Included: 8-day self-guided Best of Madeira hiking tour (with 5 days of hiking and 1 day off for light walking and sightseeing in Funchal) Accommodation for 7 nights in stunning 3 and 4-star hotels (ensuite double occupancy standard rooms) 6 breakfasts All transfers indicated in the itinerary, including taxi transfers to/from hiking locations every day Luggage transfers from accommodation to accommodation Numeric roadbook with detailed maps, vouchers, and contacts Emergency assistance 24/7 From 01/01/2025 to 30/10/2025, entry tickets for trails PR8, PR9, and PR10 Not included: Flights to and from Portugal/Madeira Tourist tax (€1 to €4 per night, per person) Drinks Meals not indicated in the itinerary Personal purchases Guide gratuities — optional Insurance — available to add at checkout

How fit do I need to be?

This self-guided hiking tour of the best of Madeira is rated moderate . A reasonable level of fitness is required, so you can expect to be hiking about 14 km / 8.7 mi almost every walking day. Check out the itinerary for day-by-day distances and elevation changes. For more hiking adventures in Portugal, click here !

What do I need to bring?

Here’s a list of the equipment you need to bring: Duffel bag to pack all of the things you need for the tour Day pack large enough to carry all the items listed (around a 25-40L bag) Hiking poles — optional Water bottle or hydration bladder (2L capacity) Lightweight hiking boots or shoes Comfortable hiking clothes Spare clothes for layering Clothes and shoes for everyday activities and restaurant Waterproof rain jacket Sunhat Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.) Headlamp or flashlight Sunglasses Camera — optional (but recommended) Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

What is a self-guided tour?

Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this best of Madeira self-guided hiking tour , we take care of charming accommodation in 3 and 4-star hotels, all breakfasts, all necessary transfers as in the itinerary, luggage transfers, and a numeric roadbook with detailed maps, vouchers, and contacts. You’ll also have emergency assistance 24/7 available. Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option! As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.

Group sizes and age requirements

Group sizes and pricing It takes a minimum of 2 people for this tour to operate. The maximum group size is set at 20 participants. Hiking in Portugal can be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Minors from 15 to 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian. If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

Getting there and meeting location

The starting point of your best of Madeira hiking tour is Santo Antonio da Serra. To get there, most people fly into Madeira Airport (a.k.a. Funchal Airport). Once you’re there, a taxi will transfer you to your accommodation in Santo Antonio da Serra.

Safety measures and insurance

We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout. Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

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MADEIRA | PORTUGAL

Self-Guided Hiking Tour: Best of Madeira

8 days | Moderate | 5.00

From $2,220 ()

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On this self-guided Madeira hiking tour, the only guide you need is your sense of wonder. Explore stunning basalt cliffs, ancient laurel forests, and levadas, typical Portuguese irrigation canals that feel like they belong in a fantasy novel. With no group to pace yourself against, you’ll have time to enjoy the views and the stories carved into this island’s landscapes. Discover villages steeped in tradition, hike cliffside trails with Atlantic views, and end it all with a splash of Funchal’s charm and maybe a wicker sledge ride—because walking isn’t the only way downhill.

Adventure Highlights

Madeira, your way: Explore at your own pace, with nature and culture in perfect harmony
A walk in the clouds: Hike trails with sky-high views and endless Atlantic horizons
Lush laurel forests: Step into UNESCO-protected laurel forests that feel like another world

Duration

8 days

Season

Year-round

Group size

Up to 20 people

Self-guided adventure

Accommodation, breakfasts, transfers, detailed roadbook, and support arranged

The adventure, day by day

Download itineraries

Embark on a hiking adventure across Madeira, where dramatic cliffs meet lush forests and history-rich trails. This self-guided tour gives you the freedom to explore at your own pace, following well-marked paths through some of the island’s most stunning landscapes. Walk alongside historic levadas, marvel at the UNESCO-recognized laurel forests, and take in sweeping ocean views from scenic vantage points. Along the way, you’ll encounter charming villages and terraced fields that showcase Madeira’s traditional way of life. With comfortable accommodations, daily breakfasts, and expertly designed routes, this trip offers a perfect blend of active exploration, cultural immersion, and breathtaking natural beauty—all without the constraints of a group tour.

Day 1: Welcome to Madeira

You will be welcomed at the airport and a taxi will transfer you to Santo Antonio da Serra, a typical village known for its market. Depending on your time of arrival, please feel free to wander in the village or enjoy the garden and swimming pool in your accommodation.

