Madeira 360°: Hiking & Canyoning on Europe's Wildest Atlantic Island




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.


Welcome to Madeira: Funchal Check-in
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.
First dinner together: our first taste of Madeira is more likely fresh fish straight out of the Atlantic than fennel, eaten slowly while the group gets to know each other.

Canyoning and the Streets of Machico
Ready for canyoning?
Adrenalin first thing! A river gorge before any town. With its water-carved gorges, waterfalls and lush vegetation, Madeira is considered the best in the world for this.
Down the river: canyoning means descending a river by climbing, swimming, sliding and jumping.
Machico and a sunset miradouro
After lunch and a chance to recover, we take the cars to Machico, Madeira's second largest city.
Through the old centre: we walk the narrow streets of the town centre down to the seafront promenade, full of cafes.
Bolo do caco and sunset: bolo do caco with a sea view, then sunset from the Francisco Alvares Nobrega Miradouro over Ponta de São Lourenço.

Trekking Pico do Areeiro to Pico Ruivo
The eternal spring
A dawn start, because the island where it is always spring keeps its very best scenery high above the coast.
From Areeiro to Ruivo: 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.
The final push: one last climb to the summit. The overhangs are daunting, but the path is safe and handrailed.
Lunch and back: a packed lunch, then the same trail back to the cars.

Achadas da Cruz, Fanal and Porto Moniz Pools
The EU's steepest cable car
Another early start, for the north-western tip of the island.
Cable car down the cliff: 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.
Farmland by the sea: below it, a different microclimate, with unspoilt farmland, small houses and traditional wine presses, plus a seaside promenade rated among the island's finest photo spots.
A drink with the locals? Locals sometimes serve drinks at home for a donation.
Porto Moniz, Fanal and Seixal
Via Porto Moniz and its natural lava pools, we continue along the north-west coast.
Time for the Fanal? If time allows, we detour to the Parque Florestal do Fanal, an ancient laurel forest cloaked in thick mist.
A swim at Seixal: then the black-sand beach of Seixal and a plunge into the Atlantic Ocean at a pleasant 20 degrees.
Last miradouro: the Véu da Noiva waterfall stays in the distance, with a miradouro stop before Funchal.

Ponta de São Lourenço and Sunset Boat Trip
Trekking with a view
Hiking in the morning, sailing in the afternoon. Coast or inland?
Out to the eastern tip? 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.
Or into the green? 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.
Snorkelling at anchor: we stop for snorkelling, with equipment on board and a drink for anyone staying dry.

Cabo Girão and Ponta do Pargo
The island from above
South coast day, mostly from viewpoints. Got a head for heights?
Starting from Câmara de Lobos: the town hosted Winston Churchill in 1950; from here we climb a little towards the vertigo test.
On the glass at Cabo Girão: 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.
Sunset at Ponta do Pargo: 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.

Nossa Senhora do Monte and Mercado dos Lavradores
Sledding in Madeira?
One last day on Madeira, with a cable car up and something considerably stranger on the way down.
Cable car to Monte: 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.
Down by toboggan: 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.
A stroll through the market? The Mercado dos Lavradores in central Funchal has the freshest fruit, flowers, intricate crafts and souvenirs.

Check-out and Goodbye in Funchal
See you soon, Madeira
Eight days gone, and this is check-out morning in Funchal. Time flies when you are having fun!
Check-out: we check out, sort the bags 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
7 nights accommodation in a shared room for the duration of the trip
All breakfasts
Sunset boat trip with drinks
An adrenaline-pumping canyoning experience
Car rental from Day 1 to Day 8
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
What's not included
- 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
- 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
Reviews
based on 538 verified reviews
Rating breakdown
- 5 stars80%
- 4 stars17%
- 3 stars3%
- 2 stars0%
- 1 star0%
Irina-Alexandra2 WeRoad trips done
5September 2026
Absolutely amazing Madeira trip with WeRoad! 🌿🌊⛰️ This was my first WeRoad trip, and I honestly couldn’t have asked for a better experience. Madeira itself is absolutely stunning, but what made the trip so special was the combination of adventure, incredible places, and an amazing group of people. The itinerary was packed with highlights: hiking through some of Madeira’s most spectacular landscapes, canyoning, exploring Funchal, swimming and enjoying the coast, visiting Porto Moniz and Fanal, and so many beautiful viewpoints along the way. There was always something happening, but it never felt like we were just ticking places off a list. A huge part of the experience was our group and our captain, Elle. Everything felt easy, spontaneous and fun, and there were plenty of moments that I know I’ll remember for a long time. From hiking together to dinners, drinks and all the random little moments in between, it felt much more like travelling with friends than joining an organised trip. Madeira was already high on my travel list, but this trip completely exceeded my expectations. If you love adventure, nature, good food, beautiful views and meeting new people, I’d absolutely recommend doing Madeira with WeRoad. ❤️ Already looking forward to the next adventure! ✈️
Anca Elena First WeRoad
5June 2026
I recently joined my 1st WeRoad trip to Madeira and overall it was a very well-organized and memorable experience. The itinerary was thoughtfully planned and delivered on what was advertised, covering a wide range of highlights across the island. There was also good flexibility to adjust plans when needed, and the balance between structured activities and free time worked well, allowing space to both explore and rest. The group dynamic was excellent, and the coordinator did a great job keeping everything running smoothly. We managed to experience a mix of hiking, scenic walks, sailing, and key spots across Madeira—far more than I expected in one week. The trip felt full, active, and visually stunning throughout. That said, a few things could be communicated more clearly in advance. Some additional costs were not fully transparent beforehand—such as certain hikes and transportation between activities—which came as a surprise despite the initial expectations from the website. Food arrangements were also quite structured, with several pre-booked restaurants, which may feel limiting for those who prefer more flexibility or earlier dinners. Overall, there was still enough downtime, but clearer upfront communication around extra costs and scheduling would improve the experience. In summary, it was an incredible, well-run trip with great people and a strong itinerary, just with a few important details that future travelers should budget and prepare for. I would definitely join future trips 😊
RalucaFirst WeRoad
5June 2026
I went into this trip slightly anxious, wondering if I will get along with the people who joined and if it will be trully as good as advertised (which I discovered is a very common question among 1st time weroaders like myself). Happy to say that these doubts got dispelled on the first day when I met my fellow travellers and started experiencing the island together. The Madeira 360 trip was amazing not only because of the great places we visited, but also because of the great group of people that embarked on this journey. Jason, who was our group leader, played a pivotal role in organising all the activities smoothly and keeping our minds fully focused on enjoying them and connecting with each other. At the same time, he integrated in the group really well as a fellow traveller & friend, rather than giving tour guide vibes. I also thoroughly enjoyed the diversity of things we got to do and places we got to see: from adventures that push our limits (e.g. canyoning, surfing) and hikes with breathtaking views to relaxed time on the beach and wine tasting. There was definitely something for everyone on this trip. But what I loved most was that there was room for spontaneity inbetween all the itinerary objectives and for everyone to be themselves, which is what created the most wonderful memories of the trip. The words in this review don't do justice to how much fun I had on this trip, the life-long memories I take with me and the friendships I've built. Madeira will always have a special place in my heart because of WeRoad and I can't recommend it enough!
DanielFirst WeRoad
5October 2026
This was a great experience, so many great places to see and activities to do
May Rose2 WeRoad trips done
5June 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.
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
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