Funchal

The levadas are irrigation channels cut across the island to move water from the rainy north to the farmed south, and the maintenance paths beside them are now the finest walking network in the Atlantic islands. Because they follow contours, most are near-level despite crossing dramatic terrain — which means an ordinary walker can spend a day inside ravines and along cliff faces that would otherwise demand climbing. Levada do Caldeirão Verde and the Rabaçal paths are the classics. Take a torch for the tunnels, expect wet feet and vertigo in places, and check whether your chosen route is open after storms.

Madeira's laurisilva is a UNESCO-listed survivor of a forest type that covered southern Europe before the last ice age, and it clothes the wet north and centre of the island in moss, ferns and permanent damp. Walking into it is a distinct pleasure from the coastal paths. Higher still, the volcanic spine offers the island's hardest and most spectacular route, the ridge traverse between Pico do Arieiro and Pico Ruivo, with tunnels and exposed staircases — serious walking that requires a forecast check and an early start, since cloud usually rises by mid-morning.

The city itself repays a slow day. The old town's Rua de Santa Maria carries painted doors along its length, a project that turned a run-down street into an outdoor gallery, and the surrounding lanes hold the fish restaurants. The Mercado dos Lavradores is the covered market, best in the morning, with tropical fruit you will not recognise and a fish hall where the black scabbardfish is laid out looking prehistoric. Along the sea front, the promenade runs west past the marina towards the hotel district and the sea pools.

A cable car climbs from the sea front to Monte, six hundred metres above the city, and the ride is worth it for the view down over the roofs and the harbour. At the top are a tropical garden and a botanical collection. The descent is the famous part: wicker toboggans on wooden runners, steered by two men in white and straw hats who run alongside and brake with their boots, sliding down the public road for a couple of kilometres. It is a genuine local tradition rather than a staged one, and it stops well short of the city — you continue by bus or taxi.

Madeira is one of the great fortified wines and one of the strangest: it is deliberately heated and oxidised in the making, a practice that began when barrels shipped through the tropics improved on the voyage. The result is a wine that is almost indestructible once opened, which is why old bottles survive. The lodges in Funchal run tastings that walk through the styles from dry to sweet, and the ageing rooms under their roofs are part of the tour. Bring an empty corner of your case; this is the island's most portable and most durable souvenir.

Set expectations: Madeira is volcanic and has very little sand. What it has instead is natural sea pools — the lava formations at Porto Moniz on the north-west corner are the best known — and lidos with ladders straight into deep Atlantic water. For actual beach, the neighbouring island of Porto Santo has nine kilometres of it and is reached by ferry in a couple of hours or a short flight, which makes it a comfortable overnight from Funchal. Swimming from the rocks is common but the Atlantic swell deserves respect, particularly on the north coast.

Madeira is a year-round destination and its winter is the point: mild, green, and one of the few places in Europe genuinely comfortable in January, which is why it fills with walkers and cruise passengers then. The critical thing to understand is microclimate. Funchal and the south are markedly drier and sunnier than the north and the high interior, and it is entirely normal for the coast to be in sunshine while cloud sits on the peaks. Check conditions for the specific walk rather than for the island, and be ready to swap a high route for a coastal one.

The airport sits east of Funchal and is famous among pilots for its runway on stilts and its wind, which occasionally diverts flights — worth knowing rather than worrying about. Buses connect the main towns cheaply but infrequently, and the roads are steep, narrow and full of tunnels, so many visitors hire a car and some very sensibly do not. Guided levada walks include transport to trailheads and back, which solves the problem that most good walks are linear rather than circular. Taxis are plentiful in Funchal itself.