I’d heard the hype and wanted to see what all the fuss was all about; to ride the trails where the pros went in winter. I just neglected to remember one crucial thing before setting off. I’m no pro on the bike, of course – hence the journalism – and when it’s not your day, it’s not your day.

Crash number one sent me over the handlebars a solid 90 seconds or so after I got going on the bike, on some fun and flowy but relatively simple singletrail with one hell of a stunning backdrop – looking down a spectacular canyon and out over the third-highest peak on the island.

“It’s just the first line of the day,” I told myself, “and you do have a habit of getting distracted by a good view or a fly or an oddly shaped cloud for that matter. Focus. It’s all up from here.” In truth, that would be by far the most comfortable crash of the day.

We flow through dusty trails and low-cut bushes, coming out on a dirt road to ride a short distance and look over a sizeable patch of terrain burned into oblivion by a shocking recent forest fire in Madeira. The fire burned through 10 percent of the trails on the island John tells me, but there’s so many kilometres more to ride that there’s no chance of it affecting the tourism. A quick turn and we’ve traded dust for mud and forest to ride a rock-and-root downhill track so new it took John a moment or two to find the entrance.

John took off and whizzed through the new trail ahead, not quite ridden in yet, and it starts to become blatantly clear why the place is becoming so renowned for riding. You could almost picture the pros splashing dirt around the berms and blasting down the rocky terrain.

The signature stamp on the day would come later though, on the aptly named ‘Risco’ trail, descending around some precipitous turns before dropping down a staircase lined on one side by an angled forest and on the other by an exposed cliff-face staring out into open water, and dropping what must have been around 1000m to the seabed below.

“It’s good to see the government have opened their eyes and seen that the island is not just for retired people…”

“Please be sure of yourself here,” begs John, continuing his bid to try and keep me alive. It’s been touch and go so far, so I don’t blame him for the reminder.

The trail has got to be one of the most remarkable on the planet. The Enduro World Series riders will be taking it on next May, and it wouldn’t be a surprise if the snaps that follow elevate Risco to a coveted fame, stapled on bucket lists and fetishised on film screens the world over.

You don’t have to be pro to enjoy Madeira, though. We ride on past a river and jump in the van which drops us off at what will be another segment of the EWS Series course. It’s more casual; flowing through dirt trails between high-reaching trees; another change of scenery on a route that seems to change backdrop quicker than a green screen.

By the time we reach lunch we’ve only been riding a few hours but it seems like we’ve sailed through three continents, and there’s no doubt about it; I’ve taken quite the beating. As I get out the van for lunch I shut the door behind me and the window frame inexplicably falls out of the vehicle into the seat behind. It’s been that kind of a day. “Don’t worry,” laughs the endlessly patient John. “We can fix that.”

My hands are glad for the chance to stop shaking and ask John a bit more about Freeride Madeira and the changing nature of the tourism in his hometown. He happily obliges:

“It’s incredible how much we’ve made Freeride Madeira grow in the past two or three years. We’ve got a really good team. Everyone puts their lives and hearts on it and we work really hard from sunrise to sunset which is why it’s developed so quick.

While I’m relatively new to surfing, Orlando was glad to point out that while there are only three real spots to learn to surf on the island, there are a whole lot more where the waves can stretch up to 15m and do some serious damage if you bail, and the line ups are nearly always empty.

This is an island where not even experts are going to run out of options no matter what their sport, and Orlando and Nuno, the latter of whom is currently doing a PHD in tourism, want more people to know it.

“There is so much more to the island than that,” Orlando bemoans of the old-age tourism, and it’s so obvious that he’s right that it’s a wonder it ever got this far. You can’t drive five miles without being overshadowed by a dramatic mountain range or coming across wanderlust-inspiring waves crashing against the coast.

“We need a mix of tourists,” says Nuno. “Pensioners have time and money but they don’t want to see the levadas [mini-canals]. They come because we have weather all year round.

“More young people are coming to the island now that want to see the nature. It’s a new kind of tourist. People used to decide where they’re going two months in advance, now they’re deciding where they want to go tomorrow. We have hotels with cheap prices and youth hostels for travellers though. We’re going in the right direction.”

In the few days I would spend in Madeira I would see both sides of the Madeira juxtaposition; from the old-age comfort to the full-on nature of the adventurous chaos.

See, the rest of our group were more focused on sampling the wine and fine dining in the region than the sports. This meant that by day I would be catching waves, tackling canyons or staring wildly at trails capable of taking our heads off and dropping our jaws, before returning to Funchal to sip on a selection of wine that came in more shapes and sizes of wine glass than I was aware existed.

It was one of the most bizarre contrasts I’ve ever experienced between day and night.

Each evening over dinner I’d be filled in on the rest of our crew’s relaxing day knocking back wine and watching dolphins, to which I could only mumble my daily injury list in reply as I tried to ascertain for sure whether we had indeed spent the day on the same island.

Remove the plethora of hotel resorts crowded around the city centre and Madeira is a wild beast with a mysterious aura; an adventurous utopia with secrets that can only be discovered through exploration which inspires excitement. Truth be told, we only wish they had never built the resorts at all. Without them, the entire place would be a playground worthy of fiction.

Madeira may be known as a sun-soaked setting best for rest and relaxation for now, but with the adventure options on offer, there’s only so long that that limited tourist tag can last. The other side of Madeira is erratic, exciting and at times dangerous. And it’s only going to continue to grow.

Read the rest of our November ‘Other’ issue here

Monarch, the scheduled leisure airline, operates year round flights to Madeira from Birmingham and London Gatwick airports with fares, including taxes, starting from £59 one way (£109 return).

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