Choose Your Own Adventure: Milan-San Remo

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Do not read this article through from beginning to end! There are many different possible endings, and many different adventures you can have on the road from Milan to San Remo.

As you read along, you will be given a series of choices. What you decide will impact the rest of the race, and might lead you to glory … or defeat.

Will you take the win at the end of the day’s racing? Will you help your team to victory? Or will you be left wondering what could have been?

Only you are in control of your fate in the 2020 edition of Milan-San Remo. Good luck – and choose wisely.

Go to 1.


Day breaks in Milan, and the first monument of the season lies in wait. On the menu for the day ahead – 293 km of early-spring kilometres, down to the coast and to the famed finish in San Remo.

At the starting site, lines of sparkling team buses line the roadside. Inside them, the riders receive their orders from the team directors, pin their race numbers to their jerseys and have a last coffee before sign-in. You’re an opportunist – you’ve got a teammate for the sprint, but you’ve got a free role to look out for opportunities as they come. You sip an espresso, and try to imagine how your race will pan out.

Finally, it’s time. The peloton lines up at the start line, and the race announcer counts down.

Go to 2.


Until the race clears the city centre, everything’s pretty manic. You nervously scan ahead for the smoothest line through the cobblestones and the tram tracks. Around you, you hear the squeal of brakes, the nervous exhalations of riders avoiding collisions at the last second.

Pretty soon thereafter, the first attack of the day goes. In it: two riders from Bardiani-CFS-Faizane, a rider from Circus-Wanty Gobert, a rider from Alpecin-Fenix, two from Novo-Nordisk, a domestique each from CCC and Trek-Segafredo and a rouleur from Israel StartUp Nation.

What do you do? Do you jump on the move (6), or let it go (13)?


As the four chasers disappear up the road, you take a look around for your team leader. It takes a moment to spot him, but there he is, a couple of riders behind you. He’s looking a little worse for wear — he’s rocking back and forth in the saddle and seems to be struggling to hold his position. You’ve got a decision to make, and quickly — if you’re going to catch the four chasers you need to go right now.

Do you pause briefly and wait for your leader (46)? Or do you seize your own opportunity and set off alone (53)?


You tap away comfortably as the peloton snakes its way along the Mediterranean Coast. The breakaway has been caught and the race is now entering its next phase. The pace is surprisingly sedate up the first two ‘Capi’ but when the race reaches the Capo Berta, the intensity suddenly lifts. You’ve been instructed to keep an eye on Vincenzo Nibali in the closing kilometres, knowing he’s a dangerman. He’s been very relaxed until now, but as the pace ratchets up on the Capo Berta, you notice Nibali has started to work his way up through the field.

Before you know it, he’s more than 50 metres ahead of you, in a bunch that’s narrowed out as it passes roadside fans who have started to light flares. There’s still more than 40 km to go in the race and the peloton doesn’t seem to be splitting yet, but you know what Nibali is capable of.

What do you do? Do you sprint up the outside of the bunch, to get to Nibali as quickly as you can (38)? Or do you try to move up gently, picking your way through the bunch (48)?


To your great surprise, the reduced peloton of around 20 manages to catch the five leaders just as you turn off the descent. Alaphilippe and Nibali must be having an off day.

As the two groups come together, and everyone looks around to see who’s still there, there’s a careless touch of wheels near the front. Carnage ripples through the group and suddenly the group of 25 is down to just 10.

By pure chance, you’ve managed to stay upright. A quick glance at those around you suggests that your team leader has too. With just a couple kilometres remaining, your team has two out of 10 riders and a great shot at victory.

The question is, how are you going to play it? You’re feeling strong, and you rate yourself a good chance of victory if it comes to a sprint. Your team leader was looking terrible at the top of the Poggio and even now looks like he’s only just hanging on.

Do you ride for yourself (34)? Or do you keep riding for your leader (45)?


Almost instinctively, you spring forth from the front of the peloton, pushing through the frigid air to try to get on the back wheel of the group ahead of you.

For several minutes, you’re hovering in the no-man’s-land between the two groups on the road – the breakaway still moving away, and the peloton easing off. You can feel the effort starting to sting your legs.

