Hiker with backpack overlooking steep cliffs and turquoise sea at Ponta de São Lourenço
Hiking along the Levada do Caldeirão path next to a dark blue rock face overlooking a lush green valley.
Coastal view of Cabo Girao with steep cliffs, pebble beach, blue ocean, and town on hillside.
Hikers on viewing platform above clouds on rugged peaks from Pico do Arieiro to Pico Ruivo.
Coastal town with white buildings and terraced green hillsides meeting deep blue water with boats, Funchal.
Levada do Norte hiking path alongside a water channel with lush greenery and mountains.
Hiking trail above clouds at sunrise over rugged mountains in Madeira.
Natural seawater swimming pools by the ocean with a village on a steep hillside in Porto da Cruz.
Traditional thatched-roof houses along a cobblestone path in Queimadas Forest Park.
Tunnel on Levada do Norte with illuminated stone walkway curving through dark rock.
Waterfall in Levada do Caldeirão Verde surrounded by lush green ferns and dense forest foliage.
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Eastern Madeira Walking Holidays

8 days / 7 nights

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Discover the enchanting allure of Madeira, from rugged cliffs and serene Levadas to verdant forests and hidden waterfalls on these captivating walking holidays.

Starting point

Funchal

Finish point

Funchal

Season

From April to October

Technical level

3/5

Fitness level

3/5

Tour type

Travel & Hike

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Highlights

  • Experience the mesmerizing views from Pico Ruivo, Madeira’s highest peak
  • Immerse yourself in the vibrant culture of Funchal and its lively Mercado dos Lavradores
  • Witness the dramatic rock faces of Cabo Girão rising from the ocean
  • Explore the secluded corners of the island, like Faja Escura
  • Savor the diverse flora and fauna of Madeira as you traverse its picturesque trails
  • Enjoy the convenience of organized transfers to the starting points of your hikes

What’s included in the price?

Self-guided

7 nights in 3-star hotels with breakfast
Digital guidebook with itinerary, route instructions, and practical information
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your hike

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Luggage transfer
Single supplement
Transfers to/from start/finish points

What to bring to the tour

  • Hiking shoes/boots
  • 25 to 35-liter backpack
  • Base layer
  • Sports T-shirts
  • Hiking shorts
  • Hiking water-repellent pants
  • Waterproof jacket
  • Midlayer
  • Sports socks and underwear
  • Leisurewear for evenings
  • Shade hat/cap
  • Sunscreen
  • Sunglasses
  • Hiking poles
  • ID card or passport
  • Snacks
  • Cash
  • Water bottles or hydration pack
  • Toiletries

Head on an unforgettable journey across Madeira's diverse landscapes, where sun-kissed beauty meets lush forest enchantment. Your adventure unfolds from the vibrant atmosphere of Funchal, weaving through the island's contrasting terrains and unique features, culminating at the awe-inspiring cliffs of Ponta de São Lourenço.

As you venture deeper into Madeira, you'll explore the coastal charm of fishing villages along the northeastern coast, feel the adrenaline of reaching the summit of Pico Ruivo, and immerse yourself in the enchanting Laurisilva forest.

Nature lovers will rejoice as they encounter numerous waterfalls and tunnels along the Levada do Caldeirão Verde, while the breathtaking Cabo Girão viewpoint provides a stunning finale to your Madeira adventure.

Throughout your trip, we'll be on top of all the details, from handouts with day-by-day itineraries to GPS navigation, insider tips, and round-the-clock support. We'll also arrange accommodation bookings and organized transfers, ensuring a stress-free experience.

While we believe the self-guided nature of this tour provides the ultimate freedom and flexibility to appreciate Madeira, rest assured that should you desire a local guide to enhance your experience, we're more than happy to accommodate your wishes.

Lace up your walking shoes and join us on this Madeira adventure that will leave you with memories as rich and diverse as the island itself. After all, life's too short for ordinary vacations!

Frequently Asked Questions

Our walking holidays try to accommodate a wide range of hikers while preserving the overall quality. We try to keep the stages as undemanding as possible, but you have to understand that, on Madeira, some of the highlights are slightly secluded, and they require a certain amount of effort to reach. You should be used to walking for up to 6 hours on certain days while overcoming nearly 800 meters of elevation.


Nevertheless, most of the hikes return the same way, so you can always turn around sooner than planned if you feel you will not make it back comfortably. And the trails themselves are not technically demanding as you are walking upon well-beaten tracks along Levadas and Veredas. You must have a head for heights for some of these hikes, as some sections can be exposed. They are well-secured, but you should not underestimate them if you are at risk of vertigo.

Most of these hikes can be done with children if they are used to walking and heights. We wouldn’t advise them to be younger than ten years, but you should judge whether they are capable of hiking for multiple hours.

Proper footwear is crucial for our walking tours. We recommend wearing sturdy hiking shoes with ankle support for all our hikes. Even though the paths are mostly beaten or even paved, such shoes come in handy when you are tired or it gets wet. Wearing sneakers can be dangerous, especially if you are not accustomed to hiking on such surfaces, as they do not offer enough protection and support. Robust shoes also provide the necessary support when your legs get tired during long hikes.

We strongly recommend booking in advance to secure your spot, as this will increase your chances of getting your preferred options. If you wait until the start or during the season, we may not be able to guarantee availability in the hotels and apartments. Therefore, it’s best to make your reservations as soon as possible to avoid any inconvenience. Madeira is a popular tourist spot, after all, and the accommodations get booked fast.

