A Winter Sun Week in Madeira: Funchal to Calheta

Why Stay South and Low in Winter

Madeira in winter is really three climates on one island, not one. Head up to Pico do Arieiro and it can be close to 0°C at dawn; drive to the north coast around Porto Moniz and you’re likely under cloud and drizzle; stay on the south-facing strip between Funchal and Calheta and you’re commonly sitting at 19-21°C in short sleeves. This itinerary is built entirely around that third option. It deliberately keeps you at sea level and on the sunnier south coast for all seven days, trading the levada walks and mountain sunrises of a hiking-focused week for gardens, old-town streets, sheltered beaches and boat trips that work regardless of what the clouds are doing over the peaks.

That means Porto Moniz, Santana and Pico do Arieiro are off the plan on purpose, not by oversight — they belong to the wetter north and the cold high ground, and a winter week has no business up there. If mountains and levadas are what you’re after, our Madeira Hiking Week covers that ground properly; this one doesn’t try to do both.

Day 1: Arrive and Settle into Funchal

Land at Madeira Airport in Santa Cruz and transfer into Funchal, the island’s capital and the base for this whole week. Funchal’s harbourside position gives it the mildest, most sheltered climate on the island, which is exactly why it anchors a winter-sun itinerary rather than a base further inland.

Spend the afternoon easing in around the Funchal Old Town, with its lanes of painted doors, before an early dinner. If jet lag or a late flight has cost you the day, that’s fine — this itinerary has no fixed timings on day one beyond arriving and getting oriented.

Day 2: Funchal City and the Hills Above It

A full day in and around the capital. Start at the Mercado dos Lavradores, the 1940s Art Deco market where the fish hall’s slabs of black scabbardfish sit below floors of tropical fruit — worth a look even if you’re not buying, though be wary of the fruit-tasting stalls that bill by weight afterwards.

From there, take the cable car up to Monte, a short rise above the city rather than a mountain excursion, for the gardens and the view back down over Funchal Bay. Coming back down, the wicker toboggan is a novelty ride, not transport — it stops partway at Livramento, so you’ll still need a taxi or bus back into town.

Round off the day with a guided walk through the city: a guided walking tour through Funchal with local food and wine tastings along the way is a relaxed way to cover the old town’s history without having to research it yourself.

Day 3: Camara de Lobos and Cabo Girao

Head west along the coast to Camara de Lobos, the fishing village where Winston Churchill used to paint, and still the best place on the island for a proper poncha in a harbourside bar.

A short drive further on is Cabo Girao, one of Europe’s highest sea cliffs at around 580m, with a free glass-floored skywalk over the drop. It’s a striking stop, and — unlike the mountain peaks this itinerary avoids — it’s a five-minute look rather than a climb, so it fits a low-key winter day without any altitude concerns.

Return to Funchal for the evening, or, for a change of pace, spend the afternoon on the water: a guided walk through Funchal’s ecological park is a gentler, shorter alternative if you’d rather stay closer to green space than cliffs today.

Day 4: West to Calheta and Ponta do Sol

Today the route pushes further west, into the sunniest, driest corner of the south coast. First stop is Ponta do Sol, a steep-sided village that claims the most hours of sunshine on the island — its name means literally “point of the sun,” and in winter that reputation earns its keep.

Continue to Calheta and its imported golden-sand beach, the Calheta Beach, Madeira’s answer to a proper swimmable bay rather than the black volcanic shingle found elsewhere. It’s worth knowing the sand was brought in from Morocco rather than natural to the coastline — it doesn’t make the beach any less pleasant, but it’s not the wild Atlantic look some visitors expect.

For an afternoon on the water, a private charter aboard the Aestus luxury boat out of Calheta gives a warmer, calmer alternative to the choppier waters further east, with views back at the cliffs of the west coast from sea level.

Day 5: Madalena do Mar, Jardim do Mar and an Optional Waterfall Walk

Continue exploring the far west at an easy pace: Madalena do Mar and Jardim do Mar are small, quiet villages squeezed between cliff and sea, both worth an hour of wandering and a coffee rather than a full day’s plan. Paul do Mar at the western edge is Madeira’s main surf spot, interesting to watch even if you’re not paddling out.