Between ragged breaths, you look down at your power meter and wonder how much longer you can sustain this. Milan-San Remo’s such a brutally long race, and you’re burning a lot of energy early.

Do you give up and return to the peloton (41), or keep pushing to make the breakaway (20)?


You nestle safely on Alaphilippe’s wheel as the six of you wind up for the sprint to decide Milan-San Remo. You chose the right wheel — Alaphilippe manages to get the jump on the rest of the group and opens a handy lead. But you’re right there, tucked into his slipstream, waiting for the perfect moment.

With 100 metres to go, you know it’s time. You pull out of Alaphilippe’s slipstream and edge in front. You throw for the line with all your might.

You look across at Alaphilippe and he looks at you. It’s close. Super close. Neither of you is confident enough to throw your hands in the air.

It takes a couple minutes for the commissaires to review the finish line photo. And then the announcement comes over the loudspeaker. You’ve done it. You’ve won Milan-San Remo!



You descend the Poggio sedately then join up with a big group as it works through the final few kilometres into San Remo. You cross the line a few minutes behind the winner, in about 40th place.

As you reach your team soigneur you ask how your leader went. Ninth. Not too bad, but not the result you were after.

Perhaps you should have waited with them on the Cipressa? Or not worked so hard on the Poggio? Ah well, there’s always next year.



You take a deep breath, and try to block out the fear as you follow Nibali on the descent. He’s using every inch of the road, swinging from guardrail to apex on corners, off the brakes. It’s a masterclass.

You try to follow him through a tight hairpin, leaning your bike over, blocking out every instinct that is telling you to slow down.

Suddenly, your tyres hit a wet-patch on the road. You tense up as the bike slides out under you and your body goes skating across the road into the gutter. With a sickening thud, your arm hits a guardrail, and you scream out in agony.

As the race doctor’s car screeches to a halt next to you, you realise that your race is over.



It’s tempting to jump across to Bonifazio as he barrels off the Cipressa – not only does it look like fun, but if the move works, you know you can beat him in a sprint. But it’s too early — this move is destined to fail.

You bide your time in the bunch, descending as safely as you can while maintaining your position in the bunch.

Go to 40.


There’s no time to lose – Nibali’s gap is growing quickly, and you can see that he might ride away with the race if no one closes him down. You unleash a vicious acceleration to get back in contact with him. You’re burning more matches than you’d like at this stage of the race, but you realise that it’s a necessity.

The gap slowly closes, and Nibali glances back over his shoulder, sees you closing, and slows slightly to enable you to get onto his wheel.

Go to 18.


You pounce immediately, pushing your way out of the bunch and out into open road in pursuit of Nibali. There’s still a little bit of climbing to go and you’re confident you can reach him.

You dig as deep as you possibly can, knowing that getting away with Nibali could well be the winning move. Sure enough, with about a kilometre to go, you make contact with the Italian. But unbeknownst to you, you’ve got company.

Peter Sagan, Greg van Avermaet and Caleb Ewan have all been able to follow you across to the front. There are five of you with a handy little gap over the rest of the field.

And then Nibali cracks. It’s a surprise to all of you, but suddenly the Italian can’t hold the wheel and then, in a matter of moments he’s gone. It’s just you, Sagan, van Avermaet and Ewan left as you begin the descent off the Poggio.

Go to 26.


As you pass through the village of Pavia, 24 km into the race, you finally lose sight of the breakaway around a corner lined by cheering fans. They can suffer off the front and hog the screen-time for their sponsors – you can’t imagine they’ll still be there in five hours time, when it counts.

The kilometres tick steadily down, interspersed with the small towns you pass through on the way – little glimpses of rural Italian life.

You sit in a long string of riders behind the powerhouses of the peloton, led by Adam Hansen (Lotto-Soudal) who sits on the front, keeping the deficit in check.

Go to 14.


The calm conditions of the morning have become less stable. As the race approaches the first feedzone, just before the climb of the Passo del Turchino, you notice dark clouds forming over the back of the hills. It’s getting colder, too.

