Mid-Atlantic Maneuvers

With the chance to tick off not one but two foil-related ambitions in one hit, Diogo Neves got planning for a downwinder channel crossing in Madeira that would challenge even the most seasoned epic downwinder specialists…

Words: Diogo Neves & James Casey
Photos: Pedro Vasconcelos & Bruno Chícharo

The Challenge

Diogo: I had I had two foiling dreams.

The first was to cross the island channel from Porto Santo to Madeira, and the second was to meet and share some downwinders with my online foil coach from the other side of the world, James Casey. So I thought, why not do both at once? I challenged James to come to Portugal the next time he was in Europe, and he told me he'd be in the UK in the summer of 2024. That was my cue to get things rolling. I reached out to my contacts, and soon I was planning a “double-dip” in Portugal, where I could share and explore the foiling conditions of my two hometowns with James: the windy Viana do Castelo in the north of the mainland, and the semi-tropical Madeira Island, just off the Moroccan coast.

Our first stop was Viana do Castelo, where we stayed at the wonderful FeelViana Sports Hotel, right by the beach. We had an amazing time, catching some decent foiling waves and managing a few light and short downwind runs (despite not being too lucky with the forecast). James also held some fantastic foiling clinics for local riders and hotel guests.

Next, we headed to the beautiful Madeira Island to explore its foiling potential, but more importantly, to tackle the main event – the channel crossing between the two inhabited islands of the Madeira archipelago: Porto Santo and Madeira.

With its subtropical climate and warm waters year-round, Madeira is a foiling paradise, offering the chance to wing and downwind five to six days a week in almost any wind direction, as the island catches nearly all winds thanks to its varied coastline. While Madeira is famous for its world-class big wave point breaks on the northwestern and southwestern sides, fewer people know about the winging and downwinding potential on the south side. The southeast and southwest coasts provide excellent conditions for both flatwater and bumpy rides, with downwind runs ranging from friendly 5–10km rides to more challenging 25–50km adventures, depending on the wind's direction. The further east or west the wind shifts, the longer the runs you can take. Easy access to coastal roads, with options to enter or exit every 3–5km, makes it all very practical and accessible.

The most common northwest or northeast swells wrap around the island's southern coast, aligning parallel to the shore and creating fairly friendly conditions for an otherwise wild, mid-Atlantic island. That said, the rides can still be challenging and technical at times. With flatwater sections, clever line choices are required, especially when faced with side shore winds or the dynamic energy around capes and headlands, which bring strong currents and backwash. These ever-changing conditions demand the best of your foiling skills, and you'll need the right equipment to harness the ocean's energy and glide through it all.

My Personal Journey

Coming from a surf and SUP background, my first real exposure to foiling happened just after the COVID lockdown. I went on a 14-foot SUP race downwind run with a local crew, including Tiago Campos. Tiago was on a custom SUP with a foil that was 6’5 x 28”! After we paddled out to reach the wind line, I was struggling to catch a slow bump when I saw Tiago take off in front of me. He was flying away in what seemed like a kind of magical suspension, carried by the ocean’s energy, the wind, and – at least to my eyes – maybe even God Himself! At that moment, I knew I wanted to experience that magic for myself.

I bought some wingfoil gear and took my first steps into foiling. I enjoyed it, but it wasn't enough to keep me hooked at first – the back-and-forth of tacks and gybes wasn’t really my thing. What truly called to me was bump riding, especially downwind. That felt like freedom to me, the challenge of reading the ocean and deciding exactly what to do and when. I loved how it combined physics, math, and kinetics, all playing out in my mind as I tried to understand and respond to the forces at work. From the very start, I relished that intellectual and physical challenge. I felt that I needed to be completely connected with the ocean’s energy to be efficient and succeed, and I thrived on that challenge. I still had that image in my mind of someone paddling up on foil and flying away downwind, like something out of a dream.

Naturally, storing the wings in my garage and picking up a SUP foil board to try it in the waves became the next step. But I needed guidance to progress. Tiago Campos, my old SUP racing partner, was an early downwind foiling pioneer in Portugal, and he helped me a lot – sharing tips on conditions, gear, and so on. At that time, he was the only one trying and actually succeeding in downwind foiling in Portugal. Still, it wasn’t quite enough, especially since he was based on the mainland. I felt like I needed more guidance to really improve.

That’s when I found James Casey’s Coach Casey Club Course online. It was incredibly well-designed, offering theoretical modules with great videos, a private Facebook group filled with shared information about gear and technique, and a weekly Zoom call where James and the group would analyze footage and photos and ask questions. James has a natural teaching gift. His keen eye can pinpoint what’s working and what’s missing, and he provides feedback in a very practical, understandable way. That course helped me enormously, even back in the early days when boards were larger and more challenging. Those were tough days, but thanks to James, I kept progressing.

