Madeira · Sample itinerary
Peaks, levadas and island wine
- Length
- 11 nights
- Best for
- Active couples and friends
- Best time
- April to October
- Pace
- Active days, long dinners
Why I love this trip
Madeira is a Portuguese island in the Atlantic, closer to Morocco than to Lisbon, and one of the best places in Europe to walk. Ridge trails cross the peaks above the clouds, and hundreds of kilometres of levadas, old irrigation channels, wind through ancient laurel forest. In the evenings there is wine with five centuries of history and a food scene to match.
I plan it around three bases so every big hike starts close to your door: Funchal for wine and food, the wild north coast for the mountains, and the sunny south-west to finish. Summer brings the driest trails and clearest summit views, and in late summer you can join the grape harvest during the island’s wine festival.
- Days 1 to 3
Funchal
3 nights in Madeira’s wine and food capital
A private tasting and cellar tour at a historic wine lodge, a food walk from the Mercado dos Lavradores through the old town, and poncha, the island’s honey and lemon drink, in the fishing village of Câmara de Lobos. Walk your first levada above the city and dine anywhere from Michelin-starred rooms to traditional Madeiran tables.
- Days 4 to 7
Santana and the north coast
4 nights at Quinta do Furão, a hotel set in its own vineyard on the cliffs
The hiking heart of the trip: the sunrise ridge trail from Pico do Arieiro to Pico Ruivo, the island’s highest peak, the Caldeirão Verde levada through UNESCO-listed laurel forest, and the sea cliffs of São Lourenço. Between hikes, taste the estate’s own wines, visit a family winery on the terraces at Seixal, and eat espetada grilled on bay laurel.
- Days 8 to 11
Calheta and the south-west coast
4 nights at an oceanfront resort or boutique stay
The sunny side of the island. Hike to the waterfalls of 25 Fontes, try canyoning or kayaking, and swim in the calm summer sea. Taste rum and cane honey at a working mill, book a chef-led dinner on the coast, and end with fresh fish at sunset in Paul do Mar.
- Day 12
Fly home
About 45 minutes back to the airport.
Make it yours
This is a starting point, not a package.
I design every trip with trusted experts who live and work in the region, and I can change anything here: your dates, your pace, the hotels, or how long you stay in each place. Where I can, I’ll add preferred-partner perks like daily breakfast and hotel credits to your stays. Pricing depends on season and the hotels you choose, so I’ll prepare a personal proposal for you.
Ready when you are