As the main field rides up the Passo del Turchino, it starts to drizzle. Or that’s what you think at first, anyway. But then the drift of the droplets through the air seems to slow, and you realise that it’s sleet dancing through the air. Despite the pace at which the peloton moves up the climb, you can feel the temperature continuing to drop.

Ahead lies an almost 10 km descent. Decision time.

Do you try to grab a newspaper at the top of the climb to to stuff down your gilet at the top of the climb (36), or drop back to the team car for a jacket and gloves (51)?


You push your way onto Sagan’s wheel as the finish line comes into view. You’re glued to the Slovakian’s wheel, knowing that there’s few better riders in the world in a sprint after such a long, hard day.

Sagan kicks early — too early — as Ewan and van Avermaet look set to surge past. It’s now or never. You jump out of Sagan’s slipstream, and edge ahead of him, but it’s to no avail — Ewan and van Avermaet have sailed past with mere metres to spare. Ewan takes the win, and you cross the line third. A podium at Milan-San Remo — that’ll be one to remember. But could it have been a victory?



You desperately look around for someone to help you close the chase down, and heave a sigh of relief when a small group forms and starts working to reduce Nibali’s advantage – it’s you, Tim Wellens, and Gianni Moscon.

As you climb on Moscon’s wheel, however, you realise that his intentions may not be totally pure – he’s surging on and off, trying to disrupt your rhythm, yelling about how you cut him off earlier. Suddenly he brake-checks, and you in turn need to slam on your brakes to stop in time to avoid running into the back of his bike.

Your body is weighted all wrong; you go flying over the handlebars and land on your arm, feel your collarbone crack, and lie in agony on the side of the road. As you wait for medical assistance, you see the race whoosh pass you, and realise that you won’t be making it to San Remo this year.



Apart from a few riders who are having a bad day, the bunch stays together over the Capo Berta. As you descend back down to the coast, you know you’ll have to be hypervigilant from now on. The Cipressa is just around the corner.

The pace is on as the bunch flies towards the penultimate climb. You’re well positioned — close to the front, but not too close. As the peloton hits the bottom of the Cipressa, you’re primed and ready to follow the dangerous moves. But they never really come.

A few riders try to get away but they can’t make anything stick — the pace in the bunch is too high. You’re battling hard to stay up front, but this is well within your capabilities.

A thinned-out bunch crests the Cipressa and there’s a collective sigh of relief as riders take the opportunity to take a brief moment of respite as the descent begins. In that momentary lull, as the bunch starts to snake its way back towards the Mediterranean, Niccolo Bonifazio bursts clear. Before you know it he’s 10 metres clear of the bunch, now 15, now 20. He’s descending at breakneck speed, clearly taking great risks to try and open up a lead. What do you do?

Do you follow him (23), or do you sit back in the bunch and wait (10)?


The two of you crest the Capo Berta, Nibali leading and you glued to his wheel. The Italian puts in a powerful surge over the top, and it’s clear that he’s hoping to use the descent and his renowned bike-handling skills to increase his advantage.

Nibali was great on the climb, but today on the descent he’s on another planet, taking unbelievable risks to open his gap on the peloton.

You’re not the most confident descender, but realise that this is your chance to win a Monument.

Do you ride at your own pace and try to reel Nibali back in later (22) or take the risk of trying to stay with him on the descent (9)?


Nibali rounds a corner ahead of the bunch and with that, he’s out of sight. There’s a nervous energy in the peloton as if, as one, the rest of the field has realised the danger. Julian Alaphilippe launches clear of the bunch, and he’s followed swiftly by Matteo Trentin, Wout Van Aert and Philippe Gilbert. This is the move — you can feel it.

You try to force your way out of the peloton but, at exactly the wrong moment, you’ve found yourself boxed in. After a few seconds you finally get clear road ahead of you, but by that stage the four chasers have already opened up a sizeable gap.

What do you do in this moment? Take a second to look around for your team leader (3)? Or just drill the pace and try to get across, assuming that your leader is right behind you as planned (35)?


Finally, you make contact, and settle into the rhythm of rolling turns. It’s been a brutal chase but you hope that you’re able to regain some strength for later in the race when it will matter.

