Hiker on PR1 Pico do Arieiro - Pico Ruivo trail Stairway to Heaven Madeira PortugalPonta de Sao Lourenco peninsula with beautiful flowers in the foreground in the Madeira Islands, Portugal.Jungle in Madeira island - Views from the trekking trail on the cliffs at Levada do Caldeirao Verde, Queimadas, PortugalWoman hiking on Madeira Island in Portugal"Stairs to heaven" - Breathtaking view at famous mountain footpath from Pico do Arieiro to Pico Ruivo on the Portuguese Madeira island. Trekking Around the world traveling with kids concept image.

Madeira Island Hiking Adventure

Funchal, Madeira
5.0 (2 reviews)

Trip Highlights

  • Island Hiking on Madeira
  • Floating Garden on the Atlantic: rich flora and fauna
  • Wild Coastlines, Mountains, Waterfalls, Quaint Villages
  • UNESCO Designated Primary Laurel Forest
  • Portugal Vacation Package to the "Island of Eternal Sun"
  • Elegant European Accommodations & World Class Cuisine


Join us on this Portugal trekking tour to the island of Madeira! Madeira is an incredible hiking destination with stunning North Atlantic seascapes, volcanic landscapes, massive waterfalls, and truly world class trails.

Together, we’ll experience jaw-dropping views as we trek around this island with dramatic cliffsides, immense waterfalls (one over 300 ft tall!), UNESCO designated primary Laurel forests, and 16th century irrigation aqueducts (levadas).

Each night we’ll stay in quaint European towns and boutique accommodations sampling the delicious cuisine of the region. If you enjoy wine, our dinners will include samplings of some that Madeira is known for. With a knowledgeable local guide, you’ll have an insider’s experience of the island of Madeira. Don’t miss this amazing opportunity to experience the best of Madeira!

Looking to explore even more of Madeira? We have you covered with a 1 night/2 day, 4-star lodging package that includes admission to the world-renowned Porto Moniz lava pools. With private transfer to/from Funchal and Porto Moniz and your hand-selected accommodations booked for you, you’ll have time to relax and enjoy an exquisite piece of the North island. Click here to read more about our Porto Moniz Add-On Package!

Read more …
From USD
$3750 Per Person


Trip Type: Inn-Based Hiking Tour
Difficulty Level:
Solitude Level:
Group Size: 2-12 Guests
Trip Length: 8 Days
Distance: 40 MI / 63 KM


Scale of 1-5. 1 is least difficult; 5 is most difficult

This trip involves hiking with a light day pack (8-12 lbs) from 3-5 hours a day with elevation gain and loss averaging around 1200 ft. This trek features sustained significant to extreme exposure to heights with roped barriers on exposed sections.

Hiking Distances:

Up to 7 miles

Backpack Weight:

Up to 12 lbs


Moderately Rugged

Max Daily Elev. ↑↓:

Up to 2,700 feet

Heights Exposure:

Extreme Exposure

This trip involves hiking with a light day pack (8-12 lbs.) from 3-5 hours a day with elevation gain and loss averaging around 1200 ft. This trek features sustained significant to extreme exposure to heights with roped barriers on all exposed sections.


  • Hiking uphill or downhill with an 8-12 lb backpack for 3-5 hours a day
  • Maintaining balance and footing on steep, variable and uneven terrain
* For an official and complete list of physical requirements, please see our Essential Eligibility Criteria.


1 least solitude, 5 most solitude

We rate this Madeira Island Trek a solitude 2. You can expect several hours of solitude at a time.

Minimum of 3 Guests

We require a minimum of 3 guests to confirm this trip. If a trip date is not confirmed yet, you can register and will be notified when the trip is officially confirmed. We recommend not making final travel arrangements until your trip meets the minimum number of guests and is confirmed.

In most cases, if a trip does not reach the minimum number of guests, you may choose to transfer to another trip date or another trip, be refunded your payments in full, or you may have the choice to pay a supplemental fee to run the trip with fewer guests. We make the final determination for these trips 65-60 days before the departure date.

Private Trips

Travel in perfect company by booking a private trip exclusively for your group!

Our sliding scale for private trips is based on the final number of guests in your group. Rates are per person and do not include sales tax, national park fees or guide gratuity. The final rate is based on the actual number of guests on the trip and may adjust based on cancellations or additions.

Please Note: you can also enjoy a private trip at our normal scheduled rates by filling any empty tour to capacity. However, if group members drop from the tour those spots will automatically become available on our website for instant booking. By purchasing a private trip at the rates listed below, your trip will remain exclusive to your group regardless of cancellations. 

