A WORLD CLASS TRAIL RUNNING ADVENTURE
ON EUROPE’S MOST DRAMATIC ISLAND

WHY MADEIRA?

VOLCANIC BEAUTY, UNESCO LANDSCAPES, YEAR-ROUND SUNSHINE

The archipelago of Madeira is situated in the north Atlantic Ocean, southwest of Portugal. It is famous for its wine, local food, historical and cultural value, immensely beautiful and lush landscape, and of course, incredible mountain trails that ‘Trail Run Adventures’ fell in love with. We will explore all of the main corners of the island, the high points of Pico Ruivo and its neighbouring peaks, ancient levadas, waterfalls, tunnels, sandy and rocky beaches, and the famous city of Funchal.

Trail running vacations
RUN THE TRAILS: Explore world-class trails across Madeira’s most breathtaking landscapes — from lush levadas and dramatic ridgelines to rugged cliffs and ancient tunnels. Each run is pace-supported, with guided options tailored to suit all fitness levels.
All inclusive trail running holidays
ALL INCLUSIVE: Relax in stunning ocean-view accommodation perched on a cliff edge, with all meals included. From fresh local cuisine and recovery-ready amenities, to all transport and activities on the island, everything is taken care of so you can focus on the adventure.
Trail running adventure activities
BEYOND THE TRAILS: Activities for the Adventure seekers — canyoning, surf lessons, yoga, and a private catamaran with whale and dolphin watching. You can even bring a spouse or friend who doesn’t run; there are lots of options for activities.

ADVENTURE ITINERARY

  • Meals: Dinner

    Run: ~10km, coastal

    Activities:

    • Arrival in Funchal, shuttle to hotel. *Please choose flight times that allow you to arrive by early afternoon, so that you can join the evening run at 5pm and dinner/briefing at 7pm.

    • Check-in to hotel from 2pm

    • Wine tour and briefing

    • Dinner at Hotel

  • Meals: Breakfast, Lunch + Dinner

    Run: ~23km, Madeira’s highest peak, Pico Ruivo.

    Starting at Teixeira, running up high above the clouds to Pico Ruivo and then following the unique pathway connecting to Pico Areeiro. Arrive at the restaurant for any extra energy bites you need to get you to the finish. Amazing to see the 360 views of the entire island!

    Activities:

    • Breakfast Buffet

    • Evening Yoga/Stretch/Core strength

    • Dinner at Hotel

  • Meals: Breakfast + Dinner

    Run: ~20km, coastal ridge

    Activities:

    • Breakfast Buffet

    • Lunch at a local restaurant after our run (*Additional Cost)

    • Surf Lessons (all gear is provided)

    • Evening Yoga/Stretch/Core strength

    • Dinner at Hotel

  • Meals: Breakfast, Lunch + Dinner

    Run: Today we Canyon!

    Activities:

    • Breakfast Buffet

    • Canyoning 3-4 hours (all gear is provided)

    • Evening Yoga/Stretch/Core strength

    • Dinner at Hotel

  • Meals: Breakfast, Lunch + Dinner

    Run: ~12km, stunning Levadas

    Activities:

    • Breakfast Buffet

    • Shuttle to Funchal

    • Explore Funchal

    • Board a luxurious private Catamaran for Whale/Dolphin watching, afternoon tea and drinks, and water activities.

    • Dinner at Hotel

  • Meals: Breakfast, Lunch + Dinner

    Run: Santana Vertical Kilometre Race, or REST DAY

    Activities:

    • Breakfast Buffet

    • *Today you have the option to do the Vertical Kilometer race as well!

    • Rest Day

    • Optional massage (Additional Cost)

    • Optional: Visit other parts of the island today (Additional Cost)

    • Pick up race packets

    • Lunch at Hotel

    • Dinner at Hotel

  • Meals: Breakfast, Lunch + Dinner

    Run: Race Day! Choose your distance.

    Activities:

    • Breakfast Buffet

    • Shuttles to and from races.

    • Race!!! Start times differ depending on distance.

    • Today’s lunch will be a pasta party at the race finish.