It’s still a while to go until the first feedzone of the race, and you reach for an energy bar in your pocket. As your glove-covered fingers try to open it, you hit a bump and it falls to the ground.

You look over your shoulder to watch it tumble into the grass on the roadside. Swearing under your breath, you fix your eyes back on the rider ahead. He flicks his elbow, and you pull through for a turn.

Go to 21.


After a testing first couple of hours of racing, you’re starting to get hungry. The peloton’s closing the break down and the cars have been pulled out of the gap. You’re out of food, the manic pace of the breakaway keeps lifting, and you’re afraid of getting dropped.

You ask a fellow rider for a gel to tide you over. He agrees, on the condition that you promise assistance later in the race if the breakaway survives.

What do you do in this moment? Do you accept his offer – and the moral compromise (28)? Or do you decide to wait a little longer before eating (30)?


After a sphincter-puckering left-hander, where you almost clip the apex, you decide to ease off a little – there’s still the Cipressa and the Poggio to go, and you reckon that even Nibali will struggle to hold off a highly-motivated peloton by himself.

Your gamble pays off. By the Cipressa, Nibali’s getting brought back, a dangling figure in Trek-Segafredo kit that gets closer with each surge of the chasing pack.

Pretty soon, it’s all back together: Nibali’s breakaway is over, and he sits in the first few riders of a strong reduced peloton.

Go to 40.


Before you even realise what you’re doing, you’re sprinting out of the bunch on the descent off the Cipressa. This is a technical descent at the best of times and you’re making it even harder for yourself with this frenzied chase. But the adrenaline is pumping and you’re committed now — you have to catch Bonifazio.

You’re cornering faster than you ever have. You’re railing corners with mere millimetres of room to spare, coming much closer to concrete walls than you would like. But the tyres hold and you’re up to the task.

You open a gap on the peloton and as the road flattens off down by the coast, you can see Bonifazio up ahead. You glance behind and see that the peloton has backed off a little — they don’t think you two can survive so they’re giving you space.

It takes a mammoth effort but you bridge across to Bonifazio just as the Poggio looms up ahead of you. You start the climb together, Bonifazio leading you up at a crazy speed. You’re hanging on but only just. And then he flicks his elbow asking you to come around. You’ve got a solid turn in you, but do you want to? Are you better off saving your matches for later?

If you do a turn, head to 42. If you sit on, go to 29.


It’s all or nothing. As hesitation sets in, you catch a glimpse of Nibali around a corner and decide it’s time to go. You jump off the front of the lead group, and a gap starts to open up. Your director sportif is yelling in your ear to ride for your faster-finishing teammate, but you’ve got your eyes on the win for yourself.

You finally latch onto a tiring Nibali with 500m to go, but he’s got nothing left to give – and besides, he doesn’t want to tow you to the line. He sits up, and the two of you are swamped. You hear the crowd roar and watch numbly as the chasing pack passes you. Your teammate finishes fourth, and you cross the line in fifth.

Your team director is not pleased, and lets you know all about it at the team bus.



You gratefully reach a hand out onto the window-sill as the team car accelerates, propelling you effortlessly back onto the peloton. Easy-peasy! And besides, doesn’t everybody take a sticky bottle from time to time? It’s barely cheating if everybody’s doing it, right?

Unbeknownst to you and your team director, however, a TV helicopter has been hovering overhead filming your indiscretion and transmitting it to the world.

A few minutes later, the race radio announces your disqualification. Furious and ashamed, you pull over, remove your race numbers and climb into the team car, your race over.



You, Sagan, van Avermaet and Ewan barrel down the Poggio and down towards San Remo. On the flat approach to town you all work well together, knowing that your best chance of victory is to hold off the bunch that’s hunting you down.

But inside the final kilometre, a quick look behind suggests that they’re not going to catch you. The winner is going to come from this leading quartet.

It’s three hundred metres to go and you’re trying to work out whose wheel to follow. You know that you’ve got your work cut out — your sprint is good but not as good as these three.

So how do you play it? Do you follow Ewan’s wheel (44)? Or Sagan’s (15)?


