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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.

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Party and nightlife
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Nature and adventure
City and cultures
Monuments and history
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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 WeRoad group trip poses for a photo in front of a traditional A-frame thatched-roof house on a sunny day.

Check-in

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

  • 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. We swap the calm of arrival day for a river gorge, and only later get anywhere near a 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

  • After lunch and a chance to recover, we take the cars to Machico, Madeira's second largest city, and walk the narrow streets of the town centre.

  • The seafront promenade is full of cafes, so 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 is Pico do Areeiro to Pico Ruivo, about six hours of walking, so 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, and we hold a steady pace on the trail, fingers crossed for clear weather.

  • One last push to the summit, overhangs daunting but the path safe and handrailed, then a packed lunch and the same trail back to the cars.

 

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

Achadas da Cruz

Another early start, this time for the north-western tip of the island, where the way down to sea level is not a road.

  • 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, a seaside promenade rated among the island's finest photo spots, and locals who sometimes serve drinks at home for a donation.

 

Porto Moniz

  • Via Porto Moniz and its natural lava pools, if time allows, we detour to the Parque Florestal do Fanal, 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, with the Véu da Noiva waterfall distant and 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 and sailing in the afternoon, and today the walking part of it comes with a genuine choice.

  • 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, anchoring for snorkelling, equipment on board, 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 done from viewpoints, and it finishes right out at the far western end of the island.

  • We start from Câmara de Lobos, which hosted Winston Churchill in 1950, then climb a little towards the viewpoint that puts vertigo properly to the 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, and it involves 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

  • The free afternoon points to the Mercado dos Lavradores in central Funchal for the freshest fruit, flowers, intricate crafts and souvenirs, then the farewell dinner.

 

Check out

Eight days gone, and this is check-out morning in Funchal. Time flies when you are having fun, which is the problem with it.

  • We check out, sort the bags and say goodbye to an island that has quietly become home over the course of these last eight days.

  • Then it is see you soon rather than goodbye, because everyone standing here already knows that 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
Our customers sayExcellent
4.8 out of 5 based on 601 reviews
Overall, a great trip and a fantastic way to experience Madeira. We had a really good group, which made the whole experience even better. We stayed in the same accommodation throughout the trip. The rooms were fairly basic, but the hotel had two large outdoor pools and the breakfast was good, so it worked well as a base for exploring the island. The included activities, especially the canyoning, boat trip and hikes, were all great experiences and gave us the chance to see some of the best parts of Madeira. As a group, we also decided to add sea kayaking and go-karting, both of which were brilliant and I’d definitely recommend WeRoad consider adding these as optional activities to future Madeira trips. Our Group Leader had clearly done a lot of research before the trip and took us to all the main tourist spots, as well as some great places we probably wouldn’t have found ourselves. Whenever the group decided to do additional activities, he organised everything straight away and made it really easy. He also took some amazing photos throughout the trip, which was a great bonus and gave us some brilliant memories to take home. Overall, a really enjoyable trip with a great mix of adventure, sightseeing and downtime. Madeira is an incredible destination, and WeRoad was a great way to experience it with a fun group of people. I’d definitely recommend it.Maz11/08/2026
What a trip!! This is the perfect trip for those who love adventures by both land and sea. Madeira is truly a place full of magic and this trip allows you to explore the wonder of one of the worlds most beautiful islands.May Rose B.05/07/2026
At 48 years old, I was probably the "dean" of the group – and I'm actually a little proud that I kept up with the pace so well. 😊 But you shouldn't underestimate that a certain basic fitness is necessary for it. The group was simply great. It was incredibly fun to be on the go together, and the great atmosphere made the entire time even more beautiful. Special praise goes to the coordinator. She did a really excellent job. The organization was top-notch, everything ran smoothly, and you could tell how much commitment and passion she had for it. I am completely satisfied and can hardly put into words how much I have experienced in such a short time. Never before have I gathered so many beautiful impressions and seen so much in just a few days. Every day was full of special moments. In the end, I was quite exhausted, but at the same time overjoyed about everything I was allowed to experience. I'm taking countless beautiful memories home with me and am grateful that I was able to be a part of it. An experience I will not forget. ❤️Zojneta K.13/06/2026
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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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About this trip

About WeRoad

About Madeira

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