Private Rates FOr This Trip

  • 2 people: rate x 2.5 (min 4 on some trips)
  • 3 people: rate x 2
  • 4-5 people: rate x 1.5
  • 6-10 people: rate x 1.15
  • 11-12 people: standard rate
  • 13+ people: contact us for availability and pricing

*all rates are per person and single supplements apply

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Day 1

Welcome to the wonderful and mesmerizing island of Madeira with its high cliffs, pebbly beaches, deltas, and beautiful greenery. We will meet you in the afternoon at Madeira Airport International Cristiano Ronaldo in Funchal, where we’ll transfer to our 4-star accommodation overlooking the Bay of Funchal. You will have some time to rest after your travels, enjoy the panoramic view of the Bay from the pool, or walk around the shops and museums that are nearby.

We will meet as a group for orientation before enjoying our first Madeiran dinner.

Day 2

  • Hiking Mileage: 4 mi (7 km)
  • Elevation Gain: 1378 ft (420 m)
  • Elevation Loss: 1378 ft (420 m)
  • Drive Time: 40 min.

It’s an exciting day as we take off to Ponta de Sao Lourenço! After a 40-minute private transfer, our coastal hike takes us to the easternmost point of the island. This point combines the fury of the Atlantic with basalt formations, the largest Caspian gull colony in Madeira, as well as endemic plant species. From this point you’ll be able to see the north and south sides of the island. This trail is often dubbed “The Dragons Tail” and once you set eyes on this incredible landscape jutting into the sea, you’ll know why. As we wind our way towards the tip of the island, we’ll have views of many small islets, and we’ll even see agave plants with stems reaching 16 feet tall!

Day 3

  • Hiking Mileage: 7.5 miles (12 km)
  • Elevation Gain: 820 ft (250 m)
  • Elevation Loss: 1475 ft (450 m)

This morning starts with a vehicle transfer to one of the island’s most treasured hikes: the Boca do Risco Pass. This trail was originally used to connect the city of Machico to Caniçal and Porto da Cruz, allowing local merchants to transport and trade goods. Today you’re more likely to encounter trail runners and continental hikers on this historic trail. We’ll climb up over Machico to the Ribeira Seca levada, then towards the pass while looking out over the sea. This hike hugs the cliff with the trail being cut right into its side! From this path we’ll be able to glimpse the tip of São Lourenço and the distant isle of Porto Santo. Another short transfer takes us to the hotel in Santo da Serra.

Day 4

  • Hiking Mileage: 7 miles (11 km)
  • Elevation Gain: 1312 ft (400 m)
  • Elevation Loss: 656 ft (200 m)
  • Drive Time: 35-40 minutes

Today’s hike along the Levada do Furado takes us on one of the most beautiful walks in the East of Madeira. This particular Levada is one of the most frequented and oldest public lands in the area. On this hike you’ll witness various endemic tree species, other varied flora, and uniquely designed farmlands of Faial and São Roque do Faial. A wide path become gradually narrower as we eye towering peaks and peek down into undulating ravines. We’ll walk along extraordinary balconies in Ribeiro Frio before a short transfer to our hotel.

Day 5

  • Hiking Mileage: 6 miles (9 km)
  • Elevation Gain: 1805 ft (550 m)
  • Elevation Loss: 2297 ft (700 m)
  • Drive Time: 1 hour

We’ll start the day with a 30 minute transfer to Pico do Ariero: our starting point for the day and another of Madeira’s gems and one of the highest points on the island. In order to get to these gorgeous views of the eastern part of the island will have to hike alongside ravines, hike through tunnels, all while gaining and losing elevation. The Torres bypass and its stunning balconies takes us within stones throw of Pico Ruivo to the Ruivo refuge. Here we’ll have the option of quenching our thirst before a panoramic ascent of Ruivo, the island’s highest peak, weighing in at 6,106 feet (1862 m). This vantage point affords views of jagged ridges and rock masses poking up through the cloud banks. Descending the Achada do Texeira brings us to our hotel transfer to Santana, the largest village on Madeira’s North coast with its idyllic thatched roof cottages.

Day 6

  • Hiking Mileage: 7.5 miles (12 km)
  • Elevation Gain: 1312 ft (400 m)
  • Elevation Loss: 2953 ft (900 m)
  • Drive Time: 30 minutes

After a short vehicle transfer, we’ll start our hike to the lush and verdant Queïmadas. Today’s hike has us traversing a series of wide paths, narrow paths, and tunnels so don’t forget your headlamp! We’ll pass by the “green cauldron” or 100-meter waterfall that descends into a large basin. Our hike back will afford us spectacular views of the north cost villages of Sao Jorge to Santana. At this point we have a short vehicle transfer to our hotel in Santana.

