After ten unforgettable days in Madeira, we quickly realized there was no way this trip could live in a single blog post. So I’m breaking it up—starting where our journey began: Funchal. We arrived here straight from Lisbon after spending two laid-back weeks in Ericeira, and the contrast hit us immediately. Where Ericeira felt calm and coastal, Funchal burst onto the scene with color, movement, and dramatic scenery. Nestled between the Atlantic Ocean and steep, green mountains, Funchal is Madeira’s capital and cultural heart—equal parts historic charm and vibrant island life. From the moment we landed, we were completely blown away by how beautiful it was.

#1 Must-Do: Ride the Funchal Cable Car

We spent three full days soaking up Funchal, and they were packed with some major highlights. One of our very first adventures was riding the Funchal Cable Car—an experience that instantly set the tone for the trip. We floated up and away from the city, gliding silently over red-tiled rooftops, lush gardens, and the sparkling harbor below. With every passing minute, the views seemed to outdo themselves, stretching farther across the Atlantic and deeper into the green hillsides that wrap around the city. By the time we reached Monte, it felt like we’d climbed into an entirely different world—quieter, cooler, and impossibly scenic. We opted for a one-way ticket, which at the time felt like a casual choice… but trust us, there was a very good reason for that, and you’ll see why later.

#2: Explore Monte Palace Tropical Garden

At the top, we explored the Monte Palace Tropical Garden, a sprawling hillside paradise filled with exotic plants, tropical flowers, geometric terraces, ponds, water features, and sweeping views over the city and ocean. The gardens are massive, immaculately maintained, and surprisingly peaceful—one of those places where you keep saying, “Wow,” every few steps.

While exploring the gardens, we stumbled upon one of those unexpected travel gems: a small, incredibly welcoming cafeteria tucked into the hillside. It was the perfect place to refuel—with food and wine—while soaking in the view from outdoor tables that looked straight down to the ocean below. We were very high up, which somehow made that glass of wine taste even better. Sitting there, surrounded by flowers and fresh mountain air, with the Atlantic stretching endlessly beneath us, felt like a pause button on the day.

One of our favorite spots in the gardens was a dreamy water feature with mossy, green walls and a cascading waterfall that felt almost enchanted. Two paths led through it: one dry, one very much not. And, unsurprisingly, three of us immediately chose the wet path. The boys ran straight through the waterfall, laughing the whole way, and emerged on the other side absolutely soaked—shoes, clothes, hair, everything. It was spontaneous, ridiculous, and perfect… one of those memories that ends up meaning more than any photo ever could.

#3 Say Yes To A Wicker Basket Toboggan Ride back down

And then came the adrenaline. We did the tourist thing, which we don’t always do, and waited in line for about an hour. I have to say this time it was worth the wait. From Monte, we hopped into one of Madeira’s most unique traditions: the wicker basket toboggan ride. Guided by skilled carreiros in straw hats, we sped downhill through narrow streets in a wooden sled lined with wicker, using nothing but their boots to steer and brake. It was fast, slightly chaotic, and completely exhilarating—an experience that felt both historic and wildly fun. We were dumped out near the bottom, somewhat where we started that morning, and strolled the rest of the way home.

Check out this experience!

#4 Get Out of Town & Take a Tour Through Get Your Guide (Ask for Susanna!)

On one of the days in Funchal, we wanted to experience more of the island’s interior and dramatic coastline. So we booked a full-day tour through GetYourGuide — and that’s how we met Susanna.

We expected to be part of a small group tour, but when the morning arrived it turned out we were the only ones booked that day. Just like that, we had our own private guide for the island.

Our climb out of Funchal toward the mountains was nothing short of wild. The roads grew steeper and narrower with every turn — twisting upward through tiny villages and terraces clinging to the hillsides. At several points I honestly wasn’t sure the car would make it up the incline, but Susanna laughed and assured us that cars on the island are built differently — many equipped with special gearing designed for Madeira’s famously steep roads.

We were surprised to even see houses perched along these slopes. At one point Susanna pointed across a distant hillside and told us that one of the homes there was where Cristiano Ronaldo grew up. That definitely caught the boys’ attention.

Eventually the road leveled out as we climbed higher into the mountains. The air cooled, the vegetation changed, and before long we pulled over at a viewpoint where we were suddenly above the clouds.

Our next stop was one of the places we had been most excited to see: Pico do Arieiro.

