We begin the crossing with a classic Madeira start: big coastal views and immediate elevation change. Expect a day that feels “real” right away—climbs, descents, and lush green terrain as we work toward Seixal. After the hike, we transfer back to Porto Moniz for the night. (L)

What to expect on trail:

• A challenging opening profile (climb early, legs wake up fast)

• Alternating rugged footpaths and forested sections

• Frequent viewpoints over the Atlantic and the north-coast cliffs

• Approximate distance: 12 miles

Today begins linking the north side into the island’s interior. The scenery becomes more mountainous and the route feels more “cross-island” with longer climbs/descents and changing vegetation. We finish near Senhora do Rosário, then stage for the central crossing with an overnight near Encumeada at Valley View Hotel. (L)

What to expect on trail:

• Sustained ups and downs (pace matters more than speed)

• Cooler air and cloud mist possible as you gain elevation

• A real sense of moving away from the coast and into the backbone of Madeira

• Approximate distance: 11 miles

A highlight day for “Madeira drama.” Encumeada sits in the island’s mountain spine, and today delivers sweeping valley views and that classic feeling of hiking through a living landscape—clouds rolling, light shifting, terrain changing beneath your feet. We finish in the Eira do Serrado area and stay at the Eira do Serrado Hotel, perched above one of the island’s most striking valleys. (L)

What to expect on trail:

• High-country conditions (wind, mist, and fast-changing weather)

• Long scenic stretches where the views just keep opening

• Variable footing—some rocky/stepped sections mixed with smoother trail

• Approximate distance: 11 miles

We start in Curral das Freiras (Nun’s Valley)—a dramatic bowl of mountains—and climb into the high peaks, finishing at Pico do Arieiro. This is the “iconic mountain day”: big effort, big reward. After the hike, we transfer to Funchal for the night to recover comfortably. (L)

What to expect on trail:

• A demanding climb day (steady rhythm, lots of small breaks)

• Cooler temps and wind near the top even if it’s warm below

• High-mountain terrain that feels wildly different from the coast\

• Approximate distance: 14.5 miles

We return to the Pico do Arieiro area to continue the route, then begin the long transition from mountain to sea. The ecosystems shift as you descend—high ridges into greener slopes and eventually coastal landscapes. Overnight in the Porto da Cruz area. (L)

What to expect on trail:

• A descent-heavy day (harder on knees/quads than people expect)

• Big changes in temperature as you drop in elevation

• “Earned” ocean arrival vibes as the coast comes back into view

• Approximate distance: 10 miles

Our final hiking day follows Madeira’s eastern side toward Machico. This is the satisfying finish: coastal views, cliffside drama in places, and the real feeling of completing an island crossing on foot. Celebrate in Machico tonight. (L)



What to expect on trail:

• Scenic coastal traverses with exposure in places (managed carefully, unhurried)

• Tired legs—but high morale and a strong finish-line pull

• A memorable final approach into Machico

• Approximate distance: 10 miles

Group transfer to the airport and flights home.