Day 7

  • Hiking Mileage: 7.5 mi (12 km)
  • Elevation Gain: 2625 ft (800 m)
  • Elevation Loss: 3281 ft (1000 m)
  • Drive Time: 30 minutes

We save one of the most beautiful days for last as today we get to experience the stunning landscapes near Texeira. Here we’ll walk a path bordered by heather with stunning views of nearby peaks. In addition to the heather you’ll see til, laurel, and possibly Madeira blueberry. We’ll hike to Torrinhas pass, Curral da Freias, Boaventra, Encumeada pass, and finally the Paul da Serra plateau with its monstrous wind turbines. Our day ends with a transfer to Funchal and a celebratory dinner.

Day 8

  • Shuttle: 30 minutes

Today marks the end of our adventure together. We’ll conclude with enjoying one final Madeiran breakfast together and then depart for a short 30-minute private shuttle to the airport. Thank you for choosing Wildland!


2025 Itinerary Updates

2025 Itinerary Update: For any departures in 2025, we will experience all of the same great hikes, but we have rearranged the itinerary. We will send nights 1 and 2 in Funchal and will have one fewer night in Santana.

Porto Moniz Add-On Package

Looking to explore even more of Madeira? We have you covered with a 1 night/2 day, 4-star lodging package that includes admission to the world-renowned Porto Moniz lava pools. With private transfer to/from Funchal and Porto Moniz and your hand-selected accommodations booked for you, you’ll have time to relax and enjoy an exquisite piece of the North island. Click here to read more about our Porto Moniz Add-On Package!


Please Note: We always do everything in our power to follow the set itinerary, however occasionally trips are subject to itinerary changes based on a variety of circumstances, including but not limited to: lodging/campground availability, extreme weather, political or bureaucratic obstacles, earthquakes, fires, flooding, changing boat schedules, and more. Normal terms and conditions apply to trips with itinerary changes.


Trip Dates & Booking


Click on a date to register. You can also click here to request new dates or book through customer service.

Available to Book


This trip is available and bookable online! Click on the date to register now or contact us online to book through our award-winning customer service team!

Going Fast


This trip has 1 or 2 spots remaining and is bookable online! Click on the date to book now or contact us online to book through customer service.

Request a Reservation


This trip is exclusively booked through customer service due to logistics with lodging, permits, staffing, availability, or something else. Please contact us online or call us at 800-715-HIKE (4453) to request a reservation.

Don't see your dates? Call us! We may be able to add new trip dates.

800-715-HIKE (4453)

Trip Details

Trip Details

What's Included

  • A detailed trip packet that takes the guesswork out of your travel, training, packing, and preparing for the trip
  • Trained hiking guide(s) with years of personal wilderness and hiking experience, medical certifications, and a passion for leading people into breathtaking landscapes. See Guide Bios.
  • Lodging for the duration of the tour
  • Airport pick up and drop off (at designated times)
  • Transportation throughout trip via private transfer
  • All meals from Dinner Day 1 to breakfast on Day 8
  • Use of day pack and hiking poles
  • Emergency equipment including a company-issued first-aid kit and communication device

What's Not Included

  • Transportation to Funchal, Madeira
  • Trip insurance that includes medical coverage and at least $200,000 in evacuation and repatriation coverage (required)
  • All expenses due to unavoidable events e.g. flight cancellation, personal illness, strikes, etc. (we recommend trip insurance coverage for these variables)
  • Clothes, rain gear, and footwear (see recommendations) should have ankle support as terrain can be uneven.
  • Bar bills, drink bills, extra snacks, telephone bills, Wi-Fi bills and other personal expenses (shopping/laundry/spa or sauna)
  • Sunscreen, toiletries and personal items
  • Water bottles
  • Guide gratuities are optional and at the discretion of each customer. A suggested guideline is to reward outstanding service with a tip of 10-15% of the total trip cost. Please tip your lead guide and they will distribute responsibly to the crew. Local currency is preferred, or USD is also appreciated.

Click here to see a printable, downloadable trip information packet with more detailed guidance about what to pack.

Meals: What To Expect

Madeira’s cuisine is both rich and colorful drawing equally from its Portuguese and maritime roots. A variety of soups, grilled seafood, meat & fish stews, and grilled meats are sure to please your palette. Madeira’s specialty is the Espetada or brochette which is a beef skewer with a mixture of seasonings. Another specialty is the Prego Sandwich made up of thin slices of beef seasoned with garlic and served with sauteed onions on a bread roll.  Madeira is also known for cultivating wine and rum, which you can sample in its signature drink of Poncha.