At 1,818 meters (about 6,000 feet), Pico do Arieiro is the third-highest peak on Madeira and one of the island’s most famous viewpoints. Jagged volcanic peaks rise dramatically from a sea of clouds, creating a landscape that feels almost surreal. It’s also the starting point for one of Madeira’s most legendary hikes — the trail connecting Pico do Arieiro to the island’s highest summit, Pico Ruivo.

We didn’t hike the full route, but we spent plenty of time wandering the paths around the summit, soaking in the views of the rugged mountains stretching endlessly in every direction.

From there, the scenery changed completely. As we descended from the peaks, the dry rocky landscape gave way to dense greenery and mist. The road wound into something that felt almost like a rainforest.

We had arrived in the lush valley of Ribeiro Frio to hike the famous Levada dos Balcões.

Madeira’s levadas are one of the island’s most unique features. Built beginning in the 16th century, these narrow irrigation channels were designed to transport water from the rainy northern mountains to the drier southern farming regions. Today, thousands of miles of levadas crisscross the island, and the maintenance paths alongside them have become some of Madeira’s most beautiful hiking trails.

The Levada dos Balcões is one of the easiest and most rewarding. The trail winds gently through dense laurel forest — part of Madeira’s UNESCO-listed Laurisilva — until it reaches a spectacular viewpoint overlooking a deep valley and the island’s highest peaks.

Everything around us was incredibly green. Moss covered the rocks, water trickled quietly beside the trail, and fog drifted through the trees.

After our hike, Susanna suggested we stop for lunch at a small cliffside restaurant — the kind that doubles as the owner’s home. Our table sat right on the edge of the forest, with sweeping views over the lush valley below. It was the kind of setting that makes you linger long after the meal is finished.

Next, we continued on to the charming village of Santana, famous for its traditional Madeiran houses.

*A stop in Santana, Madeira to see the traditional A-frame houses (can you spot them in the background?)*

These triangular cottages, known locally as casas de colmo, are instantly recognizable. With their steep thatched roofs that extend almost to the ground and their brightly painted red doors and blue window frames, they look like something out of a storybook. Historically, these homes were built by farmers using local materials like wood and straw, designed to withstand the island’s wet northern climate.

Today, they’ve become one of Madeira’s most iconic cultural symbols.

From Santana we followed the rugged north coast westward, stopping frequently at viewpoints Susanna recommended along the way.

One of the most memorable stops was in Porto da Cruz. The coastline here was absolutely stunning — dramatic cliffs dropping into the Atlantic and waves crashing against black volcanic rock. The landscape reminded me of a mix between the Hawaiian islands of Oahu and Kauai.

We even made a quick stop for a rum tasting — something Susanna insisted we couldn’t miss. Madeira has a long history of sugarcane production, and traditional sugarcane rum (aguardente de cana) is still produced on the island today. While Chip and I sampled a few varieties, Susanna enjoyed coffee on the terrace with the boys.

Our final scenic stop of the day brought us toward the eastern end of the island to a viewpoint above Caniçal.

From this vantage point, the landscape looked completely different once again. The lush green mountains we had been exploring gave way to a drier, more rugged coastline with sweeping ocean views and dramatic cliffs stretching into the distance.

It was a perfect reminder of just how incredibly diverse Madeira is for such a small island.

By the time we returned to Funchal that evening, we felt like we had traveled through half a dozen different landscapes in a single day.

And little did we know, this wonderful guide we had met — Susanna — would soon become part of even more adventures when we headed north to Seixal.

Encore #5: Slow Down in Funchal

The last full day in Funchal was spent slowing down and enjoying the simple pleasures. We wandered through town, did some damage at Ale-Hop (hands down one of the best stores for kids and adults), played chess in the square, sampled Madeira wine, and just let ourselves get lost in the rhythm of the city. Funchal has a way of pulling you in—whether you’re chasing views, history, or just a good place to sit and watch the world go by—and it was the perfect introduction to everything Madeira has to offer.

Just you wait…There’s MORE!!!!

As much as we fell in love with Funchal—the views, the energy, the food, the traditions—we knew it was only the beginning of our Madeira adventure. Those first few days gave us a taste of the island’s charm, but what came next took everything to another level. The second half of our trip was spent in Seixal, in a home perched in what might truly be the most beautiful place on earth. And somehow, it just kept getting better.

Stay tuned for black sand beaches, the tour guide that we loved so much we booked her twice, mountains that seem to cascade straight into the ocean, views for days, and a journey to the very top of the island—wandering through Fanal Forest, a mist-covered, otherworldly landscape that felt pulled from a dream. Trust me… the adventure has literally just begun.

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