Madeira Island Traverse

Our island traverse begins with a classic coastal hike along Madeira’s iconic levadas, the historic aqueducts that wind across the island’s steep terrain. Starting in town, we follow these gentle pathways as they guide us gradually upward along the valley slopes before reaching dramatic seaside cliffs with sweeping ocean views.

From here, we continue along the rugged northern coastline on an undulating trail, eventually arriving in the charming seaside town of Porto da Cruz. After time to explore, we transfer to Santo da Serra and our hotel for the night. Tomorrow, we head inland as the terrain—and intensity—begins to increase.

Today we hike along the Levada da Serra do Faial, continuing on to Levada do Furado, one of Madeira’s most scenic levada routes. The trail winds through tunnels carved into the mountainside and passes waterfalls and quiet pools, all beneath the dense canopy of the island’s lush Laurisilva forest.

This ancient laurel forest is one of the best-preserved of its kind in the world, home to a variety of endemic plant and bird species. Leaving the levada, we climb to Chão das Feiteiras, where our hike concludes before transferring back to our hotel in Santo da Serra.

We begin along small levadas with a gentle climb into a wide valley. Around mile four, the ascent steepens as we approach Pico do Areeiro, the island’s third-highest peak, reaching the summit near lunchtime—complete with sweeping views and a café for a well-earned break.

From there, we traverse a dramatic volcanic ridgeline of steady ups and downs to the famed “Stairway to Heaven,” a striking series of stone steps suspended above the landscape (not ideal for those with a fear of heights). Continuing along the Vereda do Areeiro, we link the island’s three highest peaks—Pico do Areeiro, Pico das Torres, and Pico Ruivo—passing through volcanic tunnels and climbing steep stone staircases. After reaching Casa de Abrigo do Pico Ruivo, we descend past the “Homem em Pé” rock formation and continue to Achada do Teixeira, our lodge for the night.

In true Madeira fashion, what goes up must come down—and today brings both a significant ascent and descent. We leave our mountain hut and retrace our steps to the trailhead below Pico Ruivo, the highest point in the archipelago. From here, we follow the central mountain range west toward Encumeada.

The trail crosses two protected ecosystems within the Natura 2000 Network: the ancient, lush Laurissilva forest and the dramatic volcanic escarpments of the Central Mountain Massif. Along the way, we pass caves carved into the rock, including Furna da Lapa da Cadela, once used as shelters by locals gathering heather and firewood.

As we approach Encumeada via Vereda da Encumeada, sweeping panoramic views remind you that you’re standing at the very heart of the island.

More climbing today—are you sensing a theme? We begin along Levada do Norte, the island’s second longest levada, crossing two long tunnels (about 1 km each) before leaving the waterway to ascend toward the Pinnacle. It’s a stair-filled climb, rewarded with sweeping views of the valley framed by Pico Ruivo and Pico do Areeiro—an unforgettable lunch spot and moment to reflect on how far we’ve come.

We continue through the ancient Laurisilva forest to Casa do Caramujo, an abandoned mountain home once used as a holiday retreat, near a small winter pond. From there, a final panoramic ascent leads us to the Estanquinhos trailhead. Tonight, we head to the seaside village of Jardim do Mar, our home for the final two nights in Madeira.

Today we continue from Estanquinhos with a full descent—from 5,200 feet all the way to sea level. The trail begins gently before dropping steadily through forested terrain, at times steep and slippery underfoot.

We descend through lush Laurisilva forest, with glimpses over the Chão da Ribeira valley and the offshore islets near Porto Moniz. As we near town, the landscape shifts to orchards, vineyards, and small farms. At last, we arrive in the seaside village of Seixal—completing our cross-island traverse.

After a celebratory swim in Seixal’s cool waters, we transfer back to Jardim do Mar for our final dinner together.

Morning transfer to Funchal for your return flight home.