Hiking the Isle of Madeira

Historic Levada Trails, Subtropical Forests, and a Legendary Wine


Set in the cobalt blue waters of the Atlantic and warmed by the Gulf Stream, the island of Madeira is a world of its own, blanketed in lush green laurel forests and topped by sharp volcanic peaks that sheer out of the sea. Between mountains and shore live a unique and colorful people whose cultural roots stem from ships sent by Portugal’s Prince Henry the Navigator in the early 1400s. Our special hiking journey explores the island’s many personalities and terrain. Walking “levada” trails along ancient irrigation canals through green valleys and UNESCO-protected laurissilva forests rich in mosses and lichens, we discover the island’s interior landscapes, and from high vistas, peer into deep gorges, over distant red-roofed villages, and all the way to the sparkling Atlantic. Along the way, we’ll visit a producer of Madeira’s famous fortified wines, taste catch-of-the-day fish, explore coastal villages, and go dolphin and whale watching by private boat. Madeira Island is a rare wonder and our journey is the perfect way to celebrate its beauty!

Itinerary at a Glance

Days 1-3
Funchal, Madeira / Fado Music / Hike the Levada do Furado

Hike at Ponta do Sao Lourenco, then roam the Farmers’ Market and listen to Portugal’s evocative Fado music at dinner. Hike the Levado do Furado into indigenous laurel forests alive with birdsong, then stop by the town of Santana, with its triangular houses. After we watch an antique steam-driven machine crush sugar cane, we’ll try the local rum, then sample Madeira’s wines at at a private Sommelier-led tasting.

Casa Velha do Palheiro
Funchal, Portugal
Days 1 to 3 (3 nights)
Days 4-5
Levada Nova da Calheta / Paul da Serra do Paul / Vineyard Tour

A hike along the Levada Nova da Calheta brings us through farmland where many of the regional vegetables are grown. The next day finds us hiking on the Paul da Serra do Paul through a laurissilva forest, classified a UNESCO World Natural Heritage Site. We’ll taste wines and enjoy lunch and a vineyard tour at a winery at Sao Vicente before a drive through small coastal villages set on the narrow strip of land between sea and cliff, often referred to as the “Big Sur” of Madeira.

Aqua Natura Madeira Hotel
Porto Moniz, Portugal
Days 4 to 5 (2 nights)
Days 6-8
The Royal Path / Hike to Curral das Freiras / Dolphin and Whale Watching

On Day 6, we hike the Royal Path, a trail used long before roads were built. We follow it from a high saddle down through woodlands, below the rugged cliffs of Pico Grande, and across a high ridge to Boca da Corrida, with great views all the way. After our descent on a cobbled path through chestnut trees to the village of Curral das Freiras, we head out by private boat for dolphin and whale watching. Depart on Day 8.

Reid's Palace Hotel
Funchal, Portugal
Days 6 to 7 (2 nights)



Hike Madeira’s unique levada trails through subtropical forests and below volcanic mountains
Follow a spectacular ridge trail to Madeira’s highest point at 6,100 feet
Savor fresh-caught seafood and exotic fruits, explore red-roofed villages, hear evocative Fado music
Learn about Madeira’s centuries-old wine heritage
Go dolphin and whale watching by private boat
Explore impossibly picturesque Funchal, with its colorful homes
Enjoy delightful hotels, including a historic estate nestled in manicured gardens and the elegant Reid’s Palace, the Grand Dame of Funchal


Length: 8 days
Cost From: $4795  
Arrive: Funchal, Portugal
Depart: Funchal, Portugal
Lodging: 7 nights hotels
Meals: All meals included except 1 lunch and 2 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Cultural Adventures, Hiking / Trekking
Trip Level:

5 hiking days on moderate to strenuous trails, some steep sections, 2-7 hours a day