I hiked The Madeira Trail: My 5-day coast-to-coast journey

Madeira had been on my radar for a while. Not because I was actively looking for it, but simply because my Instagram feed was flooded with it. Lush green cliffs, cascading waterfalls, and views that looked almost unreal. And every single time, I thought the same thing: I need to go there.

For those unfamiliar with the island: Madeira is a tiny Portuguese dot in the Atlantic Ocean, actually closer to Africa than to Lisbon. It’s volcanic, incredibly green, and so surprisingly diverse that it’s hard to believe it all fits onto one single island. One moment you’re standing on a mountain peak high above the clouds, the next you’re walking along cliffs that plunge straight into the ocean. And the best part? Tucked between all those famous highlights are countless hidden gems where you’ll hardly meet a soul.

Let me introduce ourselves, because I’m not doing this alone: I’m hiking this trail together with my boyfriend. We’re both avid hikers, but we also appreciate our comfort. Adventuring to the fullest during the day, and crashing into a warm, cozy bed at night, that’s our ultimate combination. No tents, no sleeping bags. Just muddy boots during the day and a good glass of wine with dinner.

And that’s how we ended up choosing The Madeira Trail: a multi-day trek where you hike from accommodation to accommodation, taking in both the famous highlights and the quiet, hidden spots. And I’ll let you in on a secret right away: it did not disappoint.

We spent the first night at the hotel offered as an option by the trail organizers. Small detail, big difference, because it meant we woke up exactly in the right spot for the morning shuttle to the starting point. We had our breakfast and off we went.

We set off in the sunshine and arrived in the drizzle. Madeira had officially introduced itself. The island has so many microclimates that you can easily experience all four seasons in a single day. The north side is lush and wet, the south is dry and sunny, and the mountains in between just make up their own clouds.

As it happened, that moody weather was the perfect setting for the Fanal Forest. Picture this: ancient, gnarled laurel trees, mist drifting between the branches, and a soft, steady drizzle. This forest is hundreds of years old and is a UNESCO World Heritage site. It felt less like hiking and more like walking through a fairytale where an elf could pop out at any given moment.

After about half an hour, we left the forest behind, and there waiting for us was the island’s other main character: the stairs. On Madeira, these stairs follow one golden rule: no two steps are the same height. Your legs never quite know what’s coming, and by the end of a climb like that, you definitely feel it. But you know what? It didn’t matter. There is something wonderfully simple about a day where your only task is: left foot, right foot, repeat. No emails, no notifications, just you and the next stretch of trail.

By late afternoon, things started getting busier, the universal sign that something beautiful is just around the corner. And sure enough: a waterfall. We quickly snapped a few photos and then set off on the home stretch toward our cottage in Rabaçal. Waiting for us there were a coffee and a pastel de nata, which taste like a minor miracle after a full day of walking. Mind you, we weren’t done hiking just yet; after a quick break, we headed out again to visit a second waterfall. The evening ended exactly as it should: pasta, a glass of wine, and a good chat with the group.

Day two began just like day one: a light sprinkle of rain, a veil of fog. But that didn’t make the hike any less beautiful. We followed a series of levadas, those typical Madeiran water channels with a narrow path running alongside them and spotted a surprising number of birds along the way. Walking along a levada has a meditative quality. The water ripples alongside you, the path stays nice and flat, and your mind clears on its own.

The fog lingered for a long time. It wasn’t until around three o’clock that it started to clear, and that happened to be the exact moment we arrived at the most beautiful viewpoint of the day. We stood there, ready to be blown away, and saw a gray wall. Nothing. So we did what every hiker does in such a situation: sat down and pulled out some snacks.

And then, as if Madeira suddenly took pity on us, the sun broke through. First a sliver, then more, and then suddenly the entire valley lay wide open, as if someone had drawn back the curtain just for us. Lesson learned: on Madeira, patience always pays off. Wait fifteen minutes, and the whole landscape changes.

Dessert of the day: two tunnels, carved right through the mountain back when the levadas were built. We knew they were coming, but when we stood in front of the entrance, we still thought for a moment: do we really have to go through there? A small black hole in the rock face, with the water flowing right next to it. So we took a deep breath. Headlamps on, and we stepped the first few meters into the darkness and after that, it actually turned out to be quite fun. All you can hear is the water splashing and the muffled sound of your own footsteps. It was something completely different, and that’s exactly what makes it so memorable.

After 25 kilometers, we arrived at the hotel, feeling that wonderful kind of tiredness that lulls you into a contented sleep at night. And that first hot shower after a long day of walking? Few things can compare to it.

Today was the big one: Pico Ruivo, at 1,862 meters the highest point on the island. The shuttle dropped us off at the starting point, where the sky was completely overcast. So we did the only sensible thing and ordered a coffee at a cozy little bar first. And just as I picked up my cup, the sky opened up. My backpack has never been back on my back so quickly.

A little less than an hour later, we were at the summit. On clear days, you can see all the way to the sea from here, with mountain peaks jutting out like little islands above a blanket of clouds. For us, sun and clouds took turns like a shift schedule, but we could certainly call it a successful view.

Next came my favorite part of the trail: the descent to Ilha, where almost no tourists go. One moment you’re sharing the summit with half the world; the next, you’re walking in such silence that you wonder if everyone has left the island without telling you. And that’s exactly what makes this hike so magical. We celebrated the end of the descent with a poncha and meat on a stick. That poncha is the local specialty: rum, honey, lemon, and sugar, hand-whisked into something dangerously delicious. Madeira’s answer to sore legs. Well-deserved and then one more.

Finally waking up under a clear blue sky. Shorts on, sunscreen on my nose, and off we went. A short while later, we reached the coast, with the mountains behind us and the ocean ahead. Madeira has this strange ability to completely change the scenery within a single hike, from misty mountain forests to cliffs overlooking azure waters.

It was going so well that we decided to take an extra loop to a headland. Did we slightly underestimate it? Yes, absolutely. But once we reached the bottom, every cursed meter was immediately forgotten. For the last 500 meters of elevation gain, we turned on the music and practically danced our way up. The reward: a room with an ocean view and a jacuzzi. I’ve rarely slid my feet under a table feeling so content.

Time flies on The Madeira Trail. Before you know it, you’re on your last day of hiking, another glorious day along the coast. This was a more popular stretch, so there were more people around, but with the sun shining on your face, nothing can get you down. The kilometers just melted away, and suddenly we were in Machico, the end of the trail. Time to celebrate with an ice cream on the beach, of course.

The trail was officially over, but my legs didn’t think so. We had one extra day, and ranger Natacha recommended Pico Grande. Challenging, but with a view of Pico Ruivo. One last tough hike, with a view as a reward. Exactly how it was meant to end.

What makes The Madeira Trail so great is that it’s self-guided. No guide leading the way and keeping track of the time, no schedule rushing you along. You decide your own pace, your breaks, and how often you stop to photograph that same mountain for the 10th time. And yet you’re never on your own: there’s occasional luggage transport to your next lodging, the route is mapped out, and the ranger is always available for questions or if anything goes wrong. Freedom without the stress.

There were ten of us on the trail, a mix of languages and ages. You share the same trails, the same fog, and the same wild joy when the sun finally breaks through. That forges a bond.

Madeira is made for hiking. The flowers, the mountains, the sea: for me, it had it all. Along the way, we struck up a conversation with a few people who were touring the island by car. Their biggest pet peeve? You can hardly hike in loops there, so if you’re driving, you end up retracing your steps along the same stretch every time. I hadn’t even thought about that beforehand. But that’s exactly what makes The Madeira Trail so special: you never walk the same path twice. Each day begins where the previous one ended, and that way you see the island slowly change beneath your feet.

And no, I’m not going to lie. It was tougher than I thought. At a certain point, you can feel the elevation gain and those nasty, uneven steps all the way down to your toes. But what you get in return easily makes up for it: hiking above the clouds, a valley that opens up at just the right moment, a poncha that tastes like victory. And best of all: you earn every view with your own two feet. That makes it twice as beautiful. Who’s this for? For anyone who loves to hike, doesn’t shy away from a steep climb, and really wants to see the island: slowly, on foot, up close. You don’t have to be a mountain goat, just be in decent shape and in good spirits. Not sure if you can handle it? I had those doubts too, and in hindsight, they turned out to be completely unfounded. I came home with sore legs, a head full of beautiful images, and above all, the urge to book the next trail right away.

So. Go ahead and pull those hiking boots out of the closet, because Madeira is waiting.