Madeira Itinerary: A 5-Day Sample Plan and How to Build Your Trip

Quick answer: Five Madeira days: Funchal’s market, Monte toboggans and old town, the Pico do Arieiro–Pico Ruivo ridge, the 25 Fontes levada, the wild west of Porto Moniz and Fanal with Cabo Girão, and the São Lourenço peninsula to finish.

Day 1 — Funchal & Monte

Start in Funchal. Graze the Mercado dos Lavradores — taste custard apples and tiny sweet bananas, but agree prices before sampling exotic fruit — then ride the cable car (about €13–14 one way) up to Monte: the tropical gardens tumble down the hillside (entry about €15), and the descent is Madeira’s oldest thrill ride — the wicker toboggan, two straw-hatted carreiros steering you down the asphalt at 30km/h (about €30–35 for two). Back at sea level, wander Rua de Santa Maria’s painted doors in the old town. Sundowner: poncha — the rum-lemon-honey local rocket fuel — mixed properly with a wooden stirrer.

Day 2 — Pico to Pico Ridge Walk

The island’s greatest walk: Pico do Arieiro to Pico Ruivo (PR1), a ridgeline strung between Madeira’s highest peaks through tunnels and stairways carved into volcanic rock, usually ABOVE a sea of clouds. It’s about 7km one way with serious staircases — arrange a taxi/transfer to start at Arieiro’s observatory at dawn and get collected at Achada do Teixeira (guided or transfer packages roughly €30–60), or simply walk out-and-back as far as the first miradouros if legs protest. Check trail status beforehand; sections occasionally close. Afternoon recovery: the volcanic bowl village of Curral das Freiras far below — chestnut cake and cherry liqueur are the local specialty.

Day 3 — Levada of the 25 Fountains

Levada day. Madeira’s centuries-old irrigation channels come with maintenance paths — now the island’s hiking network. The classic is the Levada das 25 Fontes (PR6, about 9km round trip from Rabaçal; parking/shuttle a few euros): a gentle contour walk through UNESCO-listed laurel forest to a mossy amphitheater where twenty-five springs thread down the rock into a green pool. Combine with the neighboring Risco waterfall spur. Start before 9am — it’s popular for good reason. Dry evening plan: Funchal’s Blandy’s lodge for a Madeira wine tasting flight (from about €10–20), from dry Sercial to raisin-sweet Malvasia — the wine that toasted American independence.

Day 4 — Wild West: Porto Moniz & Fanal

Drive the wild west coast. Morning at Porto Moniz, where black lava corrals form natural swimming pools topped up by the Atlantic (about €3–4 entry; bring water shoes). Climb inland to the Fanal forest plateau — 600-year-old til trees standing in cloud-mist like a fairytale storyboard; if the fog’s in, better still. Southern swing home via Cabo Girão, Europe’s highest sea-cliff skywalk (about €2–3), glass floor 580 meters above the terraces. Fish dinner in Câmara de Lobos, the boat-filled bay Churchill painted — espada (scabbardfish) with banana is the improbable, correct local order.

Day 5 — East: São Lourenço & Santana

East side farewell. Walk the Ponta de São Lourenço peninsula trail (PR8, about 7km round trip) — Madeira with the green switched off: ochre-and-rust cliffs, dragon-back ridges and Atlantic on both sides; start early, carry water, no shade exists. Then the north-coast drive to Santana and its A-frame thatched houses (free to wander; the caretaker village is charming kitsch), pausing at the Guindaste viewpoints. If timing allows, squeeze in Ponta do Sol for the island’s best sunset or a final Funchal pastel de nata crawl. Leave with poncha recipes, calf muscles of iron and firm opinions about levadas — the correct Madeira souvenirs.