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Portugal – Deluxe Madeira Island Hiking Tour

(3 Reviews)

Madeira Portugal Self-Guided Hiking Tour: Discover Madeira’s breathtaking landscapes on this self-guided hiking tour, where you’ll explore towering mountains, dramatic cliffs, and historic levadas, the island’s unique irrigation channels turned scenic hiking paths. Marvel at rock formations and deep gorges shaped by erosion, and wander through the Laurissilva Forest, the world’s largest laurel forest and a UNESCO Natural World Heritage Site. The island’s diverse terrain offers both serene coastal walks and exhilarating high-altitude trails, ensuring a rewarding adventure for hikers of all levels. With stunning views and rich natural beauty, this journey promises an unforgettable experience in “The Pearl of the Atlantic.”

Get your adventure:   
1. Call or email with Questions:  +1-970-230-5896 or email us. 
2. Book the trip, pay a deposit, get excited for your adventure!
Book This Tour

Arrival & Departure Locations

Fly in and out of Funchal Airport, via Lisbon or other. Tour starts in Santa Cruz and finishes in Funchal. All airport transfers are included.

Price Includes

  • Flexible private departure on your own travel dates!
  • 7 nights in deluxe accommodations – Relax in comfort after each day’s adventure
  • Daily breakfast included – Enjoy a fresh start every morning
  • Private welcome orientation in English – Personalized tour details and daily recommendations
  • Private airport transfers – Seamless arrival and departure from Funchal Airport (FNC)
  • All private transfers during the tour – Convenient transport to and from hiking locations
  • Comprehensive Digital Hiking Information Guide – Everything you need for a seamless experience
  • GPS tracks with a navigation app – Stay on course with easy-to-use digital mapping
  • Liability and personal accident insurance – Travel with peace of mind
  • Pre-travel documentation and trip preparation details – Get ready with all necessary info

Not Included:

  • Additional meals/activities outside of the itinerary
  • Starting in 2025, some hiking trails may require a small trail fee, payable on-site

Lodging

Included Deluxe Hotels:
  • Santa Cruz: Vila Gale Santa Cruz **** (2 nights)
  • Santana: Hotel Quinta do Furão **** (1 night)
  • Encumeada/Arco de São Jorge: Pestana Quinta Do Arco **** (1 night)
  • Porto Moniz: Aqua Natura Bay **** (1 night)
  • Ponta do Sol: Ponta do Sol Inn **** (1 night)
  • Funchal: Castanheiro Boutique Hotel **** (1 night)
About: Our standard tour offer includes hand-picked 4 and 5-star hotels in convenient locations in each town along the tour’s route. All lodging includes a private bathroom and a variety of other amenities. All lodging is subject to availability at the time of receiving your booking request and deposit.

Optional Add-Ons

Guides & Local Support


Local Expert:
Antonio is our on-site expert. He lives in Lisbon and has been all over the country! Antonio will meet you for orientation on arrival day as well as provide emergency support throughout your trip. Our local guides and experts are available by phone to assist during your trip with any kind of emergency and if due to weather or other reason you need to arrange a transfer. 

Tour Highlights - Madeira Self-Guided Hiking Tour

  • Flexible private departure – Travel when you want to!
  • Spectacular mountain scenery – Towering peaks in the heart of the Atlantic Ocean
  • Protected wildlife areas – Part of the renowned “Natura 2000” network
  • Madeira’s highest summits – Breathtaking views from the island’s highest peaks
  • Iconic levadas – Scenic trails through volcanic landscapes and lush forests
  • Laurissilva Forest – A UNESCO Natural World Heritage Site, home to ancient laurel trees
  • Quaint fishing villages – Experience the charm and authenticity of Madeira’s coastal communities
  • Historic Funchal – Explore the vibrant Old Town with its rich culture and heritage
  • Delicious local cuisine – Fresh seafood, regional specialties, and exquisite Madeira wine

Need to Know:

  • The region enjoys mild temperatures year-round, but rain can occur at any time. Guests should bring rain gear and a headlamp and be prepared to hike in all weather conditions.
  • Despite the remote Atlantic setting, you’ll be surrounded by lush green fields, breathtaking coastal views, rainbows, and warm, welcoming inns—making it easy to forget how far from the mainland you are!
  • Each hiking day includes a transfer to the trailhead and a transfer back to the hotel at the end of the hike.
  • Starting in 2025, some trails may require a small user fee, payable onsite only.
  • Trail routes are subject to change due to weather conditions or natural events.
  • Portugal Travel Resources
  • Travel Insurance is required on all Pure Adventures tours.

