Madeira

Funchal, the capital, is home to roughly 100,000 of the archipelago's 250,000 people and climbs the hillside in an amphitheatre around its bay. The Mercado dos Lavradores opened in 1940 in the monumental style of the Estado Novo regime; its tiled façade and flower-sellers in striped folk costume are as much a sight as the passion fruit, custard apples and black scabbardfish on the stalls inside. A few streets away, Funchal Cathedral (the Sé) is one of the oldest buildings on the island, finished in the early 1500s with a cedar ceiling in Moorish-influenced style, while the yellow-walled Forte de São Tiago has guarded the seafront since the 17th century. The surrounding lanes of the Zona Velha are painted-door country by day and poncha-bar country by night.

The Teleférico do Funchal lifts you in about twenty minutes from the old town to the hillside parish of Monte, 560 metres above the harbour. Up here, the Jardim Monte Palace Madeira spreads oriental gardens, azulejo panels and koi ponds across a former hotel estate, and the church of Nossa Senhora do Monte holds the tomb of Charles I, the last Austrian emperor, who died in exile on the island in 1922. Then there is the descent. The Associação dos Carreiros do Monte runs the wicker toboggans that locals used as public transport from the early 19th century: two drivers in white, rubber-soled boots as brakes, two kilometres of steep asphalt at speeds that have been clocked near 40 km/h. The audio guide tells you the history before you climb in — the ride itself leaves no time to listen.

The island's spine is a line of volcanic peaks that regularly stand above a sea of cloud. Pico do Arieiro (1,818 m) is reachable by road and is the classic sunrise spot; from its summit the PR1 Vereda do Areeiro trail runs along knife-edge ridges and through hand-cut tunnels to Pico Ruivo, at 1,862 metres the highest point in Madeira. It is one of Europe's great mountain walks, around seven kilometres each way with serious ascents, so most people start early and watch the weather. The guides at each end explain how this landscape formed — the last eruptions were only about 6,500 years ago — and why the plants clinging to the rock exist nowhere else.

Madeira's north is wet and its south is dry, so from the 15th century settlers carved narrow stone channels — levadas — to carry water across the island. More than 2,000 kilometres of them were built, and their maintenance paths now make the best walking trails anywhere in the Atlantic. The PR6 25 Fontes hike & Levada do Risco above Rabaçal leads to a mossy amphitheatre fed by twenty-five springs and a veil of a waterfall; the Levada do Caldeirão Verde PR9 near Santana threads tunnels and cliff ledges to a green cauldron of a cascade. Both run through the laurisilva, the subtropical laurel forest that once covered southern Europe and has been a UNESCO World Heritage Site since 1999. For the forest at its most atmospheric, go to Fanal Forest on the Paul da Serra plateau, where ancient, wind-bent til trees stand in the fog like something from a fable.

West of Funchal the coast road climbs to Cabo Girão, a sea cliff of around 580 metres with a glass-floored skywalk hanging over the terraced fajãs far below. In its shadow sits Câmara de Lobos, the fishing village where Winston Churchill set up his easel in 1950 and where the scabbardfish boats still come in under the cliffs; it is the home of poncha, the island's rum-and-citrus cocktail. Back in the capital, Blandy's Wine Lodge has been run by the same family for two centuries and walks you through the sugar-to-vineyards story of Madeira wine — the fortified wine that was heated in ships' holds on the way to the colonies and toasted at the signing of the American Declaration of Independence.

The north coast is a different island: basalt, surf and waterfalls that fall straight onto the road. At Piscinas Naturais do Porto Moniz, lava flows have cooled into natural seawater pools that the Atlantic refills with every wave. Inland at Santana, the triangular thatched palheiros — once family homes with the harvest stored in the loft — survive as the island's most photographed houses, in a municipality that UNESCO named a biosphere reserve in 2011. At the opposite end, Ponta de São Lourenço is Madeira stripped bare: a treeless volcanic peninsula of red and ochre rock, where a nature-reserve trail from Caniçal walks you out to the end of the island with the ocean on both sides.

Funchal is compact and walkable, and its cable car, buses and the toboggan cover Monte. For the peaks, the levadas and the north coast you will want a hire car or a tour; roads are excellent but steep, and the tunnels that now bore through the mountains have cut most cross-island journeys to under an hour. Weather changes by valley — sun in Funchal, cloud at Arieiro, rain in Santana — so check the summit webcams before you commit to a hike. The audio guides work offline on the trail, where signal does not.