Historic Levada Trails, Subtropical Forests, and Legendary Wine
Hiking the Isle of Madeira
Overview
Set in the cobalt blue waters of the Atlantic and warmed by the Gulf Stream, Madeira is an island of eternal spring, blanketed in lush laurel forests and topped by sharp volcanic peaks that sheer out of the sea. Our hiking journey explores the island’s many personalities as we walk ancient “levada” irrigation canals through green valleys and UNESCO-protected laurissilva forests, hike to crater lakes, take cobbled paths to red-roofed villages, and cross high trails above the sparkling Atlantic. Along the way, we’ll visit a producer of Madeira’s famous fortified wines, taste catch-of-the-day fish, and go dolphin and whale watching by private boat. This is the perfect way to celebrate Madeira’s beauty!
Arrive: Funchal, Portugal
Depart: Funchal, Portugal
Highlights
- Hike Madeira’s unique levada trails through subtropical forests
- Savor fresh seafood, explore red-roofed villages, hear evocative fado music
- Go dolphin and whale watching by private boat
- Explore impossibly picturesque Funchal, with its colorful homes
- Enjoy delightful hotels, including elegant Reid’s Palace, the Grand Dame of Funchal
Itinerary
After a spectacular coastal walk on the Ponta do São Lourenco trail, we hike our first levada, the Levada dos Maroços, and along an old trail that brings us to the north of the island. We stop by the town of Santana, with its triangular houses, and on one evening, we’ll sample Madeira’s wines at a private tasting.
A hike along the Levada Ponta do Pargo brings us through farmland with vistas of steep sea-facing cliffs and the shimmering waves of the Atlantic. The next day finds us hiking on the Paul da Serra, a high plateau that hosts an indigenous laurissilva forest, now a UNESCO World Natural Heritage Site. We'll taste wines and enjoy lunch and a vineyard tour at a winery at São Vicente, then drive through small coastal villages along a dramatic strip of land between sea and cliff, often referred to as the “Big Sur” of Madeira.
Our hike on the Royal Path, a trail in place before roads were built, brings us from a high saddle down through woodlands, below the cliffs of Pico Grande, and across a ridge to Boca da Corrida, with great views all the way. Our final hike is on a cobbled path through chestnut trees to the village of Curral das Freiras, followed by an afternoon of dolphin and whale watching by private boat. Depart on Day 8.
Accommodations
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
What the Trip is Like
This trip is rated Level 3+, Moderate, according to our trip grading system. We have five hiking days, varying from 2-8 hours of hiking a day. Our challenge day is strenuous; the trail is quite narrow and steep in places, with precipitous drop-offs and a degree of exposure. Please note that our daily hiking activities are weather-dependent. Based on their many years of experience here, our Trip Leaders always have wonderful alternate plans.
Average Hiking Day
- 5-6 miles
- 4 hours
- 1,240' ascent/descent
Challenge Day
- Day 6: 9 miles, 7-8 hours, 3,500' ascent/2,000' descent
Two of our hikes are along levadas, where the paths are well maintained and there is minimal altitude gain or loss. Others are on well-defined but rocky trails and involve a few thousand feet of ascent and descent.
The shape you’re in will be an important factor in your enjoyment of the trip. You must be fit and ready to walk. We strongly urge you to train for the trip with regular hiking, especially over hills or rough terrain, running, swimming, bicycling, or other sports exercise. You should wear sturdy, well-broken-in hiking boots for maximum comfort on the trail.
Madeira is a subtropical island. The south coast is the warmest and driest area and the mountains, rising to over 6,000 feet, are the coolest and wettest. We can expect pleasant temperatures of 58 to 66°F at the coast, but cooler temperatures up in the mountains. April is the start of the dry season, but rain is always a possibility; the monthly average is two inches.
All our hotels are chosen for their local history and central location. Because some of them are in historic buildings, the rooms may not conform to uniform standards, but we hope you will enjoy them for their charm and local color. Single rooms can be requested, but are not always available, due to the limited space in some of our hotels. If you require a single room, please make the request as early as possible. European single rooms are often smaller than US singles.
We travel the island by mini-bus, and the roads are very twisty in some places. The longest single drive is about one hour and 15 minutes.
Client Testimonials
"Wonderful trip in a beautiful place filled with fascinating people, delicious food, and amazing engineering (levadas, tunnels, and bridges)."
Barbara H.
Boston, MA
"Really a magical trip—and very well-organized!"
Clarissa M.
Tucson, AZ
"Madeira is a beautiful island and it really feels as though we experienced all the variety it had to offer. Learning about the history of the area was very interesting. It was a very enjoyable trip."
Jeanna F.
Paradise Valley, AZ
"Well-designed trip that combined some good hiking with getting a feel of the culture of the island."
Jeff L.
Sioux Falls, SD
"Excellent trip, itinerary, and flow. In one week we enjoyed a deep dive with Madeira and often off the beaten track. Great job of avoiding crowds. Paced just right. Gorgeous hotels, delectable meals, and plenty of wine. I especially liked the wide variety of hikes, from plunging coastal cliffs to Harry Potter-ish forests to climbs above the clouds atop Madeira's highest peak."
Sarah H.
San Francisco, CA
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Itinerary
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Trip Levels
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult.