A week is a luxury: four PR trails in four different landscapes, a dolphin and whale cruise with the Monte toboggans in the afternoon, foggy Fanal with the Porto Moniz pools and a morning of adrenaline in a canyon. Every day has a backup option, and days can be shuffled to follow the weather.
The ridge above the clouds: PR 1 from Pico do Areeiro
The most spectacular day of the stay. You start from the Pico do Areeiro car park and walk the ridge towards Pico Ruivo, between cliffs and a sea of clouds. Leave as early as you can: in season the car park fills before dawn, and mornings tend to have the best visibility.
The crossing costs €10.50 and requires a SIMplifica booking, and a one-way system applies beyond Pedra Rija. The ridge is far windier than the valley, so a windproof jacket earns its place even in summer.
Closures are announced from one day to the next: check the trail status on its page in the morning.
Practical: About 40 minutes by car from Funchal. The summit car park takes cards only; there is a cheaper car park a little lower down.
Bad-weather alternative: If the summit sits in cloud: PR 11 Vereda dos Balcões from Ribeiro Frio, short and easy, with a viewpoint that still works in poorer visibility.
Day 2
Water and laurel forest: PR 6 Levada das 25 Fontes
The Rabaçal classic: the levada leads to a rock bowl where twenty-five springs surface. A one-way system is sometimes in force, and the return then follows a bypass variant. The shorter option from the same car park is PR 6.1 Levada do Risco.
Bring a head torch, because some variants pass through unlit tunnels. Stones near the water stay slippery long after rain.
Closures are announced from one day to the next: check the trail status on its page in the morning.
Practical: Drive the ER 221 up to the Paul da Serra plateau; on the long descent brake with the engine in a low gear.
Bad-weather alternative: If rain floods the west: PR 9 Levada do Caldeirão Verde in the north, or the free Levada Nova in Ponta do Sol.
Day 3
Ocean and Monte: dolphins in the morning, the wicker toboggan in the afternoon
Madeira is one of Europe's better places to watch cetaceans: dolphins are seen year round, and the whale species change with the season. Most cruises leave from the Funchal marina, some from Calheta; morning departures usually get calmer seas.
After the cruise, stay in Funchal and take the cable car from the old town up to Monte. The Monte Palace tropical garden comfortably fills two hours, and below the church the famous wicker toboggans set off: two carreiros in white uniforms and straw hats steer you down the tarmac to Livramento, halfway down the hill. From there, get back to the centre by bus, by taxi or downhill on foot.
Practical: A cruise usually takes 2 to 3 hours; book ahead in season, and bring something for seasickness if you are prone to it. The toboggans run Monday to Saturday and tickets are sold on the spot only (€30 solo, €40 for two); a one-way cable car ticket is enough.
Bad-weather alternative: In rough seas operators cancel and refund; try to move the cruise to another morning. Monte itself works even in drizzle, and the gap left by the boat is easily filled by the fishing town of Câmara de Lobos and the Cabo Girão cliff with its glass platform about 580 m above the ocean.
A levada carved into the slopes above a valley, four tunnels and a waterfall dropping into a green cauldron. It starts at the Queimadas forest park; the route is flat but long, and a torch is mandatory.
After the walk, stay in the north: Santana is famous for its thatched houses, and the coast near São Jorge for wild cliffs.
Closures are announced from one day to the next: check the trail status on its page in the morning.
Practical: A SIMplifica booking is required, as on every PR. The Queimadas car park fills by midday, so arrive in the morning.
Bad-weather alternative: This day itself often serves as the backup for the west. If the whole north is rainy, fall back to a city day in Funchal.
Day 5
Fog and laurels: Fanal and the north-west
Fanal is a piece of UNESCO-listed laurel forest, famous for photos of trees in the fog. Here a cloud does not ruin the day, it makes it. Choose PR 13 Vereda do Fanal or the gentler PR 14 Levada dos Cedros.
In the afternoon drop to the coast: the natural lava pools of Porto Moniz and the cliff road near Seixal.
Closures are announced from one day to the next: check the trail status on its page in the morning.
Practical: The plateau gets cold and wet even in summer, so pack a rain jacket. The descent to Porto Moniz is winding; brake with the engine.
Bad-weather alternative: Fanal is at its best in cloud. In a real downpour: the São Vicente valley and the quiet north coast.
Day 6
Adrenaline in the gorge: canyoning for beginners
Madeira has dozens of canyons, and operators run trips for complete beginners: rope descents beside waterfalls, natural rock slides and jumps into plunge pools. Wetsuit, helmet and harness are included, and a level-one canyon asks for nothing beyond ordinary fitness.
Popular beginner canyons sit in the northern valleys, including some near Seixal. On the way back south over the Encumeada pass, stop at Taberna da Poncha in Serra de Água: a classic stop for a poncha and a snack rather than a full meal.
Practical: Book ahead and choose only licensed operators with a guide.
Bad-weather alternative: After heavy rain operators cancel because water levels spike; that is normal and speaks well of them. Instead: museums and Madeira wine lodges in Funchal.
A completely different Madeira: a treeless peninsula, red rock and ocean on both sides. The best pick when the mountains drown in cloud, because the eastern tip keeps its own, drier weather.
There is no shade and no water on the route, so go in the morning or late afternoon and carry more water than usual. In strong gusts the walk turns unpleasant; check the forecast before driving out.
Closures are announced from one day to the next: check the trail status on its page in the morning.
Practical: The trailhead at Baía d'Abra beyond Caniçal sits minutes from the airport, which makes this a natural last day.
Bad-weather alternative: In a gale: PR 10 Levada do Furado from Ribeiro Frio, sheltered by forest.
Plan add-ons: for a spare half-day
An evening after a shorter trail or a morning before the flight has room for more than the schedule suggests. These ideas need no reshuffling of days.
Cable cars
The Funchal to Monte cable car is a first-day classic, and the small cable car at Achadas da Cruz in the north-west, reputedly among Europe's steepest, drops to ocean-side fields cut off from the world.
Catamarans along the south coast, under the Cabo Girão cliff, some with an ocean swim stop. A good pick for a day off your feet; evening departures catch the sunset.
Forest tracks and mud in the east of the island, in a guided group. Dress to get wet and dirty, because that is part of the fun; a driving licence is usually required for the driver.
This plan is indicative. Trail statuses, weather and cruise availability change from one day to the next: before each day, check the trail status in our catalogue and the forecast for the region. Fees and booking rules per SIMplifica.