On day 4, choose between coast and countryside. One option begins with a transfer to Ponta de São Lourenco Nature Reserve, where a narrow spine of land runs into the Atlantic. The peninsula loop weaves among ochre cliffs, salt-sprayed grasses and basalt outcrops with sweeping ocean views towards the Desertas Islands and Porto Santo.

Alternatively, join the Levada Nova above the Ribeiro Santa Cruz. This quieter contour reveals farmed terraces and laurel thickets, with sun-dappled waterfalls and birdsong rounding each bend. Both routes showcase different Madeiran moods—windswept volcanic coast or serene irrigation path—yet each preserves the island’s essence: dramatic geology, living agriculture and time marked by the steady hush of water.

On day 5, a transfer to Boa Morte sets you on the Levada do Norte, bordered by pines and eucalyptus and lined in spring with pink belladonna blooms. The path contours above poios terraces, passing kitchen gardens and village lanes where vines drape over stone walls and distant fishing towns brighten the coast below.

Arriving at Cabo Girão Skywalk, gaze down 580 metres to wave-washed fields and the amethyst Atlantic. These are among Europe’s highest sea cliffs; the glass platform heightens the thrill while lending a new angle on Câmara de Lobos and Funchal Bay. Pause to pause for photos and reflection before transferring to your elegant Funchal hotel for a leisurely evening.

On day 7, ride the cable car to Monte from Funchal’s Old Town, drifting above terracotta roofs and the amphitheatre of Funchal towards forested hills. At the top, visit the serene church of Nossa Senhora do Monte and wander pathways of the Monte Palace Tropical Garden, where koi ponds mirror palm fronds and ceramic azulejos tell voyages of Portugal.

Your ticket is included; linger among orchids and cycads, then descend at your own pace, perhaps pausing for a café terrace with harbour views. For those seeking a flourish, the classic wicker toboggan ride back towards town is available as an optional extra, adding a dash of island tradition to a softly scenic morning.

After the gardens on day 7, ride the wicker toboggan from Monte towards Livramento, guided by carreiros in white uniforms and straw boaters. The sledge glides 2 km down polished stone lanes, a smooth, whooshing descent punctuated by laughter and the rhythmic squeak of runners.

This 19th-century tradition once sped locals downhill; today it’s a spirited piece of living heritage and a novel way to see Funchal’s hillside neighbourhoods. This experience is at additional cost and bookable on tour with your local host, subject to weather and queue conditions.

In the late afternoon or evening on day 6, join a guided tasting at Blandy’s Wine Lodge in central Funchal. Explore quiet lodgias stacked with American oak as a specialist explains the canteiro method that ages Madeira under gentle warmth. Compare a tasting flight—Sercial, Verdelho, Bual and Malmsey—while noting aromas of toasted nuts and orange peel.

Founded in 1811, the lodge has supplied toasts from diplomatic salons to Atlantic steamers, and its museum pieces bring the island’s trade history to life. This experience is at additional cost and bookable on tour; purchases can usually be shipped home.

On day 6, indulge in Afternoon Tea at Reid’s Palace, served on the Edwardian veranda overlooking the Bay of Funchal. Tiered stands arrive with finger sandwiches, freshly baked scones and pastries, complemented by passion-fruit jam and island honey, with a curated tea list or a glass of sparkling wine.

Since 1891, Reid’s has welcomed writers and statesmen—Sir Winston Churchill among them—who savoured the same sea-framed ritual. Expect polished service, a smart-casual dress code and the gentle clink of china in the trade winds. This experience is at additional cost and bookable on tour; advance reservation is recommended.

On day 2, a transfer to Parque das Queimadas spares the climb, placing you directly on the Caldeirão Verde Levada. The path threads shady laurel and heather, crossing ravines and slipping through cool levada tunnels as the Vale da Lapa opens towards glimpses of sea and high ridges. The crescendo is the emerald amphitheatre and ribboning waterfall of Caldeirão Verde, its spray drifting across mossy rock.

Levada paths are Madeira’s lifelines, cut by 18th-century water engineers to ferry mountain springs to terraced farms. This section traverses the UNESCO-listed Laurisilva forest, a relic of subtropical woodland once common across Macaronesia. Expect birdsong, damp stone underfoot and the quiet industry of water guiding you back along the contour after lunch, returning by bus or arranged transfer.

On day 3, a minibus to Ribeiro Frio delivers you to the evergreen realm of the Levada do Furado. Follow the channel through ferny gullies and dripping rock where Laurisilva branches knit a cool canopy. Watch for the tiny firecrest and tame finches flitting among laurel and heather as occasional openings reveal white hamlets perched on folds of green.

The levada descends towards the lively square of Santo da Serra, where grills smoke and locals gather for weekend chatter. Sample traditional espetada skewers and rustic bread if you wish, then wander lanes scented with eucalyptus to your historic hotel. This walk layers Madeira’s botany and village life, turning an engineering contour into a portrait of everyday island rhythms.

On day 1, set out from Santana along a panoramic coastal path that joins the ancient cobbled route to São Jorge. Agapanthus and cacti fringe the descent to Calhau, where the ocean breathes against black pebbles and big Atlantic rollers curl under the cliffs. The trail then undulates along cliff bases before climbing to broad balcony views over corniced headlands and the sea.

Above the surf, the São Jorge lighthouse gleams ahead while the pyramidal bulk of Pico Ruivo anchors the horizon. These paths once linked farmers and fishermen between hamlets; today they reveal stone terraces, whitewashed chapels and the island’s rugged north coast. Return to Santana by late afternoon with time to unwind at your hotel before dinner.