Madeira surprises first-time visitors. They expect a gentle island of flowers and mild weather, and they find a vertical world of peaks, cliffs and ancient forest, cut through by water channels and tunnels, with a lively harbour city at its foot. A little planning makes the difference between a trip spent in traffic and queues and one spent walking above the clouds. Here is how to shape a first visit.
How many days
Four full days is a good minimum: one for Funchal and Monte, one for a levada walk, one for the mountains and one for the west or north-west coast. A week lets you add the Cabo Girão cliffs, a boat trip, a lazy day by the pool and a spare day for bad weather, which matters here because cloud can sit on the peaks for a day or two at a time. Many visitors come for ten days or more, especially in winter.
Base yourself in Funchal
For a first visit, the capital is the obvious base. Almost every tour picks up there, the restaurants and the old town are on the doorstep, and the airport is around twenty minutes away. Stay in the centre to walk everywhere, or in the Lido and hotel zone for pools and sea views. Our where to stay guide matches the five hotels on this site to each kind of trip.
What to book ahead
The rules on Madeira’s trails changed in 2025 and 2026. Classified walking routes such as the Levada das 25 Fontes now need registration in a timed slot on the regional SIMplifica portal, with a fee for non-residents over twelve. The famous PR1 from Pico do Arieiro to Pico Ruivo reopened in May 2026 after a long closure, one-way only, with a higher fee and, at first, opening on selected days of the week, so check the current schedule and book early. Guided tours and jeep trips are worth booking a few days ahead in busy periods, and so are wine lodge tours and the famous afternoon tea at Reid’s Palace.
Getting around
In Funchal, walk, but expect hills: the city climbs steeply from the sea. The Monte cable car is both transport and attraction, and the hop-on hop-off bus links the centre with Câmara de Lobos and Cabo Girão. For the rest of the island you have two choices. A hire car gives freedom, and the expressway makes the coasts quick, but mountain roads are narrow and steep and parking at popular trailheads fills early. Without a car, guided tours and jeep trips with hotel pickup are the easiest way to reach the plateaus, Porto Moniz and the trailheads, because public buses to the mountains are limited.
Where the headline sights fit
Day one: Funchal. Explore the Zona Velha and the painted doors of Rua de Santa Maria, the Mercado dos Lavradores and its fruit stalls, then take the cable car to Monte for the Monte Palace Tropical Garden and ride the wicker toboggan down. Finish with a tour and tasting at Blandy’s Wine Lodge. Day two: the levadas. Walk the Levada das 25 Fontes and the Risco waterfall from Rabaçal, starting early. Day three: the mountains. Watch sunrise at Pico do Arieiro and, if you have a booked slot, walk the ridge to Pico Ruivo, or join a guided peaks tour. Day four: the west. Take a jeep tour to the Fanal forest and the lava pools of Porto Moniz, or the south-west villages and a distillery, with Cabo Girão on the way.
Rainy-day plans
Weather on Madeira is local: if it rains in the north, the south is often dry. When it does pour, head indoors to Blandy’s, the 3D Fun Art Museum, the CR7 Museum or the covered market, or ride the hop-on hop-off bus with the roof over your head on the lower deck.
Seasons
Madeira is a year-round destination. Spring brings flowers and the Flower Festival, summer is warmest and busiest, and autumn is still warm with fewer crowds. In November and winter, Funchal stays mild, but the mountains are cold and often wet, trails can close after storms and the days are short, so plan hikes for the morning and keep a backup day. The Christmas lights and New Year’s Eve fireworks are famous and fill hotels well in advance.
Money and manners
Cards are accepted almost everywhere, but carry some cash for small cafés, market stalls and the toboggans. Bring proper walking shoes and layers for the mountains, and a swimsuit for the lava pools. Try espetada, black scabbard fish, bolo do caco bread and a glass of Madeira wine, and leave room for the fruit at the market.