You latch onto Van Aert’s wheel as you fly into the final few hundred metres. The Belgian launches his sprint a little late, caught on the hop by an impressive jump from Alaphilippe.

You’re caught behind, and you’re slightly boxed in, with Van Aert ahead of you, Trentin and Gilbert to your left. Your only chance of getting out is to go right, through the narrow gap between Van Aert and the barriers.

As you surge up the right, Van Aert comes across ever so slightly, but it’s just enough for everything to fall apart. You stop pedalling for a microsecond, and as you do, your shoe clips the foot of a barrier. In an instant you’re tumbling to the ground at more than 60 kph.

Your Milan-San Remo is over, just 100 metres from the line.



Begrudgingly you grab the gel from your breakaway companion, slurp it down, and pull through for a turn.

5 km later, the route turns into a crosswind, and the breakaway is buffeted by gusty winds. The advantage starts to plummet downwards, as the peloton moves in for the catch. Soon after, it’s all over for your breakaway attempt. You soft-pedal down the side of the peloton, until you find the friendly face of a teammate. He’s just on his way back from the team car, and passes you a couple of gels and bars, which you wolf down. You’re starting to feel human again.

Go to 4.


Bonifazio is flicking his elbow like an absolute fiend. And now he’s turning around and yelling at you, imploring you to help with the pacemaking. You don’t understand Italian but it’s clear from his tone that he’s not happy.

But you hold firm — you’re not convinced this move is going to stick, and you don’t want to expend any more energy than you need to until you know it’s going to be worthwhile.

And then your DS is screaming in your ear – telling you that Bonifazio is going to get caught, that you need to stop working immediately, that you need to come back and help your leader. Somewhat reluctantly you ease off the pedals and watch as Bonifazio edges away on his own.

It takes 20 seconds or so and then the peloton is upon you. You’re back up to speed by the time the front of the bunch reaches your back wheel and you slot in next to your team leader. “What were you thinking?!” he yells.

Go to 33.


You battle on, but you’re delirious with hunger and when the breakaway puts in a surge over a small rise, you lose contact.

Your legs seem to have turned into useless meat-sticks and you’re seeing double. You curse your inexperience for getting caught out like this in one of your team’s major targets, and from behind you hear the whoosh of the peloton closing in …

They fly past you in a flurry of colour, and soon you’re off the back among the team cars. You glance over your shoulder, weakly raise a hand for your team car, and pull over. As the mechanic lifts your bike onto the roof, you weep bitterly.

Your race is over; a couple of hours later, your team leader is isolated, gets dropped on the Cipressa, and finishes an unspectacular 24th.



Nibali’s move feels too early to you. There’s enough of the climb left, and a big enough chasing group, that you’re confident he’ll get caught. You hold firm in the second row in the peloton as Nibali slowly inches further and further away.

You hope you made the right call …

Go to 19.


You wait for Alaphilippe, or Gilbert, or Trentin, or Van Aert to pull through and take a turn, but everyone’s watching each other and Nibali’s not slowing down. It’s just like 2018 all over again.

As you wind up to lead out your teammate for the sprint, you watch Nibali sit up, salute the crowd and cross the line. You’ve conserved enough energy for a great lead out, and your team leader is next across the line, both mere seconds and an eternity behind Nibali. It’s a successful outing for the team, but you have to wonder what could have been.



You’re questioning the wisdom of your decision to chase Bonifazio. But you’ve still got a chance to redeem yourself here.

You reach the top of the Poggio in a group of around 30 riders. Your team leader is there and from a quick look around the bunch, you assess that he’s probably the best sprinter of the lot. This is your chance.

Bonifazio is only about 15 seconds ahead as your chase group reaches the final few kilometres into San Remo. You know what you have to do.

You go to the front of the bunch and ride as hard as you possibly can. You’re paying for your earlier effort, but you’re still making inroads. With some assistance from other teams you drag Bonifazio back inside the final kilometre. And with that, your job is done. You drift back as your team leader readies himself for the final sprint.

