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Madeira, the island of eternal spring! Want a little preview? We’ll hike Pico Ruivo, swim in the natural pools of Porto Moniz, and try canyoning. In just 8 days, you’ll fall in love with the vibes of the Atlantic garden. Yes.

Is this trip for me?

Party and nightlife
Relax
Nature and adventure
City and cultures
Monuments and history
Physical effort
Trip type
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Itinerary

Madeira in eight days: the island of eternal spring off the coast of Africa, driven end to end by rental car from Funchal. We trek Pico do Areeiro to Pico Ruivo, try canyoning, swim in the lava pools of Porto Moniz and sail at sunset.

Trekking and nature lead, with beaches, the Igreja de Nossa Senhora do Monte, a day on Porto Santo and free afternoons.

A travel route map of Madeira island outlining a circular journey with marked stops and a start-end point.
A WeRoad group trip poses for a photo in front of a traditional A-frame thatched-roof house on a sunny day.

Check-in and first dinner

We check in at the hotel in Funchal, the island's capital, and the trip starts over dinner rather than out on a trail. Hungry yet?

  • Funchal takes its name from the fennel that grows here in abundance, funcho in Portuguese, though our first dinner will thankfully not be built entirely around it.

  • Our first taste of Madeira is more likely fresh fish straight out of the Atlantic, eaten slowly while the group quietly sizes each other up.

A WeRoad group trip in wetsuits and yellow helmets poses for a photo on a rocky hillside under a clear blue sky.

Ready for canyoning?

Adrenalin first thing! A river gorge before any town.

  • Canyoning means descending a river by climbing, swimming, sliding and jumping.

  • With its water-carved gorges, waterfalls and lush vegetation, Madeira is considered the best in the world.

Machico and a sunset miradouro

After lunch and a chance to recover, we take the cars to Machico, Madeira's second largest city.

  • We walk the narrow streets of the town centre down to the seafront promenade, full of cafes.

  • Bolo do caco with a sea view, then sunset from the Francisco Alvares Nobrega Miradouro over Ponta de São Lourenço.

A WeRoad group leader with their back to the camera stands on a rocky mountain peak, making a peace sign over a vast mountain range.

The eternal spring

A dawn start, because the island where it is always spring keeps its very best scenery high above the coast.

  • The hike runs from Pico do Areeiro to Pico Ruivo, about six hours of walking.

  • Boots on early, and we let the views do the talking!

On the roof of Madeira!

Pico Ruivo is the highest mountain on the island at 1862 metres. We hold a steady pace on the trail, fingers crossed for clear weather.

  • One last push to the summit: the overhangs are daunting, but the path is safe and handrailed.

  • A packed lunch, then the same trail back to the cars.

A WeRoad group trip posing on a coastal road under a waterfall cascading from a rocky cliff.

The EU's steepest cable car

Another early start, for the north-western tip of the island.

  • The steepest cable car in the European Union sits at Achadas da Cruz, plunging almost vertically for 450 metres down the dramatic cliff face to sea level.

  • Below it, a different microclimate: unspoilt farmland with small houses and traditional wine presses.

  • The seaside promenade is rated among the island's finest photo spots, and locals sometimes serve drinks at home for a donation. Who could say no?

Porto Moniz, Fanal and Seixal

Via Porto Moniz and its natural lava pools, if time allows, we detour to the Parque Florestal do Fanal.

  • The Fanal is an ancient laurel forest cloaked in thick mist.

  • Then the black-sand beach of Seixal and a plunge into the Atlantic Ocean at a pleasant 20 degrees.

  • The Véu da Noiva waterfall stays in the distance, with a miradouro stop before Funchal.

A hiker with a backpack walks on a stone trail along a high, grassy cliff overlooking the ocean under a blue sky.

Trekking with a view

Hiking in the morning, sailing in the afternoon. Coast or inland?

  • We can reach Ponta de São Lourenço, the easternmost point of the island, on a path over the Atlantic Ocean and red cliffs thick with vegetation.

  • Alternatively we head inland and trek to Levada do Caldeirão Verde, which trades the cliffs and open water for the green middle of the island.

Boat trip at sunset

The afternoon is a three hour boat trip at sunset towards Cabo Girão.

  • We anchor for snorkelling, with equipment on board and a drink for anyone staying dry.

A woman with curly hair sits on a rocky mountaintop surrounded by green shrubs, overlooking a vast mountain valley filled with clouds.

The island from above

South coast day, mostly from viewpoints. Got a head for heights?

  • We start from Câmara de Lobos, which hosted Winston Churchill in 1950, then climb a little towards the vertigo test.

  • Cabo Girão looks over the entire southern coast from a glass platform 580 metres up, the highest ocean cliff in Europe and second in the world.

  • Then the cars again to Ponta do Pargo, the westernmost point of the island, where the view is unrivalled and the sunset worth waiting for.

A woman takes a selfie with a WeRoad group trip on a cliffside overlooking a rocky coastline and the ocean.

Sledding in Madeira?

One last day on Madeira, with a cable car up and something considerably stranger on the way down.

  • The cable car climbs to the Igreja de Nossa Senhora do Monte, the island's most important pilgrimage site, with the view and the botanical gardens too.

  • We come down by sledding, on toboggans first used at the beginning of the 19th century as public transport. Still the most epic descent here!

A tour of the local market

A free afternoon, then the farewell dinner.

  • The Mercado dos Lavradores in central Funchal has the freshest fruit, flowers, intricate crafts and souvenirs.

See you soon, Madeira

Eight days gone, and this is check-out morning in Funchal. Time flies when you are having fun!

  • We check out and say goodbye to an island that has quietly become home.

  • See you soon rather than goodbye: another WeRoad adventure is waiting somewhere down the line.

What's included

What's not included

Roundtrip flight to/from destination
  • Food and beverages when not specified
  • Gas/petrol, parking, toll fees 

  • Trails and trekking entry fees

  • All extras you'll be able to fit in your backpack
  • Anything not mentioned in the "What's included" section

Optional activities

Please note, some extra optional activities will be available for this trip. Your Group Leader will be happy to assist with organizing these activities for the group once the trip starts. Availability may vary depending on location and group preferences.

Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.


  • Teleferica Funchal return trip - approx. USD23

  • Whale watching excursion approx. USD67

  • Surf Lesson - approx. USD65

  • Wine tasting at Quinta do Barbusano - approx. USD20

Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Accommodation

    Hotels, typical guest houses. 

    The first hotel will be shared with you at least 2 days before your departure by your Group Leader!

  • Transport

    Rental car

  • Self-driven tour

    This is a self-driven tour - it isn’t compulsory to drive, however if you are willing to, then please tick the box when booking your trip.

  • Staff

    Our trips are led by a Group Leader who has been specifically trained by us to lead group travels to ensure you have the best time. A WhatsApp group with all travel participants will be created two weeks prior to departure by your Group Leader.

  • Visas and Vaccinations

    Before booking, please ensure to check what documents, visas, and vaccinations are required to enter the country you are visiting. If you have any questions, please contact us.

  • Arrival and Departure Times

    We always advise trying to get to the meet-up point for the first day of your tour by 5pm. On the last day of the tour you are free to leave whenever you want!

  • Luggage

    Backpacks are mandatory to allow easy transfers - we recommend a 45L backpack for our trips.

  • Info on private roomsShow all details

Why WeRoad

  • Small groups, on average 11 people

  • Move or change your trip for free up to 31 days before departure

  • Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed

The Group Leaders

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalFunchal (FNC)
ReturnFunchal (FNC)
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FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Madeira

From
$ 2,028
Book with $ 0
•Free trip change
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