5 Days in Madeira: A Dreamy Escape to Portugal’s Island Paradise

The moment I set foot in Madeira, I knew I was somewhere extraordinary. Floating in the Atlantic Ocean off the northwest coast of Africa, this Portuguese archipelago felt like a world apart—lush, dramatic, and beautifully timeless. What followed was five days of discovery, where volcanic mountains met crashing waves, and every corner promised another postcard-worthy view.

Day 1: Arrival in Funchal – A Warm Island Welcome

My journey began in Funchal, the vibrant capital of Madeira. From the moment I arrived, the city’s charm was undeniable—colorful buildings climbing the hillsides, jacaranda trees in bloom, and the ocean shimmering just beyond.

I checked into Castanheiro Boutique Hotel, a chic spot in the heart of the old town. The rooftop pool offered panoramic views of the city and the Atlantic—perfect for a post-flight dip.

After settling in, I wandered through the cobbled lanes of Zona Velha (Old Town). Murals on painted doors gave the narrow alleys a bohemian vibe. I dined at Restaurante do Forte, a romantic spot in an 18th-century fortress, where I savored fresh scabbardfish with banana, a curious and delicious local specialty.

Day 2: Monte, Toboggan Rides & Botanical Bliss

No trip to Funchal is complete without riding the cable car to Monte. Suspended high above the city, the views were jaw-dropping. At the top, I explored the Monte Palace Tropical Garden, filled with koi ponds, azulejo tiles, and exotic flora from around the world.

But the real thrill came with the toboggan ride—a tradition dating back to the 19th century. Sitting in a wicker sled steered by two men in straw hats and rubber boots, I slid down the steep streets of Monte back toward the city. It was equal parts hilarious and exhilarating!

That evening, I relaxed with a glass of Madeira wine at Blandy’s Wine Lodge, where I also took a brief tour to learn about the centuries-old aging process. Dinner was at Armazém do Sal, a modern fine-dining gem blending local ingredients with international flair.

Day 3: The Wild North – Santana and Forest Trails

On day three, I rented a car and ventured into the wild, verdant north of the island. The drive was dramatic—hairpin curves hugging sheer cliffs and tunnels slicing through rugged mountains.

My first stop was Santana, famous for its traditional triangular thatched houses. These fairytale cottages made for great photos, but the real magic was in the surrounding nature.

I hiked a section of the Levada do Caldeirão Verde, one of Madeira’s iconic irrigation channels that double as hiking trails. Surrounded by emerald forest, waterfalls, and mossy rocks, it felt like walking through a dream.

Lunch was a rustic affair at Cantinho da Serra, where I enjoyed a hearty espetada—grilled beef skewers cooked over wood and served with fried maize and garlic butter.

Back in Funchal that night, I grabbed a drink at Reid’s Palace’s famous Cocktail Bar, where Winston Churchill once sipped scotch. The oceanview terrace was the ideal place to toast another unforgettable day.

Day 4: West Coast Wonders – Cabo Girão & Porto Moniz

With my rental car still at the ready, I drove along Madeira’s spectacular west coast, stopping first at Cabo Girão, one of the highest sea cliffs in Europe. The glass skywalk platform here isn’t for the faint-hearted—but the view over the terraced hills and crashing waves below was worth the nerves.

Next was a scenic drive to Porto Moniz, known for its natural lava pools. I spent a few hours swimming in the crystal-clear waters surrounded by black volcanic rock and watching waves crash nearby. It felt like nature’s spa.

On the return drive, I passed through Seixal, where a black sand beach and lush cliffs tempted me into a spontaneous sunset stop. I walked barefoot along the shore, completely alone but utterly connected to the island.

Dinner that night was laid-back and delicious at Casa de Pasto Justiniano, a no-frills, family-run place where locals eat. I tried lapas (limpets) grilled with garlic and lemon—simple but unforgettable.

Day 5: Farewell Funchal & Last-Minute Joys

For my final day, I wanted to keep things relaxed. After breakfast on the terrace, I wandered the Funchal Market (Mercado dos Lavradores)—a feast for the senses with exotic fruits, handmade crafts, and fragrant flowers. I picked up a few souvenirs, including bottles of passion fruit liqueur and a locally woven straw hat.

Before heading to the airport, I squeezed in one last walk along the Promenade do Lido, where palm trees swayed beside seaside cafés. I stopped for one final pastel de nata and espresso, soaking in the salty breeze and sunshine.

As the plane ascended and the island shrank below, I felt a deep sense of gratitude. Madeira had offered me so much in just five days—adventure, serenity, warmth, and wonder.

Travel Tips for Visiting Madeira

• Best Time to Visit: April to October for warm weather and clear skies.

• How to Get Around: Rent a car for day trips beyond Funchal. Roads can be narrow and steep—drive cautiously.

• Must-Pack Items: Hiking shoes, swimsuit, layers (weather changes quickly in the mountains), and a camera!

• Don’t Miss: Levada walks, natural pools in Porto Moniz, a toboggan ride, and Madeira wine tasting.

Final Thoughts

Madeira is a place where nature’s drama meets Portugal’s soul. It’s not just a beach destination—it’s an invitation to explore, to taste, and to feel alive. Whether you're an adventurer, a foodie, or someone in need of rest, this island delivers a rich and unforgettable experience.