Note to self: when finally giving in to the gravel revolution, it’s perhaps best not to go straight in at the deep end. Barely has the sun nudged above the horizon and I find my back wheel spinning wildly on the loose surface as I struggle up the steepening gradient.

I’m on the rocky road to Monte Sante Marie, a key section of sterrato – dirt road – that features in the spring Classic many believe has become cycling’s sixth Monument: Strade Bianche. It’s here where Tadej Pogačar struck out 50km from the finish to win last year’s edition, and it’s here where I’m already starting to think I’ve bitten off more than I can chew.

It has only been a matter of minutes since I rolled out of nearby Asciano, accompanied by my ride partner, Jacek Berruti – son of the late face of the L’Eroica gran fondo, Luciano Berruti. A short spin barely warmed up the legs before the road forked at a cemetery and tarmac gave way to gravel. We passed the milestone bearing the name of Fabian Cancellara, the record three-time winner of Strade Bianche, and now we’re following the ridge line through trees and above the low-hanging mist shrouding the valley.

At this early point in the day, with just the distant rumble of an unseen tractor following in our wake, it’s breathtakingly beautiful. Visibly so, for it’s still crisp enough to see every exhalation against the cobalt blue sky. My eye is drawn to the luminous glow of the first new growth of grass upon the corduroy indentations of the freshly ploughed fields.

This is the Crete Senese, the region of Tuscany known as ‘the clays of Siena’ where the harsh mattaione soil is renowned for its distinct grey colour and bleak lunar appearance. Flanked by the great wine areas of Chianti and Montalcino, the oak-heavy terroir is blessed by white truffles, while its grasses are grazed by sheep responsible for the local pecorino cheese.

For cyclists, though, the real draw is the network of white gravel roads that criss-cross the region, and which give their name to the one-day race: strade bianche.

Siena new light

As a dedicated road rider, this is my first real taste of unpaved roads, and so I’ve come suitably well-armed with a modern Cervélo gravel bike adorned with wide tyres and a 1x groupset. Jacek, meanwhile, sports an ancient-looking Gios bike and kit of the kind that is mandatory at the vintage Eroica event that takes place on these roads each year, and with which he is intimately intertwined.

He may look the part, but I don’t envy his narrow tyres and minimal gearing, even if it is the bike upon which Belgian Alfons De Wolf apparently won Milan-San Remo in 1981.

Any teething troubles I have on this rolling 11.5km section of gravel are soothed by the calm and bucolic artistry of our surroundings. Lines of cypress trees point skyward, flanking the tracks that connect isolated farms, wineries and agriturismi of the kind we stayed in last night – where a mural of Gino Bartali adorned the bike workshop wall, and our slow-cooked beef stew was served by a young semi-pro who recently raced against Vincenzo Nibali.

A lone deer crosses our path as we reach the top of a climb. We stop beside a rainwater pond, or fontoni, to admire the view from its lush green apron, including ravines intricately chiselled into the hills by Mother Nature’s tears. The imperious outline of Siena looms in the distance, and it’s a topographical marker as good as any compass.

The city is the start and finish point of the pro race, but for us it comes at around the 40km mark of our route. We could potentially avoid it altogether, but it would be remiss not to attempt the ramp where Mathieu van der Poel put down 1,362 watts on his way to victory in 2021.

My effort on the flagstones of the Via Santa Caterina is around 1,000 watts less convincing and all I have to show for it is a grazed elbow – the result of swerving to avoid the enthusiastic encouragement of an old man with a walking stick. As the road ahead is pedestrianised, we enter the iconic Piazza del Campo on foot before settling in for a coffee in the shade of the resplendent Torre del Mangia.

We’re soon back on the white stuff, heading along a section that Jacek knows well from the 23 editions of L’Eroica that he has ridden. I follow his wheel as he picks the middle line where the surface has been compacted by overlapping tyres tracks.

The few vehicles we pass are a reminder that these are functioning roads, still open to traffic and not just our playground. The dust thrown up provides a small taster of just how hard it must be to ride amid the race convoy.

It’s a huge workout to follow Jacek – both physically and mentally – and I greet the return of smooth, freshly laid tarmac with open arms. Before long we’re on an exposed downhill that allows us to build up a decent lick before joining the next gravel section at La Piana at full tilt.

It reminds me of the downhill approach to the Arenberg Forest in Paris-Roubaix and it’s mind-blowing to think that the peloton may hit the gravel at speeds in excess of 80kmh.