    • Goodbye dinner and drinks at the Hotel

  • Meals: Breakfast

    Time to say goodbye…

    • Shuttles to the Airport

    • Or stay in Madeira for extra night/s at your own expense. We can recommend activities!

ULTRASKYRUNNING MADEIRA - CHOOSE YOUR RACE DISTANCE

WHAT TO EXPECT:

  • Our trails are subject to change as we tailor our days to provide you with the best possible experience under daily conditions. However, you can expect to run from 1 hour to 4 hours, or 10-23km each day, with the longer trails being a combination of hiking uphill and trail running. We frequently stop to re-group, catch our breath, take photos, and soak in the beautiful scenery, so the distances are not run non-stop.

  • 3 (Moderate Difficulty)

    This trip is rated a 3, for moderate difficulty. Some of the runs can be cut short, but some of the terrain is steep and technical. Everyone will be able to run their own pace, so the trip is suitable for anyone comfortable with technical terrain. You should be regularly running 10km+ to prepare for this trip.

  • Adventure Travel: As we base ourselves at the stunning Quinta du Furão, Shuttles will transport the group around the island to the various trails and activities.

    Flights: Once we have confirmed you can book flights, you will fly to Funchal (FNC), Madeira. Book a window seat if possible, as the views are spectacular flying in!

    Airport Shuttles: Complimentary shuttles will be provided for airport pickup and drop-off, and confirmed 24 hours prior.

  • Madeira’s official language is Portuguese and the currency is the Euro (€). While English is widely understood in tourist areas, learning a few local phrases goes a long way. To greet someone, say “Olá” (hello), and to express gratitude, say “Obrigado” if you're male, or “Obrigada” if you're female.

  • Your home will be the beautiful Quinta do Furão, a cliff-top boutique hotel offering twin-share accommodation (single upgrade available), with stunning ocean views, a hot tub, pool, gym, cocktail bar, restaurants, and cellar door, all set in lush vineyard surroundings ideal for relaxation and recovery.

  • Madeira’s subtropical climate offers year-round sunshine and mild temperatures, ranging from lows of 14°C to highs of 25°C on average. Perfect for trail running any time of year!

  • Breakfast: Extensive and sumptuous buffet breakfast at the hotel.

    Lunch: Lunches vary depending on the daily itinerary, from pizza, to ample packed lunches, and one or two offsite restaurant lunches at an additional cost.

    Dinner: Nightly 3 course dinners at the hotel restaurant, featuring both indoor and outdoor dining with stunning sea and mountain views. The menu combines traditional Madeiran flavours with international dishes, emphasising local and organic ingredients, and is a definite highlight!

THE ADVENTURE INVESTMENT

$2995 USD

  • $500 non refundable deposit required to secure your place. The deposit can be transferred to another adventure, and will be refunded in full if the adventure doesn’t go ahead.

  • Remaining balance due by 90 days prior to adventure. Registrations made within 90 days of the trip date must be paid in full.

    • Airport transfers and all transportation while in Madeira

    • Accommodation at the stunning Quinta do Furao (based on twin/double shared rooms. Single room upgrade is $800

    • Breakfast buffet, packed lunches, and dinner at the delicious Quinta do Furao restaurant

    • All dietary requirements can be catered to

    • Equipment for all adventures

    • Whale/Dolphin watching tour on a private Catamaran

    • Local guides

    • Yoga/Stretch/Core Strength

    • A guaranteed great time!

  • Flights (Please do NOT make travel arrangements until we notify you that the group size has met the minimum)

    • Personal travel and medical insurance

    • Offsite restaurant Lunches

    • Alcohol and other drinks

    • Additional snack foods, race food (gels, bars, electrolytes etc)

    • Personal spending - souvenirs etc.

    • Massages (can be arranged at the hotel)

    • Extra days before or after the trip

    • Tips

    • Laundry service (available at hotel $$)

FREQUENTLY ASKED QUESTIONS & PACKING LIST

WHAT OUR CUSTOMERS ARE SAYING

“In June, I went on my first trail running vacation with Trail Run Adventures in Madeira, and it was nothing short of extraordinary. From the meticulous planning and support from Anna and Braz, to the awe-inspiring trails we ran each day, every element of the trip was seamless.”
— Kylie M, June 2025