As the race disappears up the road ahead of you, you watch carefully to see what happens. Off in the distance you see your teammate throw his arms in the air. Your team has just won Milan-San Remo!



This is your chance. You’ve never had such a good opportunity to win a Monument. You know you’re supposed to be riding for your team leader but he’s not looking the best and besides, it doesn’t matter who wins so long as the team wins, right?

There’s 10 of you left on the Via Roma as you wind up towards the final sprint. You search out the best wheel you can for the sprint, leaving your teammate to do the same.

As everyone jumps out of the saddle and kicks for the line, you realise that you and your team leader are sprinting against one another, both believing that the other doesn’t have a chance at victory. You cross the line in third and fourth, much to the amusement of the watching fans. Your DS is far less impressed.



There’s no time to lose: Nibali’s out of sight, and there’s daylight opening between you and the group comprising Alaphilippe, Trentin, van Aert and Gilbert. You need to get onto this move, and now.

Lactic acid burns your legs as you push yourself to the limit to get into Gilbert’s slipstream. From behind, you hear your team-mate yelling to let you know that he’s on your wheel – “go-go-go!” – and you grit your teeth as you tow him across. After what feels like an eternity, the two of you make contact.

The group works together well, and you settle into rolling turns for a couple of kilometres, but Nibali’s still dangling off the front. As you pass the 3 km to go marker, the impetus seems to drop in the chase group, just slightly, and you realise that everyone’s hedging their bets for the sprint for second.

Decision time: do you put in a last-ditch solo bid for glory (24), get on the front to close it down for your teammate (39), or wait for someone else to do the hard work (32)?


You’ve decided to avoid the hassle of going back to the car and potentially losing contact with the peloton, but it’s a gamble – you now have to hope that there’s a soigneur or spectator at the top of the climb that you can grab something from to keep off the chill.

As you crest the Passo del Turchino – the high point of Milan-San Remo – you scan the roadsides for a soigneur or spectator holding out a newspaper that you can stuff down your gilet.

Decision time: do you drift to the barriers lining the top of the climb to grab one there (47), or hope that there’s one you can grab on the roadside just over the crest (50)?


You decide to take the moral high-ground, and swing away from the car, punching out an acceleration to weave your way back through the cars and motorbikes to the back of the peloton. That was close – a moment of lapsed concentration and you were almost off the back and out of the race.

Nonetheless, you’re grateful for the extra coverage – it’s extremely cold as you descend toward the Mediterranean coast.

Go to 4.


You berate yourself for letting Nibali catch you off guard like that. You move to the edge of the peloton and jump out of the saddle, forcing your way up the outside to try and catch the Italian.

You’re getting close to roadside fans and the smoke from the flares they’ve just lit is getting into your eyes. But your DS was clear at the start of the day — watch Nibali like a hawk. You know you’ll cop an earful if you let him get away here.

You’re making progress on Nibali but as you round a tight corner the smoke haze thickens. You can barely see. And then, suddenly, you’re on the ground. You’ve hit a spectator. Or maybe they stepped out into your path. It’s not clear. Either way it doesn’t matter. Your race is over.



Your team director yells into your earpiece to get on the front and close down the gap. The orders are clear – work for your teammate, do everything you can to get him over the line first.

He’s locked on your back wheel. Pushing as big a gear as you can, you start to close the gap on a tiring Nibali. The crowds lining the barricades are going berserk. You’re in the finishing straight, and Nibali’s just metres in front and you sense that you might be in with a shot … and then finally, amazingly, he runs out of steam.

In the last 100m, you pass the defeated Italian, and your teammate sweeps past you to take the win in a photo finish, just ahead of Alaphilippe and Trentin. Your team has just won Milan-San Remo!



You’re safely ensconced in the peloton as the race hits the bottom of the Poggio. You know this is where the race is likely to be decided so you’re on high alert, ready for just about anything.

A handful of teams have taken it upon themselves to set an infernal tempo on the climb. Riders are being shelled left and right as the kilometres tick by but you’re feeling relatively comfortable near the front of the bunch.

And then, about halfway up the climb, Nibali attacks. There’s still enough riders left in this bunch that chasing him down shouldn’t be too hard, but it is Vincenzo Nibali that’s up front.

