From sultry seaside to misty jungle: Exploring Portugal's wild frontier

I'm walking a long, lonely road edging a 600-metre ridge looking for a drink. In late afternoon, the sun hangs just above the craggy peaks, casting uneven shadows on muddy-green hillsides that stretch into the misty distance. The air is close and so still I perceive an audible swoosh from a soaring falcon. Yet my mind echoes with the whistling theme from The Good, the Bad and the Ugly. My gritty footsteps scratch out a beat while lizards scuttle to the margins.

At Serra de Agua, a village submerged in laurel and eucalyptus, two leathery ranchers stand outside Tasquinha da Poncha, hand-rolled cigarettes smouldering between their lips. A bar. I hesitate, approach, glance toward them and nod. They exhale sedately and flick their chins north. " Olà," they croak.

Madeira, counter to the beachy, package-tour image of the Portuguese satellite island, is not without its drama. Yet, no matter how violently the frothy waves batter the shore, no matter how exquisite the silhouettes of olive-skinned boys diving off the rock face, they will be outperformed by the wild-frontier landscape inland, the smoky sea panoramas framed by jagged, jungly layers of green.

Like so many visitors to Madeira, I was dispatched to the sybaritic seaside: the sultry capital, Funchal, the tawny southern beaches, the coastal lookouts and rock pools. Only by extending my stay and venturing beyond the obvious did I genuinely warm up to the place.

But here's the thing: It's not for everybody. First of all, to explore Madeira à la carte, you need wheels. Finding no affordable automatic vehicles on the entire island – without which I am, admittedly, useless – I balked at hiring a car. This turned out to be a blessing.

Spotting a taxi rank outside a Sixt car-rental outlet in Funchal, I ask the front driver if he'd take me to my mountainside hotel via the scenic route. For less than $100 (below Sixt's daily rental fee), Paolo handles the task with gusto. For four hours we wind our way up hillsides, dodge motorcycles, pull up precariously on precipices and generally test the resilience of my stomach. Alone at the wheel I would be toast.

At sea level, we plow through plantations of bananas ripened by the thick, sweltering air. You won't have tasted Madeiran bananas. "They're short and fat, below EU standard size," Paolo says, with a flick of his hand. Despite being sweet as Chiquitas and, for some, handily kid-sized, they're exported only to mainland Portugal. It's enough to give a small island a complex, but Paolo isn't letting on.

Any arable land at 300 metres to 900 metres above sea level, where the air is fresher, belongs to winemaking. North of that and you're into the sour-cherry groves, the source of Portugal's obscure, bitter spirit, ginja. Vineyards bleed westward from Funchal to supply Madeira winemakers such as Blandy's, which owns some 450 acres. "Our island has two religions," Paolo tells me. "Catholics and alcoholics."

Madeira's position on the caravel route to Brazil meant the ships stocked up here. And when the colonists' wine kept going off over the long, hot journey, Madeirans doubled down, concocting a fortified digestive wine that would keep for, it turned out, centuries.

Most Madeiran wineries do business out of Funchal, but Vinhos Barbeito, a 60-year-old boutique vineyard, operates a free tasting room in the cool, damp hills, and Paolo snakes around a yawning gorge to take me there. Amid the groaning shelves and antique barrel tables, the heavy, fermented air is enough to get you drunk; Paolo steers me to the bar anyway. At $300 a bottle, his personal favourite, Barbeito's 1978 Sercial Frasqueira, is off the table, but there's a 10-year-old dry reserve to taste. A server sidles up and pours us a finger each, nodding to the spit bucket, but we find it too irresistibly velvety and smooth not to gulp it down.

Lolling out the open window as we putter down to Camara de Lobos, I can almost touch the vines. At a pointed white church in the village square, I jump out for a view of the rippling vineyards, straight out to sea. A few minutes before 4 p.m., locals shuffle in past the palm trees for services and soon a choir of young voices lead them in a hymn, all the evidence you might need that God exists.

From here, Paolo feels duty-bound to wend down toward Ribeira Brava. The cobblestone resort town is blessed with a calm seafront and an enchanting Baroque church bookended by cliffs, but between the concrete hotels and chain bakeries, there's not much to do except dodge Venezuelan tourists on the promenade. So, after a short wander, we blow out of town on skinny roads laced with orange bougainvillea and meander through fields of sugar cane half a millenia old.

