The Ultimate Fall Escape in Portugal: Madeira Island RoundTrip

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Guided trip
What's special?
special Top Hikes
special Travelling with location expert
special Unique nature spots
Fall is already here and you really want to escape the cold and gloomy weather? You are not the one to sit on the beach and do nothing, you seek adventure and to explore beautiful nature, then this trip is exactly for you! Come join me for this eye-widening trip to an island full of colors and magical energies, Madeira. Sunrise over the ocean or on top of the highest mountain, beautiful hiking paths, getting lost in a mystical forest, enjoying vibrant capital city vibes and local food, chill on the coast and settling our mind during sunsets, and much, much more. Check the full itinerary to know more! :) There will be some fruits, oats, coffee and tea in the house, for bigger meals I would suggest we do some cooking together or explore local cuisine outside at our own expense. The price includes: - Accommodation (shared house - private bedroom) - Car rental - Petrol expenses - Location Expert Let’s take advantage of this Hawaii of Europe to the maximum, we will enjoy all the variety of the flora in different parts of the island and also the vibrant capital, Funchal. Do you have a question? Ask in the Q&A below! Welcome to Madeira and looking forward to hearing from you! 🙌🏻

I'm a passionate traveler, currently on a mission to spread happiness in the world, the joy in mind & body via exploring different cultures and connecting to other like-minded beings. Since I stayed in Madeira for the first time in 2021 I am absolutely obsessed with the energy of this island. I would like to introduce it to you in my eyes. Are you looking to explore yourself, connect to nature, and explore not-so-touristy places on the island? Let’s do it together!

We will share a nice 3-bedroom house together. The house has 3 separate bedrooms with double beds and 2 bathrooms, located in Machico, a lovely coastal town in a picturesque valley. Some of us will have a private room, some share a room with other trip mate. We will have a car to explore the whole island during our stay, but this will be our home for the whole duration.

What's included?
Car + Fuel (&driver :))
Top Hikes
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Open minded ocean-kid, yoga lover & passionate traveller, currently on a mission to spread happiness in the world via travelling.

5 based on 32 reviews


Gabi is an amazing person and very great trip leader. We spent an amazing week together in Madeira and discovered the island at its fullest, through a variety of cool activities, like hiking-surfing and a magical joga experience. Also she showed us all hidden gems of this magical place. If you are planning a trip to Madeira Gabi is definitely your go to! 🩵🧜🏼‍♀️
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You can chat with Gabriela once you reserve your spot.
Trip Itinerary


Day 1-2
I will take care of you on the first day, (Day 0) since you arrive at the airport. I will be in Madeira earlier, so I will make sure to pick you up! We will take it easy, gather everyone and get to know each other. Our shared accommodation is located close to Machico, a lovely coastal town in a picturesque valley. The house have multiple balconies with stunning views, big enough common area and great internet connection. Machico offers everything you could imagine in a town, but also a great, lovely community of digital nomads and expats. Car costs are included in the price of the trip, and I really enjoy driving, so additionally you will have your personal driver haha :)

PR8 Verada da Ponta de São Lourenço

Day 2-3
Our first full day all together on the island, we will start strong with a sunrise hike in Ponta de São Lourenço. Even though this is one of the most popular hiking paths on the island (for a good reason!), we will beat the main tourist wave by starting early. Watching the sunrise over the ocean with the peninsula in front of us will give us a good enough boost for the day! After we complete this hike, there is a sweet reward waiting for us on the way back, we will dip in the Atlantic Ocean & relax on a cute little black sand beach.

Levada Nova

Day 3
The Next day we will do a beautiful Levada Nova. Stunning views, an exciting tunnel, and a mesmerizing waterfall. All that plus breathtaking nature all around us. (Hike location is subject to change based on the weather forecast or mood of the group, we can change the choice of the trail if we like, there are too many options in Madeira!)


Day 3-4
Time to visit Funchal, the capital of Madeira. We will visit places like Santa Catarina Park with awesome views of Funchal and the harbor with cruise ships, Funchal promenade, an old town with cute painted doors and lots of local food restaurants, the famous Poncha bar, and much more.

Achadas da Cruz

Day 4
Another day, another fun thing to explore. On the West Coast, there is my favorite and also the steepest Cable Car ride in Europe, which will take us to Achadas da Cruz, down to the ocean, a light walk with stunning views.


Day 4-5
A day of exploring and relaxing will continue with some time to connect with the water element and the powerful ocean. We will go explore the north coastal villages of Seixal and Porto Moniz, Seixal is famous for its Black sand beach with stunning views of the cliffs, and Porto Moniz with its volcanic pools.

Pico do Arieiro

Day 5-6
Another sunrise hike is awaiting us! This one definitely cannot be missed when you're in Madeira. PR1 from Pico do Ariero to Pico Ruivo (the highest peak) is famous for its stunning views and would be a shame to miss it. We will start at sunrise to get the most out of it, cause watching the sunrise over the clouds below us is an unforgettable memory. * In case someone is not feeling like doing Pico to Pico, there is an option to do PR 1.2 instead to reach the highest peak of Madeira that way :) All plans are open to suggestions and discussion based on needs and weather conditions!

Levada dos Balcões

Day 6-7
Free DAY This day I am keeping open for discussion, there are simply a lot of options for what we can see & do. Options include, but are not limited to : a/ Easy day on a beach where we can do Yoga together, have a picnic, chat, or read our favorite book. b/ Active day, choosing a trail to do and simply go for it and then reward ourselves with Poncha! c/ Experience day, booking a surf lesson or Canyoning and pushing our limits d/ Road trip day, want to see as much as possible, do you still have a list of places you want to tick off? Let's drive around the island in a day.

PR13 Vereda do Fanal

Day 7
On our last full day together, we will start by visiting the mystical Fanal forest. It is a truly magical place, mysterious fog usually covers the evergreen trees, and it is just like in a fairy tale. Small hike around and time for unique pictures.

Ponta do Pargo

Day 7-8
On our last night together, we will reflect on the amazing trip, whilst watching the sunset at the west point of the island. One of the top sunset viewing spots next to the lighthouse, perfect to watch the sun setting on the horizon.

Santa Cruz

Day 8-9
On the last day (Day 9), the departure day, if the timing of your flights allows, we will visit the best viewing point to see the spectacular aircraft landings at Madeira Airport. In the end, I will drop you at the airport and we will say our farewells! :)
Trip Summary
9 days trip
Machico, PR8 Verada da Ponta de São Lourenço & 9 more
Questions and Answers

Hello Gabriela, if there is still a free place on your trip at short notice, please get in touch :)

Hello! Will do! In case you can travel beginning of December I do have another trip with spots available! :)

Hi Gabi, I'm interested in your trip from 18.11. Can you please also send me photos of the accommod... Read More

Yes of course, happy to! Let's chat!

Hi Gabriella, sounds great! I looked for a flight and on 18.11. I can arrive at 22.15 in Funchal wit... Read More

Of course Susanne, you will be picked up at any time based on your arrival, that's not problem at all! Looking forward to have you on board! ✈️🩵

What's excluded?
International Flights
Main meals
Additional activities
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