Please note that during the hiking season, accommodations in the destinations of our walking tours are in high demand. Thus, it is essential to book early to secure your preferred type of housing. However, we want to assure you that we will always strive to provide you with the most suitable lodging based on your preferences. You can rest assured that we will do everything in our power to ensure your stay is comfortable and enjoyable.

Our tours are well-planned, and all the destinations are easily reachable and straightforward to navigate. Therefore, it’s unlikely that you’ll need a guide. Our detailed handout will provide all the necessary information while allowing you the flexibility of a self-guided vacation.


However, if you would like to have a guide, please inform us, and we will make the appropriate arrangements for you.

Most of the accommodations offer vegan and vegetarian meal options, and we can arrange either for you after you let us know through our inquiry form. Similarly, you won’t face many issues finding restaurants with such options as Madeira offers a variety of different dining places.

While people tend to visit Madeira during summer, such a time is not the optimal choice for hiking and walking. The temperatures are high, and the sun is beating down on you tirelessly. If you are visiting in summer, you can rather visit the island’s magical beaches and soak in the refreshing Atlantic Ocean.


The best time for a walking holiday in Madeira is generally between April and May and between September and October, as the weather is mild and pleasant during these months. Spring (April-May) offers beautiful blooming flowers, while autumn (September-October) presents a vibrant display of foliage. However, Madeira boasts a mild subtropical climate year-round, making it a suitable destination for walking holidays even during winter, although you may encounter more rainfall and cooler temperatures. Ultimately, the choice depends on your personal preferences and desired walking conditions.

Ratings & Reviews

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Nuša Bobik

Verified customer · 8 months ago

Exploring Madeira on foot was an incredible adventure. The trails offered a variety of experiences, from dramatic cliffside paths to lush levadas (irrigation channels) winding through the forests. The island’s unique landscapes were unlike anything I’ve seen before. Samo was fantastic, providing clear guidance and tips on which trails to prioritize based on my interests. The accommodations were excellent, and the local cuisine was a delightful bonus. This walking holiday introduced me to the wonders of Madeira, and I’ll definitely be back!

Radhika Arun

Verified customer · 4 months ago

Did the Eastern Madeira walking holiday. The hikes were lovely though some were crowded. But they were crowded cause the view was great. So can't skip loved the ocean side cliffs for a couple days and then the forests along levadas. We had a misunderstanding with the driver as he thought we should have finished sooner. So give them a reasonable estimate. He never asked and his estimate caused all the issues. But we whatsapped the company and they set it straight. Food is good in the towns. We packed lunch everyday as some of those places along the way had long lines. We went a day early and did a sightseeing day with their driver and it also helped with jet lag. Hikes are pretty moderate, so you have energy to enjoy the town in the evenings. The Island is beautiful ❤️

Aurore Kurc

Verified customer · 9 months ago

I did the Fisherman Trail in Portugal mid April and I had a fantastic time. The trip was well organized and the luggage transfer seamless. The maps were clear and easy to navigate, and always got me to my destination safe and sound. And the accommodations felt like a complete splurge, especially the B&B. And of course the views along the trail were amazing. Definitely would recommend booking with them!

Lynne Davidson

Verified customer · 4 months ago

I had a wonderful 9-day experience of walking & cycling through Slovenia. I really appreciate how this company provided excellent support and assistance as needed each day.

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Jim Carey

Verified customer · 6 months ago

Our holiday was fantastic, really well planned with excellent communication and the app worked a treat for our day to day activities. If you're thinking of a walking / hiking holiday and are unsure of where to go or how to plan it, this is the job for you

Hiking trail on grassy slope overlooking green valley and steep mountains under cloudy sky

Kris Hoban

Verified customer · 6 months ago

Walking Holidays Slovenia is great! They provided all of the information and made the arrangements for our self guided walk in Triglav National Park. We hiked to Vodnikov Dom the first day, then to the Seven Lakes Basin the second day, then back to Ribcev Laz the third day. The trails were well marked, and the GPS app recommended by Walking Holidays Slovenia was very helpful for keeping us on track. The trails were very rocky in places, which was a bit of a challenge for us, but it was so beautiful! Very much recommend this company!

Hikers resting on wooden deck of mountain hut overlooking rocky peaks and forested valley
Wooden mountain hut with solar panels in a meadow below rocky peaks and pine trees.

All available guidance options

Join a Group

Don’t want to hit the trails by yourself? No problem! We’ll find you a group of like-minded hikers and handle all the logistics. Guided by our experienced leader, you'll enjoy a stress-free journey focused on what truly matters – soaking in the trails, meeting new people and making unforgettable memories.

Private Guided Group

Get together a group of your buddies and leave the rest to us! All you have to do is sit back, relax and enjoy a tour built around your group’s preferences. With an experienced guide accompanying you every step of the way, you’ll get the most out of your hike without having to stress about the details.

Self-guided

Are you looking for a good adventure and limitless flexibility? Then you should try out a self-guided tour, perfect for independent explorers who want to set their own pace. Without the need to stick to a group schedule, you’re free to linger at scenic viewpoints while the logistics are taken care of in advance.

Hassle-Free

We handle route planning, accommodations, transfers, and anything else you prefer not to deal with, so you can enjoy a carefree hike.

Tried & Tested Adventures

Only the best hiking adventures in Portugal, cherry-picked by our local team with an in-depth knowledge of the region.

Book With Confidence

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Unbeatable Support

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

from 1.350 € /person
We help you discover every magical corner of the most breathtaking island in the Atlantic on our guided or self-guided walking holidays in Madeira.

Have questions? Talk to us.

Anja Hajnšek
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