What do you do? Do you try to jump across to Nibali (12)? Or do you bide your time for now (31)?


Despite the protestations of your DS in your earpiece, you decide to live to fight another day. You soft-pedal until the peloton absorbs you.

On the run in to a little village, there’s a sharp left turn, followed soon after by a roundabout. There’s a concertina as the riders in front brake to safely navigate the obstacle, flowing around it to the left – the longer way around.

What do you do? Do you follow them to the left (43), or bunnyhop the curb of the roundabout, in an attempt to make up a few positions (49)?


You surge past Bonifazio and take responsibility for setting the pace on the lower slopes of the Poggio. The two of you work well together, swapping off effectively, but it soon becomes clear that your efforts are in vain. Just as the top of the climb comes into view, you can hear the unmistakable sound of whirring wheels and jostling riders behind you. You’re going to get caught.

As you summit the climb, a reduced peloton flies past you at ridiculous speed. As you drift backwards through the field you keep an eye out for your team leader. You’re heartened to see that they’ve made it to the lead group of around 20.

You get out of the saddle and stamp on the pedals, trying desperately to catch onto the back of the lead group. If you can just stay with them over the top, maybe you can be of some use to your leader. But it’s no good — you’re completely spent. As the race rides away from you, you’re left pondering what might have happened had you been a little more patient.

Go to 8.


With a squeal of brakes, you make it around the left of the roundabout and settle back into a steady rhythm, heart still racing. Close call.

The calm conditions of the morning have become less stable. As the race approaches the first feedzone, just before the climb of the Passo del Turchino, you notice dark clouds forming over the back of the hills. It’s getting colder, too.

As the main field rides up the Passo del Turchino, it starts to drizzle. Or that’s what you think at first, anyway. But then the drift of the droplets through the air seems to slow, and you realise that it’s sleet dancing through the air. Despite the pace at which the peloton moves up the climb, you can feel the temperature continuing to drop.

Ahead lies an almost 10 km descent. Decision time.

Do you try to grab a newspaper or vest at the roadside on the top of the climb (36), or drop back to the team car for a jacket and gloves (51)?


With a few hundred metres to go you muscle your way onto Caleb Ewan’s wheel. You reckon he’s the fastest sprinter here so if you can follow him, you’ll give yourself the best chance.

As the four of you thunder down the Via Roma, Ewan opens up his sprint with 200 metres to go. You’re locked onto his wheel just as you’d planned, and you hit the wind with about 100 metres to the line, trying desperately to get in front of the Australian. But he’s just too fast. He’s holding his speed and try as you might, you just can’t get around him.

Ewan crosses the line with his arms aloft, and you follow him across, one bike length behind. Second place at Milan-San Remo. A terrific result to be sure — probably the best you could have hoped for in such an elite quartet.



Your leader might be looking a little worse for wear, but he’s still the leader, and he’s still in the final selection. You position yourself carefully in the remaining bunch, ready to do the best lead-out you can. Your leader settles in safely behind.

You’re the only team with multiple riders left and you’ve played it perfectly. You hit the front with 500 metres to go and give it everything you’ve got. With 200 metres left, your team leader bursts from your slipstream as you drift backwards through the bunch. Your leader hits the line with enough time to throw his hands in the air and celebrate — your team has just won Milan-San Remo!



You back off the pace ever so slightly and wait for your leader to make his way up to your wheel. He’s looking haggard, and is clearly at his absolute limit, but he’s still there, safely in the main bunch.

As you descend off the Poggio you catch a glimpse down the switchback below you and see that Nibali has been caught by the Alaphilippe chase group. Better still, the five leaders are only a few hundred metres ahead of you — this race isn’t over!

Go to 5.


At the last minute, just as the pace picks up to crest the climb and speed down the other side, you reach out a hand for a flapping pink edition of La Gazetta.

You sit up for a second to stuff it down your front, grab a quick drink of water, and settle in for the descent.

You’re grateful for the extra coverage – it’s extremely cold as you descend toward the Mediterranean coast.

Go to 4.


