the time it returns me to more rhythmic roads, I’m glad the undulations have stopped, even if there’s suddenly a lot more traffic.

But as the number of cars increases so does the availability of bike lanes, and this, plus the vacuum-suck of vehicles and imperceptible downhill, means I’m dragged quite effortlessly towards Florence. Terracotta rooftops soon come into view, then a colourful bridge I recognise from a long-ago holiday here, Ponte Vecchio.

I ride into the city through what feels like a chink in its walls, and instantly I realise this is no place for a person cycling across Italy. Mopeds buzz every which way, tourists amble dangerously and I am forced to unclip one foot and scoot. Through gaps and over bridges I catch glimpses of the roof of the Duomo, then comes a sign for the Uffizi.

It’s dazzling stuff, but so too is a gnawing feeling building inside. I become acutely aware my legs are willing me to stop, and it isn’t for the Renaissance paintings.

I crosscheck my bike computer with the route sticker on my stem and conclude this is well into the third climb. I’m exceedingly disheartened by the news. Since Florence my spirits have begun to wane, and the gnawing feeling has turned into a sinister clawing at the door. My legs have taken on a peculiar tightness, tense and empty like when you laugh so hard you can’t grip things properly.

Where before it was either too early in the day or I was too sheltered to feel it, the sun is now dangling mercilessly off some cosmic yardarm and the trees have been peeled back to leave just bleached roads. Despite my best bidon-filling efforts I have about three sips of water left, and with painfully slow calculations I work out it’s another 30 minutes of shade-free climbing before the second checkpoint and a tap. It is soul-crumpling to watch my altitude increase so slowly, but eventually through the heavy boughs of pine trees I spy the incongruous redness of Coca-Cola parasols.

I flop into my second plastic chair of the day and am quickly presented with a plate of pasta I don’t think I can eat. I close my eyes and down water until finally the slowly congealing ragu appears desirable.

Ten minutes later I can tell you that was the most delicious slowly congealing ragu I have ever eaten. I drink more water and wonder if parmesan contains electrolytes. I look at my computer and it appears I’ve been sat for so long it has turned off, but deep down I know I’m cured. The worst is over. One more climb, head for home.

Water burial

I’m not quite sure where I am but I’m sitting in a stream. I descended for a while. I stopped in a small village and bought a giant can of Coke and drank it on a bench next to a cat. I ate a brioche and so did the cat. I got lost. I sat back down in the same village square. The cat was gone. I would have wept but for the moisture loss. The temperature by this point was 37°C, so I found this stream and lay face down in it.

I have no idea where I am except there is still 60km to go and somewhere beyond here is another climb, and yet it is here that I want to die. I am OK with that. I don’t need to ride any further, or in fact ever again, and this stream is just the best. I don’t even mind the cluster of flies buzzing round my head. They can eat me and lay their children in my flesh when I’m gone.

Many more minutes pass until I can muster the resolve to ride again; crushingly it is only a few more minutes later that I become aware I am climbing again. It is hell.

The only time I’ve plumbed such depths was climbing at 3,330m, the air so thin that the energy just evaporated. And yet here I am, at just 300m, and the signs are the same. I feel like I’m running at full gas and yet my heart can’t get above 115bpm. My body feels so light I can’t tell if I’m sitting or standing, and yet in neither position can I exceed 9kmh.

In my defence the switchbacks are plentiful and not exactly shallow, but this is a strange fix I’m in. I can’t seem to drink enough water, but every sip makes me feel like I’ve ingested a waterbed. I’m either rippling or shaking, I can’t tell which.

Just get me home

I have drunk a coffee; I have lain on the grass. I am on the outskirts of Pisa when I realise I left my brevet book in the cafe at the top of the final climb; I am at the foot of the Leaning Tower of Pisa when I finally let go of caring.

All around me tourists are doing the mock ‘holding it up’ pose; down an alleyway well-dressed Italians are drinking spritzes in cocktail dresses and sport coats. Don’t ask me how I know they are Italian; in fact don’t ask me anything. I have to push my bike through this horribly happy crowd, so I swear volubly. Back on the road I take a wrong turn and I swear again, much too colourfully for a Catholic country.

When I finally reach the beaches of Tirrenia, I turn down the lane for the beach club that is supposed to be the finish, only to arrive on the sand at someone else’s club and someone else’s party. Too tired to care, I take off my shoes and wander through the throng, dragging my bike like an obstinate dog until I find the beach club I’m supposed to be in.

For the second time today I strip down to my bibshorts and jump in the water. It is dusk, I’ve been on the go for nearly 15 hours. I find a table on the terrace where I can see other riders arriving in similar states of disrepair and order a beer. This wasn’t quite the triumphant end I had in mind, but at least I’m not being recovered from that stream.

The chase is on

Buckle up, you’re in for a long ride

What: Chase the Sun ItaliaWhere: Cesenatico to Tirrenia, ItalyNext one: 24th June 2023How far: 275kmPrice: Entry from €148 (£130); packages including hotels and transfers from €699 (£612)More info: www.chasethesun.org

The rider’s ride

Cinelli Superstar Disc, £3,299, chickencyclekit.co.uk

If you’re wondering, that kink in the Cinelli Superstar’s top tube is to compensate for the extra forces generated when pedalling or braking hard, such that the head tube angle doesn’t warp, which thereby maintains continuity in handling. Does it work? I dunno, as at no point on this ride did I generate enough speed – I either didn’t need to or I was so knackered I couldn’t.

What I did manage to do was ascertain that the Superstar is a fine all-rounder, comfortable and easy going with a lively if not spritely feel. This is hardly a surprise as this build nudges 8.5kg and the geometry is fairly cruisy, with a wheelbase of nearly a metre and 387mm reach (size medium), but this just plays to the Superstar’s favour (and therefore mine) for such a long day in the saddle riding from one side of Italy to the other.

All in all the Superstar is a classy, composed act, plus I’ve always had a soft spot for white bikes. Especially when they match my Wizard Works luggage so well.

How we did it

Travel

Given that you start on one side of Italy and finish on the other, you’ll need two different flights. The closest airports are Bologna (1hr to the start in Cesenatico) and Pisa (20min from the finish in Tirrenia). Chase the Sun’s organisers can help with transfers and will gladly transport your luggage to the finish.

Accommodation

There are loads of hotels to choose from in both the start and finish towns, but the Hotel Miramere and Hotel New Bristol in Cesenatico are geared up for the ride’s 4am kick-off, and are mere metres from the start. In Tirrenia we stayed at the Continental Hotel, also very close to the end of the ride.

Thanks

It has been a long time since we’ve met someone who loves cycling as much as Paolo Tagliacarne. Together with his self-styled Turbolento crew (an Italian pun along the lines of ‘fast-slow’), Paolo – who is well into retirement age – puts on Chase the Sun as a passion project. ‘It makes no money, it’s just because we love it,’ he says proudly. He’s the reason we got an invite, and he couldn’t have been kinder or more hospitable over our stay. Thanks Paolo!

• This article originally appeared in issue 138 of Cyclist magazine. Click here to subscribe