Accommodation: 4-star hotel

Day 2: PR8 São Lourenço peninsula

In the morning, transfer to the Peninsula of Sao Lourenço, located to the east of the island. The landscape is very different from the rest of the island because of the semi-arid climate and its basalt cliffs carved by wind and waves. This nature reserve allows you to observe the unique flora and fauna of the island. Return to your accommodation.

Meals: Breakfast
Hiking: 7 km / 4.3 mi, 3h
Elevation: 400 m / 1,312 ft
Accommodation: 4-star hotel

Day 3: Levada do Castelejo

Take a transfer to one of the most rural areas of Madeira and start your hike. Between the orchid-draped houses, you can marvel at the unique terraced crops that are traditional in Madeira, and many farmers still work the land manually. You will then enter the natural temple of the Laurissilva (laurel forest), following a levada that gradually enters the deep valley. You’ll then return via ancient and restored paths to the village of São Roque do Faial.

Meals: Breakfast
Hiking: 14 km / 8.7 mi, 4h50
Elevation: 400 m / 1,312 ft
Accommodation: 4-star hotel

Day 4: Boca do Risco balconies

You’ll transfer to the Tunnel of Caniçal in order to experience one of the most beautiful walks of Madeira on a footpath high above the ocean. After the terraced pastures of the Ribeira Seca valley, the coastal path of Boca do Risco gives you a high-angle view of the backwash and creaks below, and ends with a big descent to the ocean and to the fishermen’s village of Porto da Cruz.

Meals: Breakfast
Hiking: 13 km / 8 mi, 4h15
Elevation: +250 m / +820 ft, -350 m / -1,148 ft
Accommodation: 3-star hotel

Day 5: PR9 Caldeiro Verde

On Day 5, you’ll transfer to the start of your walk, where you will discover one of the most spectacular Levada hikes of Madeira. You will enter the famous Laurisilva laurel forest. After passing through several tunnels and (safe) cliffside passageways, you will get to the famous “Green Cauldron”, also known as Caldeiro Verde. Then, you will go back on the path to start walking down to the isolated village of Ilha, with incredible vantage points over the ocean. Later on, there’s a return transfer to Boa Ventura.

Meals: Breakfast
Hiking: 14 km / 8.7 mi, 4h30
Elevation: +90 m / +295 ft, -600 m / -1,968 ft
Accommodation: 3-star hotel

Day 6: Levada do Furado

Take a transfer in the morning. After hiking for a bit on a regular path, you’ll arrive at the levada do Furado, which you’ll follow for over 8 km / 5 mi. The famous levadas, small irrigation canals that are typical of Madeira, are located on the mountainside and are punctuated by waterfalls and views of the valleys, leading you through the laurisilva laurel forest. The first part of the Levada do Furado is spectacular, cut into the rock with safety barriers. Arriving at Ribeiro Frio, a short walk along the levada will give you fantastic views over the highest peaks of the island.

Meals: Breakfast
Hiking: 13.5 km / , 5h15
Elevation: +600 m / +1,968 ft, -365 m / -1,197 ft
Accommodation: 4-star hotel

Day 7: Funchal

Day 7 is reserved for sightseeing around Funchal, a charming city built like an amphitheatre around the bay. The city’s name originates from the word fennel (foncho in Portuguese) that grew in the bay when the Portuguese first landed here. It’s great to wander through the paved streets, colorful gardens, and walkways along the coast.

If desired, today you can do a few optional activities that are to be paid on site, such as visiting the Monte palace tropical gardens, which are accessible via a cable car, and you’ll get a panoramic view of the city. The other option is to go down from Monte to Funchal center on a traditional wicker sledge called “Carreiro do Monte”. The sledge is used by locals as a quick way of getting to Funchal.

Meals: Breakfast
Accommodation: 4-star hotel

Day 8: Departure

Today is the last day of your self-guided hiking tour of Madeira. Approximately 2h30min before the flight, there’s a taxi transport arranged to transfer you to the Madeira airport.

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Food and accommodation

Accommodation

On the Best of Madeira hiking tour, you’ll spend 3 nights at the Porto Bay Serra Golf in Santo da Serra (4 stars), 2 nights at the hotel Boaventura in Boaventura (3 stars), and 2 nights at the hotel Caju in Funchal (4 stars).

All three hotels offer a unique stay in Madeira with a shared focus on comfort, charm, and thoughtful amenities. Each features delicious breakfast, cozy rooms, and easy access to nature or city life, while some also offer indoor pools, tranquil garden spaces, upscale restaurants, and more! Whether you’re after mountain serenity, lush forest surroundings, or downtown flair, they all provide warm hospitality, local character, and the perfect base to relax after a day exploring the island

Food

All breakfasts are included in the price of this self-guided hiking tour of Madeira. The most common items that can be found on a Portuguese breakfast table include bread, ham, cheese, sandwiches, fruit jams, sweet breads such as pão de Deus, and coffee with milk. And of course, there’s always a chance to get the famous Portuguese pastel de nata custard tarts.