If you want one proper walk this week without heading north or gaining serious altitude, this is the day for it. The 25 Fontes and Risco waterfalls sit inland from Calheta at Rabacal, reached by a shuttle from the car park since the access road is closed to private cars. It’s a genuine levada walk with a real trail-access fee attached — official Madeira trails have been paid, reservable routes since August 2021, so don’t expect to just turn up.

a guided tour to the 25 Fontes and Risco waterfalls from Calheta handles the logistics, permits and shuttle in one booking, which is the easiest way to fit this walk into an otherwise low-key week. If you’d rather skip walking altogether, simply spend a second day around Calheta’s beach and villages instead — nothing else in this itinerary depends on it.

Day 6: East to Machico and Ponta de São Lourenço

Cross back through Funchal and continue east to Machico, the site of Madeira’s first landing in 1419 and now home to another imported golden-sand beach — like Calheta’s, brought in rather than natural, and worth mentioning before anyone pictures a wild cove.

From Machico, the Ponta de São Lourenço peninsula is the island’s driest, most exposed landscape: bare red-and-ochre cliffs with no shade at all, which in practice makes it a good winter walk when the sun is welcome rather than something to escape. a guided hiking tour out to the eastern cape at Ponta de São Lourenço is the easiest way to do it without worrying about wind, timing or the lack of any shelter along the way.

On the way back, Santa Cruz near the airport and Canico both make an easy coffee stop before returning to Funchal for the evening.

Day 7: Funchal, at Leisure, and Departure

A last day with no fixed plan. Revisit whatever caught your eye earlier in the week — the market, the old town’s restaurants, a wine tasting — or simply sit by the marina with the sea at a comfortable 19-20°C even in January. If your flight is in the afternoon, that’s easily enough time for one more coffee in the old town before heading to the airport.

Planning This Week

	South coast (this route)	North coast	High peaks
Typical winter daytime temperature	19-21°C	Several degrees cooler, often cloudy	Near or below 0°C at dawn
Rainfall in winter	Lowest on the island	Highest on the island	Frequent, sometimes snow
What this itinerary covers	All 7 days	Not included	Not included
Day	Focus	Optional guided activity
1	Arrival, Funchal	—
2	Funchal, Monte	Funchal walking tour with tastings
3	Camara de Lobos, Cabo Girao	Ecological park guided hike
4	Ponta do Sol, Calheta	Aestus private boat charter
5	West coast villages	25 Fontes and Risco guided tour
6	Machico, Ponta de São Lourenço	Eastern cape guided hike
7	Funchal, departure	—

A car makes this route considerably easier, since the VR1 expressway keeps Funchal-Calheta and Funchal-Machico both under an hour despite the distance. Without one, base in Funchal and use day tours for the west coast and the eastern cape — see our guide on getting around without a car for the realistic options. For the wider seasonal picture behind this route, Madeira in Winter and north versus south Madeira both go deeper into why the coasts behave so differently at this time of year.

Madeira Winter Sun Week: Your Questions Answered

How warm is Madeira in winter, really?

There isn’t one answer, and that’s the point of this itinerary. The south coast around Funchal and Calheta usually sits at 19-21°C by day in December and January, with the Atlantic around 19-20°C. The north coast runs several degrees cooler and wetter, and the mountain peaks above 1,500m can be close to freezing on the same afternoon.

Do I need a hire car for this route?

It helps considerably. The VR1 expressway links Funchal to Calheta and Machico quickly through tunnels, and a car lets you set your own pace between beaches and villages. It isn’t essential if you’re happy to base yourself in Funchal and take day tours for the west and east coast.

Is this itinerary suitable if I don’t want to hike?

Yes. Every day here can be done as a walk-and-sightsee day rather than a proper hike. The one optional trail, the 25 Fontes and Risco waterfalls, is offered as a guided tour and can be skipped entirely without breaking the route.

Why does this itinerary skip Porto Moniz, Santana and Pico do Arieiro?

Those three sit on the wetter north coast or up at altitude, exactly where this winter-sun format is designed to avoid. If you want them, they belong on a different week; see our full hiking-focused itinerary instead.

Are the beaches at Calheta and Machico natural?

No, and it’s worth knowing before you go. Both are imported golden sand laid over the natural volcanic shingle, which is why they’re calm, shallow and good for swimming rather than a wild Atlantic beach experience.

What’s the best month within winter for this itinerary?

December through February all work, though December is markedly busier and pricier around the New Year fireworks in Funchal. January and February give the same south-coast temperatures with easier availability and lower hotel rates.

Will it rain on the south coast in winter?

Less than you’d expect, but not never. Funchal and Calheta are in the island’s rain shadow, so dry, sunny spells are the norm; a wet day is more likely to be a reason to explore Funchal’s markets and wine lodges than to cancel plans outright.