Levadas, cliffs and a canyon of switchbacks
Six days based in one Funchal apartment, two demanding bike days, and a road trip around the wild side of the island. Built from a real visit, not a guidebook.
Settling into Funchal
Where you're staying
Ocean's Glow by Homie, Madeira Acqua Residence, Estrada Monumental: a two-bedroom, two-bathroom apartment in a private residential complex on the western edge of Funchal: doorman, 24-hour security, parking, full kitchen, about 7–10 minutes by car from the old town.
- A grocery store directly across the street makes a cook-at-home night easy
Photos: behomie.com
Getting there
Move Rent-a-Car, a small, friendly local agency, entirely over WhatsApp, with pickup directly in the airport parking lot.
- Ask specifically for an automatic (Funchal's streets are relentlessly hilly) with at least a 1.6L turbo engine, since a 1.2L struggles with four adults and luggage
Today
Settle in, stock the fridge, then a first slow walk through Funchal old town.
- If travelling in late April/May, the annual Flower Festival often has the city dressed in flowers with parades through the centre, worth timing around if dates allow
Dinner
Funchal old town, Rua de Santa Maria: a dense run of small, characterful restaurants; walk until something looks right rather than booking ahead on night one.
Flagship day
Coastal ride to Machico, back through the hills
Day 2
The ride
Happy Bikes, Rua Princesa D. Maria Amélia nº7, Funchal (by the cruise port exit): friendly, well-reviewed, fair prices.
- Out along the coast road toward Machico, then a turn inland onto a genuine effort of a climb, roughly 700m of ascent, before dropping back down into the hills above Funchal on quieter roads, arriving back into the city from above rather than retracing the coast
- One of the best days of the whole trip
Photos: happybikes.pt and Wikimedia Commons (Zarco, Ximonic, Bengt Nyman; public domain / CC)
Lunch
Adega do Pomar, Camacha, worth the detour.
- A rustic Madeiran tavern serving traditional Portuguese cooking; the standout dish is the slow-cooked beef, carved off the bone tableside
- Good enough that we went back a second time
Photos: quintadamoscadinha.com
West & inner island: viewpoints, a church, natural pools
Today
Cabo Girão first thing, one of Europe's highest sea cliffs, with a glass-floor skywalk; go early, parking is limited.
A 580-metre drop
Cabo Girão is one of Europe's highest sea cliffs, falling almost straight down to the Atlantic. The glass-floor skywalk is built right at the edge.
Today
A quick empanada stop at Pastelaria Brava Doce on the way inland, then into the valley for the views, stopping for a local poncha wherever looks good. Capelinha de Nossa Senhora, a small chapel reached by a short flight of steps, then coffee in the genuinely cute town of São Vicente.
A stop worth planning around
Espaço Infinito, Seixal: a small curated viewpoint run by a local, with a grappa tasting at the entrance for a small donation.
Lunch
Lunch at Restaurante Seixal Butcher, a genuine experience: choose your skewer inside the butchery, carry it to the grill yourself, hand it over to be cooked.
- The best chicken skewer either couple has ever had
Afternoon
Porto Moniz for the island's famous natural volcanic-rock pools, then Fanal forest on the way back for an atmospheric walk through laurel forest.
- Just wandering into the forest itself is free; the classified PR13 waymarked trail carries its own separate fee (around €4.50 as of 2026), booked online, and you only need that if you're doing the full official route
Afternoon
Weather note: conditions flipped from sunny to rain within about ten minutes on this leg.
- Pack a light waterproof regardless of the morning forecast
Dinner
Cook at the apartment: the grocery store across the street makes this easy after a long day of driving.
Flagship day
Sea to sky: Pico do Areeiro by bike
Day 4
The ride
Happy Bikes again.
- This is a serious, high-elevation ride for strong, experienced cyclists only
- From sea level up to Pico do Areeiro (1,818m)
- Recommended ascent line: Pernãs → Fonte Santa → Pinheiro → Choupana, which avoids the steepest, most brutal climb directly out of Funchal
- Even so, expect several hundred metres with gradients over 15%
Sea level to 1,818m
Today's ride climbs from the Atlantic to Pico do Areeiro in one push: nearly the full elevation of the island, in a single day, on a bike.
Dinner
Funchal old town, wherever looks appealing after recovering from the climb.
Two coastal hikes: the best of the island on foot
Today
Vereda do Larano, a quiet, little-known cliff walk with incredible views and very few other people on the trail (free at time of writing). Ponta de São Lourenço: a walk along the island's dramatic eastern "dragon's tail" headland, likely the single best hike on the island.
On the classic Pico do Areeiro → Pico Ruivo hike
We'd steer around this one: it's now extremely busy with tour groups.
- If the classic stairway photo is a must, do only the first short section, and go in the late afternoon rather than at sunrise, when it's markedly quieter
On the classic Pico do Areeiro → Pico Ruivo hike
For a similar payoff with far fewer people, Pico Grande has no road access to its trailhead, which alone keeps the crowds away, though the trail beyond roughly the 3.5km mark has been temporarily closed as of early 2026, so its current status needs checking before we build it in.
Last morning in Funchal & departure
This morning
A short, easy walk through banana fields on RB1 Vereda da Ladeira, worth doing on the way past even with limited time.
- A last wander through Funchal old town
- If the Flower Festival is on, the parades are worth timing around
- Check out, return the car via Move Rent-a-Car at the airport, and depart
This morning
Optional: the Cristiano Ronaldo Museum, mostly trophies with limited context, but cheap enough to be worth a quick visit for football fans.
Build this trip
We will start from this one and reshape it around your dates, your group and your pace. Nothing here is a fixed package.
Build this trip See other trips