Straddling Madeira's central valley, the sugar-cane plantations around Ribeira Brava served as proto-incubators for sugar production and the devastating slave trade that propped it up. Prince Henry the Navigator established the crop to make the island profitable and eventually Madeira grew into the world's leading producer. When Portugal moved production to Brazil in the 1500s, most farmers reinvented themselves.

But a few stayed in sugar, which is what draws me to Tasquinha da Poncha in the mountain village of Serra de Agua, after Paolo drops me at my guesthouse.

Madeirans process their small sugar-cane crop into a sweet distilled liquor called aguardente de cana, then mix it with fresh citrus and honey into a cocktail called poncha. You can order it in most bars or you can climb the island's central spine to the poncha heartland.

Tasquinha da Poncha is barely 15 kilometres from the sugar-cane fields, but so isolated there might as well be tumbleweed bowling down the rural road. So I'm surprised when I swing open the door to a room buzzing with workers, families, little old ladies, all picking through free bowls of peanuts with their happy-hour goblets. As the handsome young bartender muddles lemons, I perch nearby and survey shelves of gum and Kinder eggs, the pool table and pinging arcade games – less saloon than glorified general store.

Poncha socks you with a sour, bitter, saccharine punch. If I still had my wits about me after the first one, I'd abandon it for something less obvious. Instead, encouraged by soccer on the TV and an obliging bartender, I order another hit. Eventually the pinging swirls together with the roar of soccer fans and general swelling of chatter as the alcohol takes hold of the room. I should have eaten more peanuts.

In the morning, to get as far away from poncha as possible, I hike in the opposite direction to the height of the Encumeada Valley. Steps up into the woods mark the start of the Caminho do Pináculo e Folhadal, a path along one of the island's 16th-century aqueducts – levadas, in Portuguese. Levadas are more plentiful than highways in Madeira, gently guiding rainwater over hills and through laurel forest to more parched areas. With a pack of water and pastries from my guesthouse, I turn left and pad toward Bica da Cana, sticking close to a couple who've wisely brought a flashlight as we creep through a mountain tunnel. At 1,500 metres, the breaks in the trees reveal views over grand gorges, before we're swallowed again by jungle and sprayed by rushing waterfalls.

The entire trail would take a full day, but I've called Paolo to collect me a few miles in, on a hill coated with wild parsley and oregano. He gets out to stretch his legs and through a wind farm we can see to both coasts, a spectrum of blues and greens. Some of the bay trees up here, Paolo says, are older than the discovery of Madeira itself, six centuries ago.

Back in the car, he drives me east past Pico Ruivo, the island's highest peak at 1,862 metres, with its own, more strenuous levada walks. We detour along the coastal route, through the town of Sao Jorge, and explore a lesser-known levada called Rei, which runs flat and easy through rainforest to a historic mill.

Following the channel of gently trickling spring water, I pass two, maybe three groups in an hour. Granted, it's a weekday. Madeira's levadas aren't exactly virgin ground. But nor are they anything like the groove-worn boardwalks by the sea, with their whiff of idling tour buses. Up here, you feel as if you can literally walk off into the sunset. That's my kind of drama.

Your turn

Where to stay

Dorisol Pousada dos Vinhaticos: Serra De Agua, pousadadosvinhaticos.com; doubles from $116, breakfast included.

This remote log cabin is decorated with dark-wood antiques and handmade textiles – but not so fashionably as to detract from the views. Every window looks out onto the Encumeada Valley, known as Portugal's Grand Canyon, and the outdoor terrace cantilevers over a wooded gorge.

Quinta das Eiras: Santo Antonio da Serra, madeiravive.com; doubles from $98.

One of few resorts in Madeira's less-travelled east, this quinta has a slightly more luxurious set-up, with standalone cabins, eat-in kitchens and an outdoor pool, though the closest restaurant is five minutes away by car. Some spectacular, secluded walks scale the surrounding hills.

Where to eat

Restaurante Santo Antonio: Estrada João Gonçalves Zarco, Estreito De Camara, restaurantesantoantonio.com.

Espetada is the national barbecue and Santo Antonio, above, is the national favourite, serving skewered meats with salty garlic potatoes and fried cornbread cubes called milho frito.

Restaurante Puro Lusitano: Caminho dos Pretos, facebook.com/restaurantepurolusitano.

This old ranch house in the hills above Funchal specializes in meaty stews and grilled fish, served on sharing platters with chunky roasted potatoes, tomatoes and olives. In the off-season, call ahead for a table by the fire. Or come on a weekend, for the live folk music.