Five days is the sweet spot for Madeira. It is long enough for the island's three faces – city, mountains and wild coast – plus a spare day for the weather, which a three-day trip never has. The shape: Funchal, the mountain day, a levada, the west coast, then a flexible fifth.
Run it all from one Funchal base, on tours and transfers or with a hire car for the rural days only. The two things to book before you fly are the PR1 trail slot and the sunrise transfer, both of which sell out in spring and autumn. Start with the Madeira tours and tickets that anchor the week.
Before you go: base, season and getting around
Base in Funchal for all five nights. It is central, it is where the tours collect you, and on a five-day trip you lose more to packing and check-ins than you gain from a second base. Swap one night for the north or west coast only if you actively want the drive shortened.
April to June and September to October are the best months: kind walking weather, the island at its greenest, and manageable crowds. You can do everything below without a car, or hire one for the rural days – Madeira's roads are steep and tunnel-heavy, and plenty of first-timers would rather let a guide drive. Sort your airport transfer so Day 1 starts cleanly.
Day 1: Funchal and Monte
The shape: a gentle city day while the flight wears off. Spend the morning in the old town and the Mercado dos Lavradores, then take the cable car up to Monte, €22 return, for the Monte Palace gardens and the view back down over the bay.
Come down on the wicker toboggan, about €30 per sledge for one or two riders, paid in cash on the day. In the afternoon, slot in a Madeira wine tasting in one of the historic lodges near the cathedral, then dinner in the Zona Velha.
Car needed: no. This is deliberately the easiest day of the five, and it keeps the physical days for when you are rested.
Day 2: The mountain day
The shape: your clearest forecast goes here. Do the Pico do Arieiro sunrise and, if you are fit and the trail is open, the PR1 ridge to Pico Ruivo – the island's roof, above a sea of cloud.
PR1 costs €10.50 per person, requires a timed reservation on the SIMplifica portal, and has been one-way only – Pico do Arieiro to Pico Ruivo – since it reopened in April 2026 after nearly two years shut following the 2024 wildfire. It is €7 with an accredited operator, and under-12s are exempt from the fee but still need a slot. A guided transfer drops you before dawn and collects you at the far end, which is the only tidy way to do a one-way ridge without two cars.
Car needed: no, with a transfer. If Day 2 looks grim, swap it with Day 3 or Day 5 – that flexibility is the whole point of five days.
Day 3: A levada walk
The shape: level ground, deep forest, no altitude. Day three is the classic Madeira walk along a levada. The signature route is the Levada das 25 Fontes at Rabaçal, ending at a spring-fed lagoon, with the short Risco waterfall detour worth adding.
If you want something longer and more atmospheric, through tunnels and laurel forest, swap in the Caldeirão Verde instead. Both are classified PR trails, so both need a paid SIMplifica reservation – €4.50 per person, not the €10.50 that PR1 costs.
A moderate half to full day on mostly flat paths, and a deliberate contrast to the ridges of Day 2. It also works when the peaks are clouded in, which is why it sits next to the mountain day rather than far from it.
Day 4: The west coast
The shape: one loop, maximum variety. The west-coast run takes in the Cabo Girão skywalk, the lava pools at Porto Moniz, the black sand at Seixal and the mossy Fanal forest up on the plateau.
A 4WD or jeep tour handles the switchbacks and reroutes around the weather, which is the low-stress way to do this side of the island. Pack a swimsuit even though the day is billed as sightseeing – the Porto Moniz pools are the point for most people.
Day 5: The flexible day
The shape: decide it over breakfast. This is both your best free choice and your buffer for anything cloud pushed out of the schedule earlier in the week.
The strong options: a whale and dolphin trip from Funchal marina; the wild coastal hike at Ponta de São Lourenço, or the fuller east Madeira tour that pairs it with Santana; a dramatic valley half-day at Curral das Freiras; or a beach and pool day at Calheta from the best beaches guide.
Do not over-plan this day. A relaxed finish beats squeezing in one more mountain drive before a flight.
Swap if…
- Bad weather on Day 2: move the mountain to Day 5 and pull the levada or the west coast forward. Nothing else in the week is weather-critical.
- Non-hikers: drop PR1 and visit the Pico do Arieiro viewpoint, five minutes from its car park, then use Day 3 for the gentler Balcões walk.
- With children: the cable car, the toboggan and the boat day carry the week; the 25 Fontes walk is long for small legs.
- No car: the whole plan already runs on tours and transfers from Funchal. See Madeira without a car.
Extending to 7 days
Two more days buy a second coast and a boat day rather than more driving. Add the east – Santana and Ponta de São Lourenço – as its own day, keep a slow midweek day for a sunset catamaran or a food tour, and consider Porto Santo's golden sand for the last day. The full week is in the 7-day Madeira itinerary, and the shorter version is the 3-day itinerary.
Featured image: cudi / Wikimedia Commons / CC BY 2.0