Adventure, packed to go

Self-Guided Hiking Tour: Best of Madeira

Adventure Brochure

Brochure and video trailer

Download the trip brochure and cinematic trailer—everything you need to plan, share, or start dreaming.

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What others say about this adventure

5.00 (5 reviews)

Jagat N.

|October 2025

Everything was planned out so well. I liked not having to worry about the day to day logistics and just worry about enjoying the trip, my walks and carrying my day pack.

John S.

|May 2025

Madeira’s hikes are spectacular.

Lisa W.

|May 2025

Madeira Island provided a perfect balance of adventure and free time. All the hikes we're beautiful, each in a different way. The challenges were moderate but nothing too strenuous. Some were very crowded and I recommend asking for earlier pick ups if you don't mind that. Each lodging location was beautiful and unique, but some were pretty remote. Plan to eat in the hotels which have fabulous food, full bars, and nice pools. Overall a fabulous adventure as described.

Show all reviews

Jagat N.

|October 2025

Everything was planned out so well. I liked not having to worry about the day to day logistics and just worry about enjoying the trip, my walks and carrying my day pack.

John S.

|May 2025

Madeira’s hikes are spectacular.

Lisa W.

|May 2025

Martha Schrader

One of our most memorable trips with our kids.

Bastien Serafin

Very professional service coupled with great customer care.

Things to know

Included:
- - 8-day self-guided Best of Madeira hiking tour (with 5 days of hiking and 1 day off for light walking and sightseeing in Funchal)
  - Accommodation for 7 nights in stunning 3 and 4-star hotels (ensuite double occupancy standard rooms)
  - 6 breakfasts
  - All transfers indicated in the itinerary, including taxi transfers to/from hiking locations every day
  - Luggage transfers from accommodation to accommodation
  - Numeric roadbook with detailed maps, vouchers, and contacts
  - Emergency assistance 24/7
  - From 01/01/2025 to 30/10/2025, entry tickets for trails PR8, PR9, and PR10
Not included:
- - Flights to and from Portugal/Madeira
  - Tourist tax (€1 to €4 per night, per person)
  - Drinks
  - Meals not indicated in the itinerary
  - Personal purchases
  - Guide gratuities — optional
  - Insurance — available to add at checkout
This self-guided hiking tour of the best of Madeira is rated moderate. A reasonable level of fitness is required, so you can expect to be hiking about 14 km / 8.7 mi almost every walking day. Check out the itinerary for day-by-day distances and elevation changes.

For more hiking adventures in Portugal, click here!
Here’s a list of the equipment you need to bring:
- - Duffel bag to pack all of the things you need for the tour
  - Day pack large enough to carry all the items listed (around a 25-40L bag)
  - Hiking poles — optional
  - Water bottle or hydration bladder (2L capacity)
  - Lightweight hiking boots or shoes
  - Comfortable hiking clothes
  - Spare clothes for layering
  - Clothes and shoes for everyday activities and restaurant
  - Waterproof rain jacket
  - Sunhat
  - Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
  - Headlamp or flashlight
  - Sunglasses
  - Camera — optional (but recommended)
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this best of Madeira self-guided hiking tour , we take care of charming accommodation in 3 and 4-star hotels, all breakfasts, all necessary transfers as in the itinerary, luggage transfers, and a numeric roadbook with detailed maps, vouchers, and contacts. You’ll also have emergency assistance 24/7 available.

Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!

As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.
Group sizes and pricing
- - It takes a minimum of 2 people for this tour to operate. The maximum group size is set at 20 participants.
Hiking in Portugal can be arranged for larger groups. Contact us to make arrangements.

Min. age requirements
- - If you are older than 18, you’re good to go.
  - Minors from 15 to 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.
If your group has hikers under the age of 18, contact us prior to booking to make arrangements.
The starting point of your best of Madeira hiking tour is Santo Antonio da Serra. To get there, most people fly into Madeira Airport (a.k.a. Funchal Airport).

Once you’re there, a taxi will transfer you to your accommodation in Santo Antonio da Serra.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Deposits
You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

Cancellations
Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:

Basic
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
  - For cancellations 0-59 days before the trip, there is no refund.
Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
  - For cancellations 0-29 days before the trip, there is no refund.
Super Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.

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