‘It’s who blinks first,’ says Jacek. ‘You have to forget the fear, turn off your brain and let your bike go. It’s a mixture of willpower, bravery and craziness.’ He tells me to lead the way, and I bury myself in domestique mode in a bid to impress my mentor. Only when I turn around near the end of the sector do I realise I may have overdone it; I’m on my own, my 38mm wheels clearly better suited to the loose and coarse gravel.

I’m left to contemplate a field of grazing horses, wondering if any of these thoroughbreds have taken part in another race that plays out in Siena’s Campo – Il Palio, the bareback horse race fought between the city’s 17 contrada, or wards.

Once Jacek rejoins me, he admits that he struggled to match my pace without taking too many risks on his vintage bike. ‘It’s much harder on a road bike,’ he says. ‘You don’t have as much control as on a bike like yours.’

We glide onwards towards Buonconvento.

Stealing some beauty

We shelter from the heat of the day over a simple lunch of panini and gelati in the town square before I head off on a loop towards Montalcino, leaving Jacek for a couple of hours to finalise a house purchase he’s in the middle of. I’ve ridden up to the hilltop town before on a road bike, wholly oblivious to the intricate web of dirt tracks carving through the surrounding vineyards.

Here grows the Sangiovese grape responsible for the world-famous Brunello di Montalcino, a bottle of which we enjoyed at last night’s dinner (it went down a wonder with a bowl of ribollita – Tuscan bread soup). I’m soon enjoying the splendid isolation of the Torrenieri section of gravel that runs parallel to the stretch responsible for Julian Alaphilippe’s acrobatic flight over the handlebars at the 2022 race.

A sweeping curve across a lush plain brings a smile to my face as I pass a handful of ramblers on the Via Francigena pilgrimage trail that briefly shares the same route. Rather ominously, a dead badger heralds the next section at Pieve a Salti, where Alaphilippe dug deep in his rainbow jersey to bridge back after his fall.

I stop to appreciate, atop a hill overlooking the road, an elegant holm oak of the kind under which Liv Tyler’s character loses her virginity in the film Stealing Beauty, shot nearby in Chianti. Apparently the local farmer charges up to €500 per hour renting the spot out as a picnic destination to romantics or rich influencers looking for some Instagrammification.

Suddenly I hit a series of steep switchbacks made all the more treacherous by deep ruts formed by drain water, but by now I’m starting to get the hang of this gravel lark, and I make it up with only minimal skidding and swearing.

Homeward bound

When I meet up with Jacek again for the last leg we head north on tarmac and take turns to pull, me tired from my extra exertions, him still warming up after time on the sidelines. After a pleasantly flat sliproad along the Arbia river, we join the final section of gravel at San Martino in Grania. It’s an undulating 9.5km slog that Strade Bianche awards a three-star difficulty.

After 100-plus kilometres in unexpectedly hot conditions, I find its series of punchy climbs arduous going. If it’s sometimes difficult to get a sense of how hilly Strade Bianche is by watching it on TV, then the same cannot be said when experiencing it, half-baked, in the saddle.

With the track going up and down, left and right, finding any rhythm is impossible. ‘How are you feeling?’ Jacek asks. ‘I haven’t got the legs,’ I reply. ‘But do you have the mind? That’s just as important a weapon.’

My mind is currently disengaging itself from my body by focussing on the golden sheen of the fields basking in the late afternoon sun. Siena has returned to the horizon, the black and white stripes of its duomo now in the shade. Behind us, clouds are gathering over the extinct volcano of Monte Amiata, and mainland Italy’s loftiest lava dome has taken on the aspect of Mount Doom.

By now even the flat and downhill sections offer little reprieve as the surface is so corrugated it shakes every bone in my body. For me it’s just about getting to the end, and I have newfound respect for anyone who races on roads like these.

Jacek reads my mind, for as we approach the top he says, ‘Every rider in the peloton is a hero in some way. Even the guy who finishes last, because he fought against the dust, the downhills, the punctures, the loss of balance. Strade Bianche is so different from a road race – it’s an experience.’

Before our final descent to Asciano, we savour the sunset from a ridge flanked by cypress-lined driveways. Jacek tells me how L’Eroica, which made his moustachioed father an icon, was born in 1997 by a desire to protect the strade bianche.

‘To me, Strade Bianche is not the sixth Monument, but maybe before the sixth,’ he says with delicious provocation. ‘It’s already better than Il Lombardia, perhaps Liège. The race may not have a history, but the roads do. It has become one of the greatest in the world because of the landscape and these roads. Ask a rider if they’d prefer to win Strade Bianche or Lombardia – we know the answer. Unless you’re Tadej Pogačar. He’d say both.’