We can often accommodate vegan, vegetarian and non-gluten diets and make adjustments for food allergies. These and other special dietary requests may require an additional fee, and in some countries may be more difficult to accommodate than others. Please inquire with us for more information about the specific trip you’re interested in.

Gear We Provide

We provide all group gear which includes the following:

  • Company-issued first-aid kit
  • Emergency Communication Device(s)
  • Trekking poles
  • Day pack

Guest Packing List

When you register for this tour you’ll receive access to a printable, downloadable trip information packet with a detailed packing list specific to this trip (click here to see it now.) All trips require a sturdy pair of hiking shoes or hiking boots, rain gear, a recommended clothing system, a headlamp or flashlight, a hydration system (water bottles and/or bladder) and other items specific to each trip.

Trip Logistics

Trip Logistics

How Do I Register?

Reserve your spot today! In the Trip Dates & Booking section of this page, the green and red dates are bookable online by simply clicking on the date, and blue dates must be booked through our customer service team for a variety of possible reasons. To email our customer service team, you can click here to get the ball rolling. Our adventure consultants will confirm availability, and if you’re ready to register we’ll email you a link to a registration profile. You’ll have 72 hours to complete your profile (and that of any dependents) and pay the deposit.

Feel free to call us for more info – we’re here 7 days a week!

Pre and Post-trip On Request Lodging

We secure limited amounts of pre and post trip lodging in Funchal as an optional add-on for guests of this trip. This lodging is on request, and is available on a first come, first serve basis. If interested, please reach out directly to our team to check availability.

We also provide a Porto Moniz Add-On package for this trip. This one-night package includes transfer to Porto Moniz, lodging, and breakfast. Please find more details here.


Where Do We Meet?

You will meet your guide at the Madeira Airport International Cristiano Ronaldo in Funchal on the first day of the trip. Please plan for your flight to arrive by 3 pm or earlier on Day 1.

Please note that we arrange for one included airport pickup at 2 pm. Should you require pickup at a different time, we can arrange for that for an additional fee.

For those who wish to arrive a day early, we recommend Castanheiro Boutique Hotel for enjoying Funchal. We may be able to arrange pre or post trip lodging upon request; please contact our Adventure Consultants directly to request.

Our Madeira communications team will be in contact via email approximately 45 days before your trip to coordinate and confirm your rendezvous and answer any last-minute questions you may have.

Travel To/From Funchal, Madeira


For this Madeira Trekking adventure, you will need to fly in and out of the Madeira Airport International Cristiano Ronaldo located in Funchal, the largest city on the island. Flights should arrive by 3 pm or earlier on Day 1. Your guide will pick you up at the airport on Day 1. If you’d prefer to get in a day or two early, we recommend Castanheiro Boutique Hotel for enjoying Funchal. We may be able to arrange pre or post trip lodging upon request; please contact our Adventure Consultants directly to request.

On the last day of the trip, guests will be transported to the Funchal Airport at about 2 pm. Departing flights should be planned no earlier than 12pm to utilize our provided airport transportation this day. Any airport transportation needs outside of this will be at the guest’s expense.

Flights to and from the Funchal airport are the guest’s responsibility. Multiple airlines operate flights into Funchal from many U.S. and European international airports. Some of the primary U.S. departure cities include Boston, Newark, New York, and Miami.

Safety Precautions

Your safety is our top priority. Our hiking tours are led by professional hiking guides, all of whom are wilderness-certified first responders or EMT’s, each with years of guiding and wilderness experience. Guides adhere to standardized risk management protocols in case of any potential or actual incident, and all tours carry an emergency communication device and comprehensive first-aid kit. Additionally we have a “24/7” system through which guides or guests can reach Wildland support personnel at any time.

In the interest of your safety, it’s important to refer to the Center for Disease Control website for up-to-date recommendations on immunizations before your trip.

Essential Eligibility Criteria

Essential Eligibility Criteria (“EEC”) have been specifically identified to help you understand the skills and abilities necessary to participate on each Wildland trip, and they apply uniformly to all potential trip participants, irrespective of the presence or absence of any disability.

Once you identify a trip in which you may be interested, please carefully review the EEC and itinerary details. If after reviewing the EEC that apply to your desired trip, you determine you need an accommodation in order to meet the EEC, please contact us prior to registering to discuss your requested accommodation.

The EEC exist for your own safety and the safety and enjoyment of all participants. If you are unable to meet the EEC for the trip, with or without an accommodation, you are not eligible for that trip. If you register and arrive for a trip for which you do not meet the EEC, you will be disqualified from participation on the trip and will be dismissed or evacuated from the trip without a refund.