Preparing for the Crossing

First, I have to say that the idea for the Madeira Foiling Adventure and the channel crossing would never have been possible without the support of Madeira Tourism, my local club, Clube Naval do Funchal, the friendly Madeira Coastguard, and a few local sponsors who believed in the adventure.

We planned the crossing for nine people – both well-known invited foilers and local crew. Along with James and myself, we invited Tiago Campos (of course!), the legendary French waterman Fred Bonnef, and the half-Viking, Casper Steinfath, though Casper unfortunately had to cancel last-minute. So, the four of us would be SUP foiling the channel, while five locals would be winging it. Among the locals was Ricardo “Sapo” Rodrigues, my water and clubmate, who helped organize the event. As soon as we arrived on the island, James and I met up with the local crew to decide on the best day for the crossing. Fortunately, we had a couple of days ahead with strong northeast wind and swells – exactly what we needed. We had to choose between going on the first day with stronger winds and less swell or waiting for the second day with lighter winds but bigger, more energized swells. As some of the group was arriving late the night before, we decided to wait and go on the second day. The channel conditions were somewhat unknown. Local sailors and Olympic windsurfing athlete João Rodrigues, who had previously completed the crossing on a windsurf foil, shared their insights with us. They told us to expect prevailing north currents, constantly shifting wind and swell conditions, and strong backwash upon our approach to Madeira.

On the day of the crossing, we took the ferry to Porto Santo early in the morning. Along the way, conditions already looked challenging: strong wind, long-period swells, and powerful currents. It was clear that this wouldn’t be easy. During the ferry ride, we met with the captain to discuss the conditions further, including potential issues with currents, hidden reefs, and the best route lines to take. Following the ferry were three escort boats, trying to shelter themselves from the harsh wind and swells. Unfortunately, one of the boats had to abort the mission due to the conditions, so we had to adapt our safety plan to rely on just two boats. This created an extra challenge, as we needed to balance the pace of all participants – both the SUP foilers and the wingfoilers.

When we arrived at Porto Santo, with its stunning golden beaches, we headed to the remote and rugged Morenos spot, where we would launch. We had to navigate our gear down to sea level through a steep goat track, which required the whole team to work together. It wasn’t just about the adventure – it was a necessity!

The Crossing

James: The crossing from Porto Santo to Madeira was an incredible challenge. Starting with the scramble down the rocks, to the rocky beach setup and a wind shadowed start. There was a 200m gap where wind and waves created enough bump to start but it was straight into an 800m pump to get wide enough of a tall island which created the wind shadow. Out wide there was a crazy amount of long period energy mixed in with moderate wind bumps. This was a precursor of what lay ahead. A challenging yet enjoyable day of downwind foiling. 

The start was beautiful but wild, long period energy where you were literally hooting and hollering in between maneuvering two or three different swell angles. In between the wedging swells and you were flying, almost over-foiled as you gazed at the beauty of Porto Santo, if you were out of sync it was hard work pumping between overhead bumps.

The second section the wind turned more west as we approached Madeira. Backwash off the steep, rocky uninhabited side of the island meant you could just about go any direction except the one we needed to go, it was all a mess until all of a sudden it wasn't! The current off the beautiful yet baron national park changed and the wind was so west it was basically offshore, pushing us towards Ilhas Desertas to the southeast. This was a serious mental battle. I was using a shorter than normal board, a 6'10 Sunova Aviator. If I came down in the backwash it would not be easy to start my Code Foils 860R, if I came down in the current affected flatwater it would be risky, getting stuck in an eddy taking you the wrong direction. The only option was to keep going, paddle and pump until the current changed and the bumps reappeared.

Finally the third section showed its face. Eerily similar to the last 10km of the Molokai 2 Oahu 2024, wind slightly offshore, bumps slightly onshore. A playful yet technical section, with 50km in your legs, it is not the easiest type of bumps. The orange roofs of inhabited Madeira began to come into view and you knew it wasn't far – a surf in to shore with a little bit of offshore breeze in your face.

Personally I loved the course, the variety really showed who had done the work and who had just trained when the wind was up. I think it is a great course to run a race. It is a decent distance that will make it truly challenging, mixed conditions will test all riders and the picturesque scenery along the way will have everyone pinching themselves. I'll be back to give it another crack, hopefully in a racing format as I truly believe any aspiring downwind foil racer should experience the rugged beauty of Madeira.