On the Trail.
At some point in the winter of 2024 Max suggested that we sign up for the Tuscany Trail and, in a classic display of why women tend to live longer than men, Ariel and I agreed on the spot. It was only in early May 2025, with departure day a few days’ away, that the implications of what we’d done hit us. Four-hundred and thirty kilometres, more than six thousand metres of height gain, all by bicycle, over four days.
But by that time there was no turning back.
Day 1
Campiglia Marittima – Giuncarico (106km, 813m height gain).
It wasn’t until the late afternoon of D-minus 1 that our band of amateur bikepackers convened in the bourgeois confines of the glamping site which doubled as our basecamp. We all had our roles: Max was the bike mechanic, Ariel the athlete, and I was the organiser. To say that our experience of multi-day rides was limited would’ve been charitable; nonetheless, on that fresh morning in May we all lined up and joined the hundreds of fellow cyclists that were already out there, tackling the self-professed “world’s leading bikepacking event”.
Spirits were high as we started the first gravel section outside the medieval borgo of Campiglia in a joyful jamboree of cyclists of sexes, ages, nationalities and bike inclinations. There was none of the competitive tension of other events; everyone was there to complete the ride and have a good time, not to win a medal. Chatter in a dozen of languages mixed with the whirrs of freehubs and the tempo, buoyed by the collective optimism, was high. It couldn’t last, and indeed it didn’t.
The road dove into a forest of fragrant maritime pines, aiming straight for the blue Tyrrhenian Sea, disintegrating as it did. At its worst it was a rutted, smooth and muddy slip- ‘n’-slide. Ariel and Max both dabbled in downhill MTB and made quick work of the most technical sections. I, burdened by tyres not designed for mud and a severe lack of skill, inched forwards at a snail’s pace.
It was but a moment; back as a trio, we passed through the seaside towns of Follonica and Castiglione della Pescaia as they were getting ready for the summer season. Beach umbrellas and loungers were already lined up on the foreshore, and the few early visitors looked on with curiosity as muddy cyclists emerged, bags and panniers hanging from their frames, on the lookout for the best places to eat.
Eating and drinking are the main preoccupations of the bikepacker. Having failed to extol the virtues of Lidl pizzas, I tried at least to convince my comrades of the health benefits of Radler beer. I could see that they doubted my claim that a mixture of pomegranate juice and beer could sort out cramps, nourish the body, soothe the soul and give you an extra 20 Watts on climbs, but I was sure that they’d be convinced as soon as we’d found some. Which turned out to be a problem, for no shop in Tuscany seemed to be selling that nectar. Only sub-par lemon Radler was available, and of the kind that tasted like dishwashing liquid.
Past Castiglione, the trail abandoned the sea and cut through the Maremma flatlands. This was a Tuscany that normally didn’t feature in the tourist brochures: flat, lush with cultivations and bisected by canals. We rode on, buoyed by a potent tailwind, and joined forces with a trio of Danish cyclists who, at first, seemed a bit closed off. Then one of them spotted what turned out to be the trip’s best icebreaker: the Bluetooth music speaker dangling from Max’s saddle bag. He asked our resident DJ to play something Italian and he obliged with, in his words, “some of our finest trash”. Out came a 1980s playlist that, for reason unknown to science, is incredibly popular with Uzbek truck drivers and now, Danes on bikes. If bars in Copenhagen start blasting Al Bano and Romina Power, it’s our fault.
Day 2
Giuncarico – Murlo (144km, 2,300m height gain).
The Tappone, or Queen Stage, of our very personal Grand Tour was today. The length, and constant up-and-downs, loomed large in our minds and it was with a sense of foreboding that we rode out of Giuncarico, turned left and pedalled straight into a headwind.
Cycling is a team sport. You might be alone on your bike but if you’re riding with someone then you’re in a squad, and we were no different. Masterfully directed by Max, we filed into a single line, rotating the man at the front, facing the wind, so that the other two could sit on the wheel of the person ahead and burn less energy. Our three-persons peloton worked in unison and, before we knew, thirty kilometres had elapsed, the headwind had gone, and it was time for what Ariel dubbed “our second breakfast, Hobbit-style”.
At some point the road rocketed skywards and the group splintered. Ariel, despite being troubled by knee pains, discovered his inner Marco Pantani and charged uphill like a man possessed. Max was hampered by a cassette more fit for flat riding and I found myself somewhat in the middle. Eventually, the gravel ramps gave way to the cobbled streets of another Castiglione – in Orcia, this time – and, as it happened, it was time for lunch.
Imagine a plague of locusts in Lycra, marauding Vikings riding bicycles, smelly barbarians on the hunt for carbohydrates: this was the scene that unfolded in every town, village and chicken coop along the route of the Tuscany Trail. Bikepackers, rendered ravenous by hours of riding, sat at every table, lined at every shop, even those that only sold motor oil. Castiglione d’Orcia, when we arrived, was already under siege. Men and women in bibs and clipless shoes were drinking beers, spritz and Cokes (sometimes all at the same time), ate bowls of pasta and lined the little convenience store where the stash of focaccia was rapidly dwindling. Then they’d move on, towards the enchanting hills of val d’Orcia, home of smooth white gravel roads, medieval abbeys, row of cypresses but, alas, no pomegranate Radler.
The gods of cycling smiled benignly upon us as the Queen stage ended with one last climb, this time on tarmac, towards Murlo. Swallows danced in the late afternoon air, the road was empty and then there was Murlo, sitting pretty on an outcrop, beaming with the promise of good food, rest and, yes, spritz for us too.
Day 3
Murlo-Volterra (108km, 1,864m height gain).
The breakfast hall of the hotel was, predictably, overrun with people in bibs. “Forty-six rooms, all taken, and only three aren’t cycling” commented the receptionist the day before.
