A week of family, tunnels and cliffs, surrounded by the immense Atlantic Ocean.
Monday 5 January
I was right to be a little apprehensive about the notoriously bumpy landing at Funchal. The weather is fine and I’m sure it’s all perfectly safe, but the wind shear tosses our humble 737 around like a glider in a storm as we line up to land. I close my eyes, grip K’s hand, and listen hard to Wilco to steady myself. The landing is, naturally, completely routine and I’m left feeling faintly sheepish but much relieved.
It hadn’t occurred to us that the connecting flight from Lisbon would be domestic— we’re through to baggage claim in seconds. Within ten minutes of stepping off the plane, we’re in the arrivals hall greeting Mum, who flew in an hour before us, and piling into a taxi together.
I was last in Funchal 25 years ago. My memories are hazy, but the infrastructure is clearly far more developed than it was. The smooth expressway cuts through multiple tunnels as we sweep across the hillside above town at sunset. Far below, Funchal looks swankier and more polished than I remember it. For perspective, 25 years before my one previous visit, the old authoritarian regime had only just crumbled in the Carnation Revolution. A quarter of a century is a long time.
Ian and Rose are only half hour behind us, and soon we’re all checked in at the Pestana Promenade resort. This is luxury for us: a spacious studio flat with a wide balcony overlooking the sprawling swimming pool. After the winter chill of Granada, Madeira is positively balmy.
The five of us head out for basic groceries before stopping to eat and catch up properly for the first time since we were all together in Krakow for Mum’s 80th last June.

Tuesday 6 January
I wake to discover that the vast expanse of blackness beyond the swimming pool is, of course, the sea. This hadn’t quite registered last night. I just didn’t expect to be this spoiled:

Our first full day in Madeira is low key. Mum, K and I meet up with Ian and Rose at a nearby cafe perched high on a bluff, from where we spot the occasional seal frolicking in the Atlantic below.

After dark, we all saunter thirty minutes into downtown Funchal to soak up the Christmas lights. They’ve been extended by a week—apparently last week’s weather was too ghastly for anyone to enjoy them. The festive season lingers on, but the New Year crowds have gone home and it’s less frantic that it would have been last week.

We end up in a quiet restaurant where none of us are particularly happy with what we’re served. On my plate is a slab of dry, unchewable swordfish. I’m no food snob, but I expect better than this. We wander briefly through the still-bustling Christmas market before hopping on a bus back to the resort. The driver tears through Funchal with the delusion that he’s Lewis Hamilton, taking corners at reckless speeds. The passengers—nearly all fellow reserved Northern European tourists—sit in polite, tight‑lipped silence, each of us clearly thinking the same thing but too well‑mannered to say it.
Wednesday 7 January
We pick up our rental car and drive to the north coast village of Porto de Cruz for a hearty lunch of thick fish soup, spoiled only by my ending up with half a glass of freshly squeezed orange juice in my lap. These things just inexplicably happen.
Driving in Madeira means enjoying the spectacular views in the brief moments when we’re out in the open between the tunnels that plunge though the steep hillsides. They’re relentless. Often we emerge blinking from one only to bolt straight into the next. The longest burrow more than two kilometres through the hills. They’re an impressive feat of engineering, but half the time I feel as if we’re driving at night.
We arrive at a national park on the narrow eastern tip of the island. From the road, a well-trodden hiking trail winds over the hills to the easternmost point. We follow it for as far as mum feels comfortable, then retrace our steps and continue to the tiny port town of Caniçal for afternoon tea and cake.

Another short drive brings us to handsome Santa Cruz, nestled right under the airport runway. The sun is setting—the perfect hour for a stroll along the praia, which ends directly underneath one end of the runway. Here, we find a memorial to the victims of a 1977 plane crash. I later discover that 131 people were killed when, in poor weather and low visibility, a plane touched down 600 metres too far down the runway and slid off the end, plunging 60 metres onto the spot where we’re standing and bursting into flames. A sobering thought, but it explains why the other end of the runway has since been extended out over the Atlantic on hundreds of enormous concrete pillars. (Thankfully, it remains the only fatal accident in the airport’s history.)
Dinner tonight in Santa Cruz is much better than yesterday’s. Ian’s taking over the driving from here, so I order a beer and tuck in. Before heading back to Funchal, we stroll through the small town centre to admire the quirky Christmas decorations that are beginning to feel slightly out of season.

Thursday 8 January
After a full day of exploration yesterday, everyone opts for a slower pace. After lunch, Mum suggests a walk along the levada running above the hotel. Ian and Rose have checked into the hotel spa, so it’s just the three of us.
Somewhere along the way, communication has broken down—K thinks we’re taking a gentle amble to the supermarket and is wearing heavy DMs. Instead, we find ourselves slogging up steep suburban streets in surprisingly strong January sunshine. It’s easy to forget how far south we are—the winter sun here has a real bite to it. K soldiers on gamely, but it’s not the gentle stroll she’d imagined.
Thankfully, once we reach the levada, the path levels out and the walk becomes the relaxed amble K expected. A café at the end serves decent coffee and chocolate fudge cake:

Dinner is at a Singaporean restaurant in town, where we’re attended to by an amicable Scot who spent eleven years in Singapore. We never quite learn how he came to be running a Singaporean restaurant in Portugal, but he’s doing a fine job of it.
We’re supposed to be pub quizzing after our meal, but the local Irish bar has decided to push the quiz back until the Arsenal–Liverpool match finishes. Given that the first half is far from over, it’s unlikely to start before ten. We pivot and wander back to the hotel for a couple of games of Exploding Kittens.
Friday 9 January
We’re all back in the rental car today. First up is a stroll along the quiet Levada Nova a few miles beyond Funchal, with lovely views towards the sea over what is now largely-abandoned agricultural land.


