Hiking the Islands | The Azores & Madeira

Hiking the heavenly trails of São Miguel and Madeira Islands.

We created a fun-filled hiking itinerary to help you make the most of your experience in Portugal’s Islands! 

What's Included?

All flights and connections
Accommodations for your destinations
Airport-Hotel Transfers
Walking Tours: Serra Devassa + Boca do Inferno & Sete Cidades
Walking Tours: Sanguinho Salto do Prego Waterfall + Furnas
Hiking: Rabaçal / 25 Fontes Levada Walk
Expert trip manager
All taxes & fees

Why we love this deal:

  • This is the perfect escape for those who enjoy hiking amid nature and discovering hidden gems! 
  • The Azores Islands and Madeira are world-class destinations for adrenaline seekers and nature lovers alike, and the best way to truly discover all the hidden gems around the archipelagos is by hiking. Included in this exciting offer are the following tours:
  • Levada do Rabaçal - 25 Fontes (Madeira Island): With its many gorgeous mountains and waterfalls, it’s no surprise that Madeira has long been referred to as a “hiker’s paradise”. Many of these trails follow the old irrigation canals called “levadas” that were used to bring water from the north side of the island to the south.
  • Salto do Prego Hiking Trail & Van Tour to Furnas (São Miguel Island): Combine the adventure of one of the most beautiful hikes in São Miguel Island with a comfortable van tour to Furnas – all in one experience! 
  • A Sete Cidades Hiking Trail + Tour (São Miguel): There are (amazingly) 11 lakes in total around Sete Cidades, but they can only be seen from certain angles at the different miradouros (viewpoints) in the area. To fully appreciate the breathtaking panoramic views over the mystical blue and green lakes, head to the Vista do Rei viewpoint.  While you're there, make your way over to the Boca do Inferno to enjoy some jaw-dropping 360 views overlooking the Lagoa do Canário and other lagoons below, Sete Cidades village, and an expansive view of the Atlantic Ocean beyond the ridge of the crater.
  • Customizable: Add more nights to your stay, a rental car or even more local excursions!


Day 1
Arrival to Madeira Island

 It is recommended to book airport transfers (or to get a rental car) and an early check-in.

Suggestion for the day:

  • Take the afternoon to stroll around Funchal’s historical streets and gardens. 


  • Monte Palace Tropical Garden
  • Madeira Botanical Garden
  • Funchal Cable Car
  • Church of Nossa Senhora do Monte
  • Monte Toboggan Ride
  • São Tiago Fortress
  • Mercado dos Lavradores

Or book here your Food & Wine walking tour of Funchal. Another alternative is to combine a jeep expedition with a short hike (book here).

With its many gorgeous mountains and waterfalls, it’s no surprise that Madeira has long been referred to as a “hiker’s paradise”. Many of these trails follow the old irrigation canals called “levadas” that were used to bring water from the north side of the island to the south.

Suggestion for the day:

  • Discover Madeira’s Eastern wonders


  • Santana
  • Machico
  • Pico do Arieiro
  • Ponta de São Lourenço 

Or book here your full-day guided tour. Another suggestion is to combine a boat trip with a jeep tour (book here).

Suggestion for the day:

  • Take the day to explore Madeira’s food & wine scene: Situated in the Atlantic between Portugal and the coast of Morocco, Madeira is in a unique location at the intersection of many different flavors and influences. What can you expect to find on the menu here? Fresh tuna steak, fried cornmeal, kabobs, breads, mackerel, octopus, homemade couscous, wheat soup, and of course, loads of fresh fruit and delicious Madeira wine! 

Recommended experiences:

It is recommended to book an early check-in and airport transfers (or to get a car rental)  in the Azores as well.

Suggestion for the day:

  • Take the afternoon to stroll around Ponta Delgada’s city streets. Ponta Delgada, the main city, is not only the hub of the island but the capital of the Azores. Ponta Delgada evokes all the charms of Europe with cobbled streets, sidewalk cafes, and a thriving culinary scene. Or book here your Ponta Delgada City Tour. 

Not to miss:

  • Portas da Cidade
  • Louvre Michaelense
  • Pineapple Plantations
  • Matriz Church


Embark on a whale and dolphin-watching experience.

The Azores Islands are known for their unparalleled beauty and biodiversity, adored by outdoor adventure enthusiasts and nature lovers alike. But what people may not know is that the Azores is also one of the fastest-growing whale-watching destinations in the world. Located in the Atlantic Ocean between Portugal and North America, the Azores are a permanent home and natural point of passage to more than 20 different types of whale and dolphin species, making the islands one of the world’s largest whale sanctuaries. Book here


The Azores are a world-class destination for adrenaline seekers and nature lovers alike, and the best way to truly discover all the hidden gems around the islands is by hiking. Whether you book an official Azores hiking tour with a knowledgeable local guide or decide to hit the trails for an adventure on your own, the Azores offer more than 60 hiking trails awaiting to welcome you, all of which have great conditions for walking safely. 

One of São Miguel Island's best hiking trails is the Sanguinho Trail in Faial da Terra - one of the island's most remote and unpopulated places. Faial da Terra is a sparsely populated, magical little village that is host to one of the Azores' most heavenly hidden gems. During the hike, you’ll have the opportunity to appreciate the rustic charm of the old village houses and fruit orchards that can be seen from the trail, offering scenic beauty and harkening back to a simpler time.

*itinerary presented is a suggestion and the length of stay may vary. All tours are suggestions unless specifically stated.

Flexibility Policy

No Amendment Fees on Our End
We don’t charge for our work in changing the initial itinerary.
Full flexibility on Land Arrangements
Change the initial itinerary or cancel your land arrangements for any reason until 14 days before the trip, without penalty.
Support 7 Days a Week
Our experienced travel agents are are available 7 days a week (16 hours per day) to help with any questions.

About the Destination:

The Azores

Venture out and breathe in the pure Azores air as you explore lush forests and ravines. Wave hello to the friendly local cows roaming free as you walk across the green patchwork countryside. Admire the reflection of the beautiful blue lakes and emerald lagoons as you hike around volcanic landscapes, and lift your face to be swept by the salty sea breeze as you pass through UNESCO-protected vineyards on your way down to the coast. All of this, and more, awaits you in every single hiking adventure in the Azores.

The Azores Islands have an excellent network of trails that allow you to explore their most pristine and unspoiled locales on foot. Imagine hiking on vibrant green and verdant nature paths, discovering awe-inspiring waterfalls and taking spectacular photographs of stunning landscapes, all while breathing in the fresh, clean air of the Azores. Now pack your bags, because these paradise imaginings are real, and they are waiting in the Azores!

Check out our Azores Travel Guide for more information and tips.


If hiking and getting out into nature is your idea of an ideal vacation, Madeira is the perfect destination for your next jaunt. The fact that Madeira boasts mild weather and equally mild ocean temperatures year-round only adds to its appeal for hikers, and for anyone looking to experience adventures and the island’s stunning natural beauty, by land or by sea.

Imagine getting out into the great outdoors - hiking, or even biking, through the island’s extensive natural reserve and discovering stunning coastal cliffs with mesmerizing views, cascading waterfalls, and lush laurel forests protected by UNESCO! You can even supplement your hiking adventures with other amazing experiences, like exploring the surrounding seas by kayak, sailboat, jet-ski, or surfboard, or discovering what lies beneath these pristine blue waters with a snorkel or scuba diving excursion! All of that adventurous fun, and more, awaits in sunny Madeira.

Check out our Madeira Travel Guide for more information and tips.

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