Ultimate Madeira overnight hiking experience

As part of this incredible GetYourGuide experience, a group of explorers hiked to Madeira’s highest point for uniquely spectacular views with travel adventure photographer Jackson Groves and a local expert.

The guide led hikers through the world-famous Pico Ruivo to Pico do Arieiro route, along narrow paths, twisting tunnels and up stone staircases. A challenging trek, sheer drop-offs, and an overnight stay in a local mountain hut made this one of the most unforgettable overnight adventures on the Portuguese island of Madeira.

Explore Jackson Groves’ favorite unforgettable experiences in Madeira below

About Jackson Groves

I’m Jackson, an Australian adventure traveler who has been on the road for eight years now. After graduating with a journalism degree, I set off to explore the world while creating adventure travel guides featuring hikes, waterfalls, beaches, and adrenaline activities. I’ve been creating travel guides for my blog for eight years and it’s been a road to freedom for me. I was able to create a living while simultaneously helping people explore natural attractions and offbeat locations around the world.

I’m still currently nomadic and travel with all of my possessions! I don’t have any milestones and usually go with the flow of life. I pair that with my determined and consistent nature to pour my heart and soul into whatever project I’m currently involved in.

Jackson, your adventures always seem epic, what do you look for when planning something to do?

I am always looking for a challenge first and foremost. I want my adventures to provide me with some tough moments but also some great views as well. When you can combine those two together, you are on a rewarding journey by pushing your body to its limits while enjoying the scenery.

How experienced are you with the Pico to Pico trail (first time, how many, different routes) and what made you want to share it with others?

The Pico to Pico trail is one of the most famous trails in Madeira. I’ve done this trail countless times and even guided a group across it before. We will be taking a back way up to the Pico Ruivo hut where I have stayed before and then taking the trail from Pico Ruivo to Pico do Arieiro the next morning. On day one we will have about 1,200 meters of incline to reach the hut across 10 kilometers from Encumeada. On day two we will have about 500 meters of incline from Pico Ruivo to Pico do Arieiro.

Who is this experience for, are there any enlightening moments that they might discover during the hike?

This experience is for local Madeirans who have probably never experienced staying overnight at the hut and who want to attempt a likely strenuous hike. It’s also for those from mainland Portugal who want to experience the best of Madeira in just two days. Finally, if there are some international visitors who are planning a trip to Madeira, wouldn’t this be a great way to start it? In addition to the hike, we will have our local guide, Joao, who will help provide us with some great local, traditional foods along the way. Expect a homemade poncha brewing session at the mountain hut in front of the wood fire!

Is it challenging? How does it compare to other hikes you’ve done?

This hike will be challenging but manageable. It will be a slow and steady approach. The hike up to Pico Ruivo is steep with about 1200 meters of incline over 10 kilometers. If you are in decent hiking shape or fitness, you will make it through. The hike the following morning is just six kilometers but also with 500 meters of incline up the famous stairways of Madeira. If hikers can manage those inclines, they will be fine.

You’ve lived in some of the most exciting places in the world, what makes Madeira special to you? What does Madeira have to offer that not many people think of from “Portugal”?

Madeira has a unique history with pathways winding all throughout its stunning mountain ranges and forests. It’s made for exploring. The local culture is strong with amazing traditional cuisines found across the island. The local seafood, the famous poncha alcoholic beverage, and the espetada steak are just the tip of the iceberg when it comes to delving into the rich culture of Madeira.

What are your top tips for someone considering this experience (not necessarily with you, what advice would you give someone)?

Prepare by trying easier, shorter trails with less incline to see if your body is up for the challenge. Bring enough water and snacks as well as rain gear in case the weather changes. If you are planning to stay overnight at the hut, book in advance [the stay is included if you book this experience].

What are you excited to share about the experience, or see the reactions of people (certain views, food, etc)?

This is one of the most mind blowing hikes in the world and I’m sure all of our participants will be amazed. Combine these hikes with our unique overnight stay at the mountain hut and it will be a trip to remember!

After the hike, returning to Funchal must be quite a contrast from the heights of the trail. What do you love about the city?

Funchal is a vibrant, historic port city with lots to explore. There’s nothing like wandering the streets of Funchal on a sunny day. The outside dining and small bars and restaurants have those quintessential European summer vibes.