Next, we head to Ponta do Sol for lunch. It’s a tiny place, but parking is a nightmare. It takes nearly an hour of circling and doubling back to squeeze into a spot and decipher the arcane payment system. By the time we sit down to slurp bowls of hearty soup, it’s already mid-afternoon.
After lunch, we soon exhaust the charming but limited sights of Ponta do Sol. Soon, we’re following what was once the main coast road to a waterfall that plummets from the cliffs above, over the road, and down to the Atlantic far below. Last time I was here, this would have been the main road; now it’s a crumbling curio of Madeira’s not-so-distant past.

Finally, we climb steep, winding roads towards the famous 600-metre sea cliff at Cabo Girão. Unfortunately, the top is lost in cloud this afternoon, and there’s little point paying an entrance fee to step out onto the observation deck shrouded in damp, impenetrable mist.
The sun soon returns as the road winds back down to sea level. Back at the resort, there’s a family video call to Sue and Claire in New Zealand before we decamp to an excellent seafood restaurant nearby. The restaurant bills are piling up, but it’s not often the five of us get to eat out together. It’s fine.

Saturday 10 January
It’s Ian and Rose’s final day in Madeira. I handle the driving today: first straight through the centre of the island towards Porto Moniz in the north-west corner. A combination of a hazy memory and the construction of yet more tunnels over the past 25 years means that both the drive and Porto Moniz itself feel very different from what I vaguely recall.

After strolling around the natural lava swimming pools and stopping for lunch, the road climbs a series of steep hairpins. The gradients are no joke and I’m grateful to be driving an automatic. Our next stop is near remote Achadas de Cruz on the west coast, where a cliff towers nearly 500 metres over a narrow strip of agricultural land covered in sugar cane and dotted with tiny shacks. From the top, the view is vertigo-inducing: a sheer plunge to the Atlantic far below:

We cram into a small cable car and make a steep descent to the bottom, where there are stunning views of the remote cliffs of this little-visited corner of Madeira:

Mum’s been coming to the island regularly for 30 years, yet didn’t know this tucked-away spot existed. For the next hour, we potter about absorbing the atmosphere of this primordial spot. Its remoteness and dramatic cliffs remind me of a marginally less barren Iceland.

A few of the two dozen-odd shacks have been repurposed into tiny weekend retreats. One is now a small café, where we sit on the cramped roof terrace sipping hot chocolate and nibbling on piping-hot apple strudel. Without a doubt, this is one of the most stunning spots we’ve visited in all our travels:

Back at the top, the little-used road continues around the western side of the island, full of hairpin turns through deep forest. We barely see another vehicle in this remote corner of the island.
There’s barely time to sit down at the hotel before we’re due at Come Together restaurant, where Mum has booked us in for Saturday night live music. The place is packed and the crowd is decidedly mature—our table appears to be the only one accommodating anyone under the age of 60. In one corner, gold and silver balloons announce one spritely diner’s 91st birthday. Given the demographic, we’re expecting a rousing set of oldies. There’s nothing wrong with that, but when the female singer and her keyboard player eventually appear, they proceed to deliver a gravely unimaginative set of stale standards—Amazing Grace, Imagine, My Way—with all the flair of an office karaoke party. We smile and applaud politely. It’s all part of the Madeira experience.

Sunday 11 January
Sunday begins by delivering Ian and Rose to Madeira airport. It’s been fabulous to do a spot of road-tripping with them—our first since we met up in Greece for Ian’s 50th at the very beginning of our travels two and a half years ago. After dropping them off, Mum navigates me back to Funchal, where we return the rental car and stop for a coffee and a Portuguese egg tart.
We’ve planned the afternoon around the basket toboggan ride down from Monte. An occasionally precipitous bus ride carries us up through Funchal’s hillside suburbs, but we when we reach Monte we find all the toboggans neatly stacked and the boater-hatted tobogganists nowhere in sight. We speculate for a while and conclude it’s probably closed for as long as the nearby cable car is under repair.

With neither cable car nor toboggan run operating, Monte is eerily quiet. Low cloud hangs on the hillside, giving the place a faintly otherworldly feel that reminds me of Malaysia’s Cameron Highlands. Near the deserted cable car station, we find a café and order coffee and cake from the engaging owner, whose English is remarkably idiomatic. I’m curious whether she’s lived in the UK—anyone who uses the word ‘loo’ so naturally must have picked it up somewhere—but before I can ask, we’re accosted by the local drunk.
He’s the only other customer on this quiet Sunday afternoon: a ruddy-faced man in his late sixties with piercing turquoise eyes, nursing a large glass of madeira—clearly not his first of the day. In unsteady, rudimentary English, he attempts to regale us with highlights of his life story. None of us have much idea what these highlights are, but we feign polite interest while doing everything short of semaphore to signal that we’d rather chat among ourselves. The café owner sighs and gives us an apologetic shrug. He’s clearly harmless, just lonely.
We spend our final night in Madeira at one of Mum’s favourite restaurants, where the staff are good enough to bypass their Sunday menu to cook us Portuguese baked chicken, the dish that had caught our eye on the menu in the window. And that’s it. We stop by Mum’s room for a parting shot of whisky and say goodnight.

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