“This is it, boys” announced Max as I slathered honey on a slice of bread. “A proper bastard of a route, today”.
“I thought the hard day was yesterday”, said Ariel with a tinge of worry. A true hero, he’d barely glanced at the .gpx track of the entire route before starting.
“The third day’s always the worst”, I philosophised in response, caught in a brief Yoda moment. “Besides, today’s the climb is all at the end”.
Suitably forewarned, we got back on the road. Despite the thousands of participants, it felt as if we’d been travelling with the same people throughout, and familiar faces started popping out along the course. Max’s speaker had become famous, as well as our habit of putting on music to help us on the climbs, so it was no surprise that he got a request for a funky song. If you were on the road to Siena, that day, and saw a bunch of cyclists grooving to Al Green’s I Feel Good, then you know the backstory.
Siena, when we got there, was in the throes of Palio preparations. As we passed through, three contrade were going to be drawn for their chance to compete, and the medieval streets of the city echoed with the sound of drums as supporters made their way towards City Hall. Later we got to Colle val d’Elsa and there the main square hosted, on one side, a carousel of Slovenian cyclists riding in circles around the fountain while, on the other, bikepackers sat at a café next to families celebrating their children’s First Communion. The dichotomy between the angelic figure cast by the kids in their pristine white robes and the cyclists covered in dust, their clothes encrusted with salt, was something worth of the Divine Comedy.
Our hotel in Volterra was quite a way from the official track, and I engineered a detour. As it often is the case this was a deceitfully simple task: a beautiful road could turn out to require fording at least a river, a scramble up a quasi-vertical slope, or a little bit of trespassing.
On the topic of trespassing, the beginning wasn’t very auspicious: a sign warned that the road we were intending to turn onto was private. “If they really wanted to keep us out there’d be a gate”, I said, spurring my comrades on. So we descended a gravel path that got increasingly steep and rockier. “I’m not riding back up if we can’t continue”, warned Max, before the detour yielded… gravel paradise.
The woods gave way to a wide, open valley with views stretching as far as the eyes dared going. In front of us was a long descent and a beautiful left-hand turn that then led to a ridgeline. It was late afternoon by then, and the angle of the sun gave everything – the green fields, the hills, the thickets of oaks, faraway villages – a golden hue as if Tuscany had been dipped in honey. We dove down the descent and then discovered an impossibly beautiful road: smooth gravel, painted curves, a racer’s dream.
Max sensed the moment and put some Depeche Mode on. It’d been years, maybe ten, since I’d heard Enjoy the Silence, and there I was, riding with my mates. In that moment words were very unnecessary indeed.
The hotel was a former convent located just outside the town of Volterra, right after the hospital. On my way there I considered just asking for a bed in a ward, any ward, of the clinic. Today’s climbs were all at the end, that we knew, but the last had been brutal. An average of 8% gradient for seven kilometres, with peaks of 17%. Drenched in sweat, legs the consistence of noodles, I managed to tiptoe past the ambulance parking lot and got to the hotel, looking for beer and a shower. The other two arrived soon afterwards and, after the briefest of debates, we elected to eat in and enjoy the earliest of early nights.
Day 4
Volterra – Campiglia Marittima (79km, 870m height gain).
Today was the day of one of the greatest comebacks in amateur cycling. We started unsure of whether we’d be finishing as a trio and we ended it… well, I’m getting ahead of myself.
Overnight, Ariel had been unwell; at breakfast, Max and I were thinking that, with all probability, he’d scratch out of the event. Had I been that sick, I reasoned, I would’ve been a mollusc. Instead, Ariel made an appearance at the buffet and announced his intention to try and ride. “Afterall it’s downhill now”. We didn’t have the heart to tell him about the climbs ahead.
So began Ariel’s ordeal. Both his knees were in agony. His stomach ached. Then back pain. For good measure, his cleats and pedals start having a falling out and his bike developed some mildly worrying creaking. The long descent from Volterra turned into a long slog upwards towards Montecatini, then some relentless saliscendi until Canneto, a hamlet featuring the usual mobbed bar and shop. Ariel had been, until then, munching Ibuprofen and Gaviscon. But, once he’d wolfed down a focaccia the size of a paving slab, things started to turn.
We got back on a road that was totally devoid of cars and simply idled downhill while listening to Bee Gees. Soothed by the therapeutic effects of the Gibb brothers, Ariel’s internal battery started to recharge. Max and I took turn leading the peloton, setting a steady 25km/h rhythm, under a strict “no attacks” mandate. Then, out of nowhere, a missile passed us by. It looked like Ariel and, once we’d accelerated to 35km/h to catch up, we found it was indeed him. He was back.
Our convoy of madmen forgot that we’d just broken the 400km barriers and started hammering. Max put on the speaker the worst possible spinning class compilation and, spurred by (or despite) it, we ate the miles, pulling others along as if we’d all been told that there were free beers at the arrival.
Then, something unexpected happened: a blue track appeared on my Garmin. This meant that we’d been there before, and we were retracing our steps. The loop had been closed, and our arrival point beckoned. Indeed that was the case: soon we saw the Carabinieri station, the roadside station, and the small car park of Campiglia Marittima. A little further along I spotted the turn for the glamping whence we’d departed, four years and two lifetimes ago.
There was whooping, there were high-fives, there were sweaty hugs. The relief of completing the challenge we’d unconsciously stepped in washed over us like a tide, and we rode it for a while, drinking beers and eating pizza together. Then, as our company parted, the slow realisation hit us all. Tomorrow we’d no longer be riding along the Trail, and the tiring but simple life we’d been growing used to wouldn’t come back. The next day Max messaged “I miss riding my bike, guys” and we all did.