You know it’s important not to panic. It’s important you stay close to Nibali but not at the risk of putting yourself in danger, or spending too much energy.

You start to pick your way carefully up through the field, making sure you’re pacing yourself as best as possible, all while keeping half an eye on Nibali. You know he’s unlikely to attack from this far out, but you need to be near him just in case he does.

Sure enough, Nibali isn’t attacking — he’s just improving his positioning for the challenges ahead.

Go to 17.


You decide that there’s the opportunity to improve your position in the peloton, but it’ll take a bit of a risk – you’ll have to go over the roundabout. There’s a hard concrete curb and a brick-paved inner circle, and you’ll have to get the timing just right.

Just as you’re about to jump, though, your rear tyre gets clipped ever so slightly by a teammate behind you that’s going to the left. You’re able to keep it upright but your timing’s thrown and you plough into the curb. Your front wheel folds, and you tumble over the handlebars, landing heavily on your back.

You lie there for a moment, in a state of confusion. Your instincts are to get back on the bike but a sudden nauseating wave of pain ripples through your body, and as the race doctor runs to your side you black out.



As you cross the top of the climb, you’re surrounded by better-prepared riders zipping up their gilets and jackets. You feel the chill against your chest and are frustrated about your lack of foresight.

Suddenly, you catch the glimpse of a flapping pink edition of La Gazetta out the corner of your eye, and dart across to the left-hand-side of the road. Out of your peripheral vision, you catch a glimpse of maroon and black behind you. Gianni Moscon slams on his brakes to avoid crashing into you, and as you grab the newspaper you hear a torrent of abuse directed your way. You raise a hand in apology, and hope that he’ll forgive and forget.

Go to 52.


You drift out to the side of the peloton and slowly start making your way back through the colourful mass of riders, and then the convoy behind them. You get to your team car and soft-pedal beside the director sportif’s window. He passes you a blacked-out Castelli Gabba, which you put on gratefully.

A gap opens up ahead of you, and you realise that whilst you’ve been talking to the director, there’s a decent gap onto the back of the peloton. “Shit,” he says. “Hold onto the car, you’re gonna get dropped.”

Do you follow his orders (25), or put in a big effort to regain contact (37)?


You tap away comfortably as the peloton snakes its way along the Mediterranean Coast. The breakaway has been caught and you’re entering the next phase of the race. The pace is surprisingly sedate up the first two ‘Capi’ but when the race reaches the Capo Berta, the intensity suddenly lifts. You’ve been instructed to keep an eye on Vincenzo Nibali in the closing kilometres, knowing he’s a dangerman. He’s been very relaxed until now, but as the pace ratchets up on the Capo Berta, you notice Nibali has started to work his way up through the field.

Suddenly, he’s exploded off the front – it’s clear that his plan for the day is an audacious 40 km solo breakaway.

Do you jump on the move straight away (11) or look around for a helping hand with the chase (16)?


There’s no time to wait around for a leader that’s struggling. You have to go. Now.

You sprint out of the pack in the closing kilometres of the Poggio and bury yourself to get across to Alaphilippe, Gilbert, Trentin and Van Aert. You’re relieved to see that no one has made it across and you make contact just at the summit.

The five of you barrel down towards the coast, taking all sorts of risks in search of the dangerous Vincenzo Nibali. It’s a struggle to stay with Alaphilippe in particular who is descending like an absolute madman.

But all five of you make it to the bottom safely and there, just ahead of you, is Nibali. You catch the Italian with a kilometre to go setting the race up for a six-man sprint.

As you fly into the final 500 metres, you look around at your rivals, knowing that everyone here — except Nibali perhaps — has a very fast finish. By your reckoning though, Alaphilippe and Van Aert are looking the freshest.

So, how do you play it? Do you follow Alaphilippe (7)? Or do you sit on Van Aert’s wheel (27)?

The End

Thanks for playing along. We hope that you are at peace with your 2020 Milan-San Remo result.

Want another ride at Tour of Flanders? Let us know in the comments below …

The images you see in this story appear courtesy of Kristof Ramon, The Grubers, Cor Vos and Kei Tsuji.

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