Photos
Itinerary

Day 1Arrival Day

Upon arrival for your Madeira self-guided hiking tour, our friendly guide will warmly welcome you at the airport and accompany you to Santa Cruz, a charming coastal town just a 10-minute drive away. Once there, you’ll check in to your accommodation and have the rest of the day to unwind.

Relax by the inviting swimming pool, soak up the sun with breathtaking mountain views, or simply enjoy the peaceful surroundings. Whether you opt for a leisurely swim, a refreshing drink by the pool, or some quiet time with a good book, Santa Cruz provides the perfect setting to ease into your adventure. This tranquil escape is the ideal way to begin your unforgettable Madeira hiking experience.

Overnight: Santa Cruz

Day 2Hike from Ponta S. Lourenco: 8 km / 5 mi

Start your day with a short 20-minute transfer to Ponta de São Lourenço, where the trail winds around the volcanic peninsula to Madeira Island’s easternmost point. From here, take in stunning views of the Atlantic Ocean and nearby islets. The Desembarcadouro Islet and peninsula are designated as a natural reserve, while the land and sea along the northern coast—up to 50 meters deep—are part of the European Natura 2000 network. It’s a day of truly spectacular scenery, so embrace every breathtaking view and the island’s incredible natural beauty!

Meals: breakfast
Distance: 8 km / 5 mi, +300 m
Highlights: Desembarcadouro Islet & magnificent views
Overnight: Santa Cruz

Day 3Hike from Machico to Porto da Cruz: 17 km / 11 mi

Today, let’s head to Facho Pic (322 meters) and take in the stunning northern coastal views. Immerse yourself in a lush landscape where cascading water creates a soothing natural symphony. Marvel at the breathtaking scenery of maritime pines, eucalyptus, and the dense vegetation of the native Laurissilva forest.

Following the Levada, you’ll encounter Canary Willows, towering Madeira Laurels, Madeira Mahogany, and Lily-of-the-valley trees. The hike unfolds like a series of scenic windows, opening up to small rivers, tranquil lakes, and cascading waterfalls.
After your adventure, your hotel awaits, offering a chance to relax. But if you still have energy, don’t miss the chance to visit the inviting natural pools in town!

Meals: breakfast
Distance: 17 km / 11 mi, +400 m
Highlights: lush vegetation, scenic levada walk, natural pools
Overnight: Santana

Day 4Hike from Pico Ruivo to Encumeada: 14 km / 9 mi

Today’s hike features steep climbs and descents through one of Madeira Island’s most picturesque regions. Though challenging, the trail rewards you with breathtaking scenery, particularly near Pico Ruivo. Begin with a transfer to Achada da Teixeira, just below Pico Ruivo, and follow the central mountain range westward toward Encumeada, crossing two distinct Natura 2000 ecosystems. Walk through the ancient Laurissilva forest and take in the dramatic volcanic escarpments of the Central Mountain Massif.

As you near your accommodation in the Encumeada Valley, soak in panoramic views—perfect for capturing unforgettable photos and quiet moments of reflection. This journey offers an unparalleled opportunity to connect with Madeira’s extraordinary natural beauty.

Meals: breakfast
Distance: 14 km / 9 mi, +600 m
Highlights: Pico Ruivo – the highest peak on Madeira, Encumeada, beautiful landscapes
Overnight: Encumeada Valley (Arco de São Jorge)

Day 5Hike from Paul da Serra to Fanal: 11 km / 7 mi

After a morning transfer, begin your exploration of the Paúl da Serra plateau, a breathtaking highland offering panoramic views. Follow the trail to several scenic viewpoints, where sweeping landscapes reveal the valleys of Ribeira da Janela and Chão da Ribeira. The path winds through the ancient Laurissilva forest, a UNESCO World Natural Heritage site and a protected part of the Natura 2000 network.

At the end of your hike, arrive at the magnificent Fanal, a serene volcanic crater designated as a resting reserve within the Parque Natural of Madeira. This enchanting area is defined by its mist-covered Til trees and awe-inspiring vistas, making it a truly memorable stop along your journey.

Meals: breakfast
Distance: 11 km / 7 mi, +200 / -500 m
Highlights: Paúl da Serra plateau, protected valleys & forest, Fanal crater
Overnight: Porto Moniz

Day 6Hike from Jardim do Mar to Paul do Mar: 6 km / 4 mi

Today, embark on a heritage-rich journey through western Madeira, following an ancient trail that links Prazeres to the picturesque coastal village of Jardim do Mar. Once one of the few routes connecting the inland communities to the sea, this historic path descends nearly 500 meters, offering a perfect opportunity to soak in breathtaking coastal landscapes, terraced farm plots, and centuries-old stone walls.

Designated as a municipal path, this trail stands as a testament to the resilience and ingenuity of past generations, who carved out challenging routes to bridge their isolated mountain villages with the coastline. Before returning to your hotel, take time to explore Paúl do Mar, a charming fishing village with a rich maritime history and a quaint seaside church that adds to its timeless appeal.

Meals: breakfast
Distance: 6 km / 4 mi, +600 / -550 m
Highlights: heritage/municipal walking path, fishing village
Overnight: Arco da Calheta

Day 7Fun Free Day in Funchal

After a scenic 60-minute transfer to Funchal, you’ll have the day to explore Madeira’s vibrant capital at your own pace. Stroll through its cosmopolitan city center, uncover rich history at landmarks like the Cathedral, and take in stunning ocean views from the best lookout spots. Be sure to visit the bustling market, where you can savor the island’s finest gastronomy—from sizzling meat skewers to sweet banana cake and the beloved traditional poncha. A day in Funchal is a feast for the senses, offering the perfect blend of culture, history, and flavors

Meals: breakfast
Highlights: Funchal exploration
Overnight: Funchal

Day 8Departure

Today it is your last day and it is time to pack up the good memories and say goodbye! Our guide will transfer you to the airport at 10:00 AM or according to your time schedule. We hope you enjoyed your self-guided Madeira hiking tour!

Meals: breakfast

Map
Dates & Rates

Dates: Plan your trip at a time that best fits your schedule! Pure Adventures tours have flexible start dates.

2025 Tour Rates by Season: (based on double occupancy)

Superior Three & Four Star Hotels:

  • January – February:  2007 euros/person
  • March: 2054 euros/person
  • April (excluding holidays): 2133 euros/person
  • April Holidays (Easter & Flower Fest):  2481 euros/person
  • May – October:  3270 uros/person
  • November – December: 2007 euros/person
  • Single Supplement: ranges from 522 to 720 euros; please ask us for rates

Ways to Save! Groups of 6 adults or more: 10% discount. Children under 15 recieve 30% discount.

New! Travel Insurance is now required to participate in this tour. You can book through our preferred vendors or your own. Proof of coverage will be required.

Make it Custom: Do you like this tour but want to make it different? Tell us your wishes & we will quote them!

How do our tours compare to similar trips? You Get More
If you compare prices, we are much less than guided trips with similar experiences. In our private, independent format, you get much more than what most traditional self-guided tours offer, plus it’s a better experience! Our team has gone to great lengths to build and create exceptional tours all over the world, vacations that will give you lifelong memories. We hold each component of our tours to a very high standard, and we are dedicated to empowering people through travel!
 
What Next:   
1. Call or email with Questions:  Our well-traveled, knowledgeable, and dedicated team is standing by and eager to make your travel dreams come true. Call now at 800-960-2221 (USA/Canada 8 am-5 pm MST) +1-970-230-5896 or email us. 
2. Book the trip, pay a deposit, and get excited about your adventure!
Book This Tour
3 Reviews
Sort By:RatingDate

Bryan & Stacey

Couple Traveller

Madeira is stunning! Bryan and I couldn’t decide what we liked more, the beautiful landscapes or the hotels!

Everything went smooth for our tour with pick ups and GPS tracks we had the perfect amount of support without the hassle of being on a group tour with a guide. We want to come back and do this trip again when our kids are a little older!!!

September 2, 2022

Ashleigh Beck

Family Traveller

Our time in Madeira far exceeded our expectations, as did the resources provided to us by Pure Adventures for our big hiking adventure. We enjoyed the hotels and local recommendations included in our digital tour booklet. This was a useful tool, as was our GPS routing. The hikes are challenging but rewarding! Only downfall was a day of rain, but that is part of travel!

April 6, 2021

Steven Sorenson

Couple Traveller

Excellent hiking tour. No issues to note, loved Maderia – food, people, scenery. Third tour with Pure Adventures!

June 6, 2019