Our approach to international travel is to combine the best of two worlds: the dialed-in details, professionalism, and consistency Wildland trips are known for; and the cultural immersion and intimate regional knowledge that only locals can provide. To excel with this approach, we vet and hire the best local guides, welcome them into the Wildland family and train them to meet our standard of excellence with every aspect of a trip. But along with managing logistics and safety, your guides will teach you about the area’s history and culture, and provide a level of familiarity and intimate detail only locals can.

Check out our Meet Our Team page for staff bios.

Guide Working Parameters

Guides are required to take 8 hours off each 24-hour period to sleep, recuperate, take personal/down time…etc. In addition, as part of the 8 hours off they must sleep/rest or be in their tents/rooms uninterrupted for a minimum of 5 hours each night. We ask guests to respect these requirements and to not interrupt guides’ off time and sleep time unless there is a true emergency.

Age Restrictions

Age restrictions on this trip are as follows:

  • 12 and older to join scheduled tours (mixed groups)

Trip Insurance

Field evacuation, repatriation, and medical insurance is required on this trip as a condition of partnership terms with our European vendors (field evacuation and repatriation minimum coverage is a combined $200,000 USD).

If you need to purchase field evacuation, repatriation, or medical insurance we recommend IMG/iTravelinsured. They are one of the world’s leading providers of travel insurance and policies meet all requirements.

For information on the recommended IMG/iTravelinsured policies please click here.

For even greater information, or if you simply prefer communicating with a real, live person, feel free to contact our exclusive agent Michael Bennett. Michael will help you identify the best product for your needs, and there is no cost associated with his assistance. You may contact him at:

Email: [email protected]
US by Phone: 877-305-9083
Direct/International by Phone: 702-448-3664

If you already have the required insurance or wish to purchase from anyone other than IMG/iTravelinsured, we recommend careful consultation with the provider to ensure appropriate coverage. This is because many providers have a number of policy exclusions.

Weather In Madeira

Madeira’s weather is consistent, pleasant, and generally quite mild. The island’s mountainous topography lends itself to many different and diverse microclimates. The sun shines brighter during the summer months but it is generally sunny and pleasant throughout the winter. This consistently nice weather makes Madeira a popular destination for travelers and surfers year-round.

In the summer you will find an average temperature of 75°F (24° C) to 80°F (27°C). In the cooler months expect a temperature of around 64°F (18° C). Be prepared to have some sun layers or sunscreen as well as a nice insulating layer for the evenings.




Castanheiro Boutique Hotel is located in the heart of historic Funchal. Here you’ll encounter a blend of detailed architecture, modern design, and a warm, welcoming atmosphere. This hotel boasts a lap pool, 81 rooms, pleasing views of the Bay of Funchal, as well as close proximity to shops, museums, restaurants, and bars. Buildings on this site range from 18th to 20th century and have housed a typography company and an embroidery company. The hotel includes period pieces, antique furniture, and other antiques that reflect the site’s history resulting in a unique and cultural experience in the heart of Funchal.


Hotel Portobay is located next to the Santo da Serra Golf Course, surrounded by nature with a traditional Madeiran atmosphere. The main house was restored in 1999 and originally built in 1920. The hotel’s garden has over 90 varieties of flowers and plants, clearly identified for the curious observer. The hotel also has multiple pools, both indoors and outdoors.

Hotel Colmo on Madeira Island, Portugal


Hotel Colmo on Madeira Island, Portugal

Hotel O Colmo is located in Santana’s city center on the north coast of Madeira Island. Here you’ll find traditional thatched roof cottages with beautiful views of both the mountains and ocean. O Colmo is located in a tranquil garden setting with views of both the mountains and ocean. This hotel also has a heated pool.

* These exact accommodations are not guaranteed. In some instances alternative accommodations of similar quality and location may be used.

Trip Reviews

Trip Reviews

  • Average Customer Ratings:

  • 5.0 (2 reviews)
Amanda M

Can’t wait to book my next Wildland tour.

3 months ago

Had a great time on this tour with our small group. The guides were both very helpful and knowledgeable and it was nice to be able to relax and have a nice dinner and warm shower after each of the hikes. They handled all the logistics so that it was truly stress free ( minus climbing up the mountains of course). The hikes were all beautiful, and the food on the hikes and at the included restaurants was all delicious. Can’t wait to book my next Wildland tour.

Scott K

Dynamic & Diverse

3 months ago

Great guides, fabulous food, scintillating scenery, dynamic & diverse destinations, and luxurious lodgings!

See All Guest Reviews!

Go to our reviews page

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