These white roads that have become a symbol of Tuscany and a highlight of the WorldTour calendar were once threatened by modernisation and at one point faced extinction – like a rare animal. But the turnaround has been so huge that local councils are now even removing tarmac in places and returning the highways to their ‘natural’ state.

Given there are 1,600km of gravel roads in the Siena province alone, it’s a small wonder anyone bothers to ride anywhere else in these parts. One day alone has done enough to convert this entrenched roadie, and I’ll now watch with added insider knowledge when Pogačar defends his Strade Bianche crown this spring.

The rider’s ride

Cervélo Áspero Apex, £3,299

For card-carrying roadies such as myself, the Áspero makes the transition from road to gravel easy. This is a gravel bike that unashamedly feels like a road bike, made for riding fast rather than long-distance touring or tackling extreme off-road. There are no mounts for mudguards or racks, and its stiffness and spritely handling suggest a bike aimed at racing.

That’s not to say it’s uncomfortable – the 38mm tyres help to smooth out the bumps – but the more corrugated sections of gravel I hit were felt right through to my bones. The payoff was that the Áspero made light work of Tuscany’s short, steep climbs. And what’s not to like about the classy duotone ‘purple sunset’ paintjob?

Sixth Monument: The rise and rise of Strade Bianche

In 1997 the Eroica Strade Bianche gran fondo was established to celebrate a heroic bygone era when bike races were ridden on dirt or unpaved roads. A decade later a professional bike race was spun off the event. Initially called Monte Paschi Eroica (after the oldest bank in Italy) and held in early October, the first edition in 2007 was won by the Russian Alexandr Kolobnev.

In 2008 the race was moved to early March to become part of the spring Classics calendar, and that year marked the first of Fabian Cancellara’s record three wins. The organisers changed the name to Strade Bianche-Eroica Toscana in 2009 and then to just Strade Bianche in 2010. Since 2016 the race has started and finished in Siena.

Despite being a relatively new race, Strade Bianche has fast become a fan favourite. The Tuscan landscapes, the white gravel roads – arguably as challenging as the cobblestones of Flanders – and the iconic finish in the Piazza del Campo after the brutal ramped climb up Via Santa Caterina give the race its unique flavour.

Part of the WorldTour since 2017, it is seen by many as on a par with cycling’s five established Monuments despite being, at 184km, more than 100km shorter than Milan-San Remo. This quibble aside, the calibre of its recent champions – Julian Alaphilippe, Wout van Aert, Mathieu van der Poel, Tadej Pogačar, Anna van der Breggen, Annemiek van Vleuten, Chantal van den Broek-Blaak and Lotte Kopecky – suggests the riders certainly hold Strade Bianche in high esteem.

How we did it

Travel

The nearest airports to Siena are Florence or Pisa. Rome or Bologna are also options but require a longer transfer to the heart of Tuscany. Cyclist flew with British Airways from London Heathrow to Pisa for £200 return. We then took a train to Montevarchi Terranuovo (changing at Florence) for €18 one way.

Accommodation

Cyclist stayed at Il Molinello, a charming, family-run, bike-friendly agriturismo near Asciano in the heart of the Crete Senesi. Owner Alessandro Draghi is a part-time biology teacher, sommelier and vintage bike collector who has ridden numerous editions of L’Eroica and whose son, Guido, is a 21-year-old semi-pro cyclist.

Rooms start at €80 (£70) per night (or €420 per week) with prices higher during peak season. The fine restaurant specialises in local dishes that follow the admirable (and admirably delicious) slow food philosophy. Visit molinello.com for more details.

Thanks

This trip could not have happened without the intricate planning and patient support of Guido Gazzaniga, a Swiss army knife of practicality. As driver and tour guide, Guido pulled all the organisational strings – including, most crucially, the best gelateria recommendations. He will be leading a special Tuscany Gravel Explorer tour with Ride & Seek this May. Many thanks to Jacek Berruti for sticking around after L’Eroica, joining us on the ride and sharing his knowledge and passion.

Grazie mille also to Alessandro Draghi at the wonderful Il Molinello for hosting Cyclist, for the epic dinner, and for sharing so many stories of the path less paved. Final thanks to Tuscany Bicycle in Gaiole in Chianti for lending us a bike for the day (tuscanybicycle.com).

Tags: Best Bike RidesGravel