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Madeira Crossing – Trail Running Adventure

£850 pp

Madeira, Portugal

7 days


Madeira Crossing – Trail Running Adventure

What You'll Do

A perfect balance of epic runs and relaxation. Combining technical terrain and high peaks with Laurel forest this trail running journey has it all.

This trip runs 23rd – 29th October 2021

Madeira, an island praised for its inclement weather, nature reserves and irrigation system (levadas). The island has a lot to offer when it comes to trail running, and we’ve found the most beautiful trails on the island. This retreat has a perfect balance of epic runs and relaxation, where it’s just as much about the journey and experience. Not only is it an active well-balanced holiday, it offers true trail running exploration, combining technical terrain and high peaks with Laurel forest.

A retreat like this is a great opportunity to meet like-minded people, share stories and enjoy the beautiful landscape. It’s about running wild and relaxing in amazing landscapes with a small group of like-minded folk. By combining our runs with stretching, nourishing food and rest, we take an holistic outlook on trail running. During the retreat, guests are encouraged to listen to their body and set their own pace.

So what are you waiting for? It’s time to get off the beaten track, into the mountains, and away from the hustle and bustle of everyday life. We move as one, embrace nature and all it has to offer, from the valley floor to mountain top and everything in between. If you’re looking for a stunning place to rest and rejuvenate, this is it.

Please note that the twin rooms are booked on the basis of two sharing. A single supplement is available on an enquiry basis.



4 carefully curated guided trail runs. Designed by runners for runners

Unique villa style accommodation

Stretch and strength classes to supplement your running

Enjoy nutritious home-cooked food

Your Local Host:

Ruth and Kerran

As a team of experienced runners, practitioners and health enthusiasts, the Running Team aims to provide the perfect balance of activity, relaxation and fun. Ruth and Kerran organise fantastic running breaks in amazing places. Using his experience as a long distance runner and outdoor adventurer, Kerran carefully plans and tests each trail, sele Read More

Experience Itinerary

Arrival day

Today you arrive at Funchal airport and make your own way to the villa in Sao Vincente. The most convenient way to is to hire a car which you can easily do from the airport or it is a scenic 1-hour taxi ride. Renting a car allows you the freedom to explore the island after you have finished your days running, there is so much to see it would be a shame to miss it. Tonight, you meet the crew and fellow runners during an evening meal.

Meals included: Dinner

Madeira running

Up early for a hearty breakfast, we warm-up, stretch and run through a final kit check before taking a short transfer to the trail head to set out on our first proper run (approx. 4-5hrs). Starting in Ribeira da Janela, we make our way along Madeira’s famous irrigation channels (levadas) and through Laurel forest before finishing with a dip in the natural sea-pools of Seixal. We then transfer back to our base for a simple yet tasty lunch, with the afternoon free for relaxing or exploring. We all reconvene for dinner at the villa.

Meals included: Breakfast, lunch and dinner

Madeira running

Today we are starting our trail run in the same town as we finished the previous day. We follow the trail with a consistent and gentle climb to Pico Ruivo do Paul, the highest point of the day. But it isn’t all running today, we also stop to take in the spectacular views before descending again through a protected forest. The descent is as gentle as the incline before heading back for lunch at the villa, followed by an optional 30-45-minute stretch and strengthen session or yoga class. The rest of the day is free to explore before dinner.

Meals included: Breakfast, lunch and dinner

Madeira running

Today is a rest day as we don’t want you to peak too soon. Breakfast is served at the villa but the remainder of the day is yours to explore the island or just unwind closer to base. Lunch and dinner today are not included but there are several options in Sao Vicente and other towns along the coast.

Meals included: Breakfast

Madeira running

Heading out from the accommodation we make a short (15 minute) transfer to our start point, Fajo do Penedo. From here we traverse back to Sao Vincente and the accommodation. This is one of the longer days of the retreat with the first half more of a run/hike as we head up to the central ridge-line of Madeira. With 1250m of ascent, we reach our highest point of the week, Pico de Jorge (1691m). After this, we start an undulating descent, picking up a few more peaks as we return to the villa. The afternoon will be free for rest and recovery. Dinner will be plentiful, nutritious and cooked by a member of the team.

Meals included: Breakfast, lunch and dinner

Madeira running

After an early breakfast, we transfer to the small town of Santana on the north-west coast. This will be the longest transfer of the trip due to the scenic but windy roads and will take approximately 45 minutes. Once here, we take a quick look at the local ‘casas tipicas’ before setting off on our final trail run of the week. Once again, we rise through the lush settings on a series of meandering trails. With the major climb out the way, we continue to rise and fall along the way. With 19km under the belt, we make our final short but steep descent on tired legs.

Reaching our destination Fajo do Penedo, we have a short transfer (15 minutes) back to Sao Vincente. Our final day of the trail running adventure is complete!

Meals included: Breakfast, lunch and dinner

Final day

This morning you can treat yourself to an extra hour or two in bed for a well-earned rest, before saying your final farewells and finishing the trip fitter than ever before no doubt. Until next time.

Meals included: Breakfast

Location Information

You need to book your own flights and arrive into Funchal airport. From here you can either rent a car from the airport, or take a taxi to the villa to meet the team and running buddies.

A car is advisable if you plan on exploring the area after your running day has ended.

Your villa style accommodation includes large communal areas both inside and out for relaxing and socialising. It’s located in the Sao Vicente region and has been selected for easy access to Funchal City and Madeira airport.

Most trail-heads are either from the villa or a short (20 mins transfer).


  • 6 nights villa style accommodation
  • All breakfasts, lunches and dinners as stated in the itinerary
  • 4 expertly guided trail runs
  • Stretch and strengthening classes
  • Training plan prior to departure


This is a small group with a maximum of 8 people. It runs with a minimum of 4 people.

The trail runs are expertly guided throughout. Rest assured, your guide is an experienced ultra-marathon runner and Qualified Leader & Outdoor First Aider.

The trip will be confirmed 8 weeks prior to departure. If people wish to book after this then it would be subject to availability.

Trail running: 85km over 4 days
Total ascent: 5500m
Duration: 4-5 hours per day
Grade: Demanding